Found 11 structures.
Displayed structures from 1 to 11
Expand all compounds
Collapse all compounds
Show all as text (SweetDB notation)
Show all graphically (SNFG notation)
1. Compound ID: 20822
Structure type: oligomer
C27H30O16
Trivial name: rutin, rutoside, rutin, quercetin rutinoside, rutoside, quercetin 3-O-rutinose, quercetin-3-O-rutinoside, quercetin 3-O-rutinoside
Compound class: saponin glycoside, glycoside, flavonoid glycoside, flavonol glycoside, flavone glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144144,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8312
Patil MP, Patil RH, Maheshwari VL "Biological activities and identification of bioactive metabolite from endophytic Aspergillus flavus L7 isolated from Aegle marmelos" -
Current Microbiology 71(1) (2015) 39-48
Aegle marmelos, a well-known Indian plant with medicinal and religious importance, has been extensively used in Indian traditional medicine. The present study aimed to isolate, identify, and evaluate the biological activities of endophytic fungi from A. marmelos. One of the isolates, labeled as L7, was identified as Aspergillus flavus using morphology and ITS gene sequence. Total phenolic and flavonoid contents in the culture filtrate were found to be 65.77 mg GAE/ml and 158.33 mg quercetin/ml of crude extract, respectively. The extract showed excellent antimicrobial activity against common human bacterial and fungal pathogens. The test extract at 700 µg/ml, which notably reduced the concentration of DPPH-free radical as percent DPPH scavenging activity, was found to be the highest (64.53 %). The extract, at the concentration of 2 mg/ml, produced 70 % inhibition of hemolysis of RBCs compared to 78 % produced by standard drug (Ibuprofen). Chemical profiling of the fermented extract using TLC followed by UV and FTIR revealed the presence of flavonoids. The HPLC analysis confirmed the presence of bioflavonoid rutin in the extract. To the best of our knowledge, this is the first report on production of bioactive flavonoid by endophytic Aspergillus flavus obtained from A. marmelos and its pharmaceutical potential. In conclusion, the endophytic Aspergillus flavus obtained from the A. marmelos could be explored as an economic and potential natural resource with diverse pharmaceutical and biological activities
endophytic fungus, Aspergillus flavus, Aegle marmelos, rutin
NCBI PubMed ID: 25860867Publication DOI: 10.1007/s00284-015-0805-yJournal NLM ID: 7808448Publisher: Springer International
Correspondence: vlmaheshwari@rediffmail.com
Institutions: Department of Microbiology and Biotechnology, R. C. Patel Arts, Commerce and Science College, Shirpur, India, Department of Biochemistry, School of Life Sciences, North Maharashtra University, Jalgaon, India
Methods: IR, PCR, DNA techniques, TLC, biological assays, HPLC, UV, extraction, cell growth, antioxidant activities, antibacterial assay, bioinformatic analysis (BLASTp), evaporation, antifungal activity test, Folin phenol reagent method
- Article ID: 8797
Yan L, Zhao HB, Zhao XX, Xu XG, Di YC, Jiang CM, Shi JL, Shao DY, Huang QS, Yang H, Jin ML "Production of bioproducts by endophytic fungi: chemical ecology, biotechnological applications, bottlenecks, and solutions" -
Applied Microbiology and Biotechnology 102(15) (2018) 6279-6298
Endophytes are microorganisms that colonize the interior of host plants without causing apparent disease. They have been widely studied for their ability to modulate relationships between plants and biotic/abiotic stresses, often producing valuable secondary metabolites that can affect host physiology. Owing to the advantages of microbial fermentation over plant/cell cultivation and chemical synthesis, endophytic fungi have received significant attention as a mean for secondary metabolite production. This article summarizes currently reported results on plant-endophyte interaction hypotheses and highlights the biotechnological applications of endophytic fungi and their metabolites in agriculture, environment, biomedicine, energy, and biocatalysts. Current bottlenecks in industrial development and commercial applications as well as possible solutions are also discussed.
endophyte, biocontrol, mutualism, interaction benefit, adversity tolerance, nutrient acquisition, bioproduct
NCBI PubMed ID: 29808328Publication DOI: 10.1007/s00253-018-9101-7Journal NLM ID: 8406612Publisher: Springer
Correspondence: Shi JL
Institutions: Key Laboratory for Space Bioscience and Biotechnology, School of Life Sciences, Northwestern Polytechnical University, Xi’an, China
- Article ID: 8880
Kosanić M, Ranković B, Stanojković T, Radović-Jakovljević M, Ćirić A, Grujičić D, Milošević-Djordjević O "Craterellus cornucopioides edible mushroom as source of biologically active compounds" -
Natural Product Communications 14(5) (2019) ID 19843610
Here we determined the phenolic compounds and antioxidant, antimicrobial, genotoxic, and anticancer potential of edible mushrooms Craterellus cornucopioides. The phytochemical analysis was evaluated using high-performance liquid chromatography. Antioxidant activity was evaluated by free radical scavenging, superoxide anion scavenging, and reducing power. Craterellus cornucopioides extract had potent antioxidant activity. Further, the antimicrobial potential was determined by a microdilution method, where minimum inhibitory concentration values ranged from 0.1 to 10 mg/mL. Genotoxic potential was determined by cytokinesis block micronucleus test. The separate treatment did not show genotoxic effect, whereas the combined treatment with mitomycin C significantly reduced the micronuclei frequency in a dose-dependent manner. The highest concentration significantly reduced nuclear division index in comparison to untreated human peripheral blood lymphocytes, whereas in combined treatment, the extract did not significantly affect this parameter. Finally, the cytotoxic activity was tested using microculture tetrazolium test where measured IC50 values ranged from 65.5 to 131.7 μg/mL.
HPLC, antimicrobial, Antioxidant, cytotoxic, genotoxic, mushroom extract
Publication DOI: 10.1177/1934578X19843610Journal NLM ID: 101477873Publisher: Natural Product Communications
Correspondence: marijanakosanic@yahoo.com
Institutions: Faculty of Science, Department of Biology and Ecology, University of Kragujevac, Serbia, Institute of Oncology and Radiology of Serbia, Belgrade, Serbia, Faculty of Science, Department of Chemistry, University of Kragujevac, Serbia
Methods: HPLC, extraction, CC, antioxidant activities, cytotoxicity assay, antimicrobial assay
- Article ID: 8901
Wagay JA, Nayik GA, Wani SA, Mir RA, Ahmad MA, Rahman QI, Vyas D "Phenolic profiling and antioxidant capacity of Morchella esculenta L. by chemical and electrochemical methods at multiwall carbon nanotube paste electrode" -
Journal of Food Measurement and Characterization 13 (2019) 1805–1819
The present investigation was carried out to know the aboriginal usage of Morchella esculenta L. as an ethnomedicinal food by tribals of Kashmir, an extreme northern state of India for curing of arthritis, osteoporosis, general bone weakness and cure child labour pain and post menopause pain of women. The average long-life expectancy (~80 years) and delayed aging ensured the abundant use of M. esculenta L. as the bases of their daily foods as well as their traditional medicine. The antioxidant character of this mushroom was carried out by chemical and electrochemical assays. The chemical assay was done by DPPH, nitric- oxide, super-oxide scavenging and reducing power while as, electrochemical assay was done by cyclic voltammetry (CV) and differential pulse voltammetry (DPV) using multi-wall carbon nanotube paste electrode (MWCNTPE) at 0.02 M acetate buffer (pH 4.5). The phenolic profiling of the mushroom was evaluated through Folin–Ciocalteu reagent using gallic acid/ascorbic acid as standard which were qualified and quantified by HPLC-UV technique, respectively. The IC50 values found were 57.02 µg/ml, 58.02 µg/ml and 40.01 µg/ml for DPPH, nitric-oxide and superoxide. The electrochemical results have shown one oxidation potential at 1.12 V and positive potential at 1.119±0.01 V in CV and 1.19 V in DPV. DPV at superoxide radical scavenging level of mushroom at dropping mercury electrode (DME) in 0.1 M KCl, produced a reduction peak potential at −0.160 V. HPLC-UV have confirmed the presence of eight phenolic compounds namely, p-coumaric acid, tocopherol, catechol, rutin, hyperoside, quercetin, ellagic acid and cinnamic acid with quercetin at highest percentage (169.76%).
Antioxidant, Morchella esculenta, electrochemical, phenolic compounds
Publication DOI: 10.1007/s11694-019-00099-3Publisher: Springer
Correspondence: Wagay JA
Institutions: Department of Plant Science, Agriculture and Rural Transformation, University of Gondar, Gondar, Ethiopia, Department of Food Science and Technology, GDC Shopian, Srinagar, India, Department of Botany, GDC Shopian, Srinagar, India, Department of Chemistry, Integral University, Lukhnow, India, Department of Botany, Dr. Harisingh Gour Central University, Sagar, India
Methods: extraction, antioxidant activities, spectrophotometry, evaporation, HPLC-UV, Folin phenol reagent method, cyclic voltammetry
- Article ID: 9180
Oyinloye BE, Onikanni SA, Ajiboye BO "Structure-based docking studies of monoamine oxidase against bioactive compounds from Trametes pubescens in the treatment of neurodegenerative diseases" -
PharmacologyOnline 2 (2020) 337-347
This study was projected to assess the structure-based docking studies of monoamine oxidase against bioactive compounds from Trametes pubescens fruiting body extract in the treatment of neurodegenerative diseases. In this study, five bioactive compounds were acknowledged monoamine oxidase inhibitors acquired from T. pubescens fruiting body extract which were retrieved by the PubChem database. Molecular docking investigations in addition to ADME studies were carried out using different bioinformatics tools. The findings demonstrated that epigallocatechin gallate (-11.770 kcal/mol), caffeic acid (-7.010 kcal/mol) and gallic acid (-6.984 kcal/mol) have the highest molecular docking scores than the coligand used (zonisamide) (-6.328 kcal/mol). Whereas, naringin (-4.514 kcal/mol) and rutin hydrate (-3.833 kcal/mol) have the lowest molecular binding scores when compared to the coligand. However, only gallic and caffeic acids have good ADME results and compared favourably with the coligand. Hence, it can be deduced from this study that gallic and caffeic acids can function as a possible therapeutic agent in the treatment of neurodegenerative diseases better than zonisamide (coligand).
zonisamide, molecular binding score, ADME, coligand
Journal NLM ID: 101266394WWW link: https://pharmacologyonline.silae.it/files/archives/2020/vol2/PhOL_2020_2_A033_Oyinloye.pdfPublisher: Salerno: SILAE
Correspondence: Ajiboye BO
; Ajiboye BO
Institutions: Phytomedicine, Biochemical Toxicology and Biotechnology Research Laboratory, Department of Biochemistry, Afe Babalola University, Ado-Ekiti, Nigeria, Biotechnology and Structural Biochemistry (BSB) Group, Department of Biochemistry and Microbiology, Faculty of Science and Agriculture, University of Zululand, KwaDlangezwa, South Africa
Methods: molecular modeling
- Article ID: 9196
de Britto J, Manickam VS, Gopalakrishnan S, Ushioda T, Tanaka N "Determination of aglycone chirality in dihydroflavonol" -
Chemical and Pharmaceutical Bulletin 43(2) (1995) 338-339
Three dihydroflavonol glycosides, 3-O-α-L-rhamnosides of (2S,3S)-, (2R,3R)- and (2R,3S)-5,7,3',4'-tetrahydroxydihydroflavonol, were isolated from Sphaerostephanos arbuscula as the first example of dihydroflavonols from ferns. Aglycone chirality was determined by 1H-NMR data.
1H-NMR, astilbin, Sphaerostephanos arbuscula, dihydroflavonol, chirality determination, fern
Publication DOI: 10.1248/cpb.43.338Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Department of Botany, St. Xavier's College (Autonomous), Palayamkottai, India, Department of Chemistry, Manonmaniam Sundaranar University, Tirunelveli, India, Faculty of Pharmaceutical Sciences, Science University of Tokyo, Tokio, Japan
Methods: 13C NMR, 1H NMR, EI-MS, IR, acid hydrolysis, GLC, HPLC, UV, extraction, optical rotation measurement, CD, CC, melting point determination, precipitation, derivatization
- Article ID: 9732
Ern PTY, Quan TY, Yee FS, Yin ACY "Therapeutic properties of Inonotus obliquus (Chaga mushroom): A review" -
Mycology 15(2) (2024) 144-161
Inonotus obliquus, also known as Chaga, is a medicinal mushroom that has been used for therapeutic purposes since the sixteenth century. Collections of folk medicine record the application of Chaga for the treatment of diseases such as gastrointestinal cancer, diabetes, bacterial infection, and liver diseases. Modern research provides scientific evidence of the therapeutic properties of I. obliquus extracts, including anti-inflammatory, antioxidant, anticancer, anti-diabetic, anti-obesity, hepatoprotective, renoprotective, anti-fatigue, antibacterial, and antiviral activities. Various bioactive compounds, including polysaccharides, triterpenoids, polyphenols, and lignin metabolites have been found to be responsible for the health-benefiting properties of I. obliquus. Furthermore, some studies have elucidated the underlying mechanisms of the mushroom's medicinal effects, revealing the compounds' interactions with enzymes or proteins of important pathways. Thus, this review aims to explore available information on the therapeutic potentials of Inonotus obliquus for the development of an effective naturally sourced treatment option
Anticancer, anti-inflammatory, Inonotus obliquus, medicinal mushroom, therapeutic properties, anti-diabetic
NCBI PubMed ID: 38813471Publication DOI: 10.1080/21501203.2023.2260408Journal NLM ID: 101523848Publisher: Abingdon, Oxon: Taylor & Francis
Correspondence: adelineyokeyin.chia@taylors.edu.my
Institutions: School of Biosciences, Faculty of Health & Medical Sciences, Taylor's University, Subang Jaya, Selangor, Malaysia, Department of Molecular Medicine, Faculty of Medicine Building, University of Malaya, Kuala Lumpur, Malaysia
- Article ID: 10655
Neville HA, Bohm BA "Flavonoids of Umbellularia californica" -
Phytochemistry 36 (1994) 1229-1231
The vacuolar flavonoid profile of Umbellularia californica consists of 3-O-mono-, di- and triglycosides of kaempferol, quercetin and isorhamnetin together with eriodictyol 7-O-glucoside. The leaf exudate contained no flavonoids but did exhibit a small amount of scopoletin. The two growth forms of this species, a shrubby form from dry habitats and a coastal forest tree, exhibited identical flavonoid profiles. These observations were taken to indicate that the flavonoid profile of this species became established before the two growth forms differentiated. The flavonol profile of Umbellularia is consistent with profiles reported for other members of the Lauraceae.
variation, flavonoids, flavonol glycosides, Umbellularia californica, Lauraceae
Publication DOI: 10.1016/S0031-9422(00)89642-9Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Botany, University of British Columbia, Vancouver, British Columbia, Canada
Methods: TLC, MS, UV
- Article ID: 10714
Sekine T, Arai Y, Ikegami F, Fujii Y, Shindo S, Yanagisawa T, Ishida Y, Okonogi S, Murakoshi I "Isolation of camelliaside C from 'tea seed cake' and inhibitory effects of its derivatives on arachidonate 5-lipoxygenase" -
Chemical and Pharmaceutical Bulletin 41 (1993) 1185-1187
A new flavonol glycoside, camelliaside C, was isolated from "tea seed cake" prepared from the defatted seeds of Camellia sinensis O. KUNTZE. The structure was determined as kaempferol 3-O-β-D-galactopyranosyl-(1→2)-β-D-glucopyranoside by spectroscopic methods (FAB-MS, UV, IR, ^1H- and ^<13>C-NMR) and the enzymatic transformation of camelliaside C to astragalin. Camelliaside C showed an inhibitory effect on the arachidonate 5-lipoxygenase of RBL-1 cells (IC_<50> : 1.4×10^<-4> M) as did camelliaside A and B isolated from the same product.
Camellia sinensis, Theaceae, camelliaside C, arachidonate 5-lipoxygenase inhibitor, tea seed cake
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003630580Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Chiba University, Japan, Tsumura Research Institute of Pharmacology, Japan, Faculty of Pharmacy, Chiang Mai University, Thailand
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, acid hydrolysis, HPLC, enzymatic digestion, biological assay
- Article ID: 10744
Ofman DJ, Markham KR, Vilain C, Molloy BPJ "Flavonoid profiles of New Zealand kauri and other species of Agathis" -
Phytochemistry 38 (1995) 1223-1228
This paper describes the flavonoid constituents in Agathis australis from a wide geographic range and completes a comprehensive survey of the flavonoid chemistry/chemotaxonomy of New Zealand conifers begun in 1984. Flavonol 3-O-glycosides and biflavones of the cupressuflavone and agathisflavone types are shown to be the predominant flavonoids. NMR data for these biflavones with varying degrees of methylation are presented for the first time. The flavonoid profiles of A. australis and three other species of Agathis show a high level of uniformity, and in this respect are closely related.
chemotaxonomy, flavonoids, Agathis australis, Araucariaceae, biflavonoids, cupressuflavone, agathisflavone
Publication DOI: 10.1016/0031-9422(94)00783-PJournal NLM ID: 0151434Publisher: Elsevier
Institutions: New Zealand Institute for Industrial Research and Development, Lower Hutt, New Zealand, Manaaki Whenua-Landcare Research, Lincoln, New Zealand
Methods: 13C NMR, 1H NMR, TLC, LSI-MS, UV, 2D-PC
- Article ID: 10888
Bilia AR, Cecchini C, Marsili A, Morelli I "Coumarins and other constituents of Prunus prostrata" -
Journal of Natural Products 56 (1993) 2142-2148
From the aerial parts of Prunus prostrata (Rosaceae), the following new compounds were isolated: 5-(b-D-glucopyranosyloxy)-2-(3-hydroxybutyl)-l,3,3-trimethylcyclohexene [1], 4-(b-D-glucopyranosyloxy)-3-(3-methyl-2-butenyl)benzoic acid [2], fraxinol 6-b-D-galactopyranoside [3], and 6,7-dihydroxy-5-methoxycoumarin 6-b-D-glucopyranoside [4]. Their structures were established by means of fabms and a combination of homo- and hetero-nuclear 2D nmr techniques. Twelve known compounds, never previously isolated from this genus, were also found in this plant.
Publication DOI: 10.1021/np50102a017Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Institutions: Dipartimento di Chimica Bioorganica, Universita di Pisa, Pisa, Italy, Azienda Foreste Demaniali Regione Sardegna, Nuoro, Italy
Methods: 13C NMR, 1H NMR, FAB-MS, TLC, acid hydrolysis, CC
- Article ID: 10901
Kizu H, Shimana H, Tomimori T "Studies on the constituents of Clematis species. VI. The constituents of Clematis stans Sieb. et Zucc" -
Chemical and Pharmaceutical Bulletin 43(12) (1995) 2187-2194
From the roots of Clematis stans three new oleanane-type triterpenoid saponins named clemastanoside A, B and C, and two new lignan glycosides named clemastanin A and B, have been isolated together with three known triterpenoid saponins, huzhangoside B, C and D, and three known lignan glycosides, (+)-lariciresinol 4-O-β-D-glucopyranoside, (+)-lariciresinol 4'-O-β-D-glucopyranoside and (+)-pinoresinol 4,4'-O-bis-β-D-glucopyranoside. In addition, from the leaves, four new oleanane-type triterpenoid saponins, named clemastanoside D, E, F and G, have been isolated together with five known triterpenoid saponins, hederasaponin B, kizutasaponin K_<12>, huzhangoside B, sieboldianoside B and huzhangoside D, and three known flavonoids, isoquercitrin, rutin and quercetin 3-O-β-D-glucuronopyranoside. The structures of the new compounds were elucidated based on chemical and physicochemical evidence as follows : clemastanoside A, 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl oleanolic acid 28-O-(4-O-acetyl)-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (terminal rhamnosyl 4-O-acetate of huzhangoside B); clemastanoside B and C, 3-O-β-D-xylopyranosyl- and 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, respectively; clemastanoside D, 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester; clemastanoside E, F and G, terminal rhamnosyl 4-O-, 3-O- and 2-O-acetate of 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamno-pyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, respectively; clemastanin A, (7S, 8R)-3-methoxy-3', 4,9,9'-tetrahydroxy-4', 7-epoxy-5', 8-lignan 3'-O-β-D-glucopyranoside; clemastanin B, (+)-lariciresinol 4,4'-O-bis-β-D-glucopyranoside.
Ranunculaceae, lignan glycoside, Clematis stans, oleanolic acid bisdesmoside, hederagenin bisdesmoside, quercetin glycoside
NCBI PubMed ID: 8582022Publication DOI: 10.1248/cpb.43.2187Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Hokuriku University, Japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, acid hydrolysis, GLC, methanolysis, HPLC, alkaline hydrolysis, UV, enzymatic digestion, CD, HR-FAB-MS
- Article ID: 10940
Budzianowski J, Skrzypczak L "Phenylpropanoid esters from Lamium album flowers" -
Phytochemistry 38 (1995) 997-1001
Two phenylpropanoid glycosides, a new one, lamalboside (2R-galactosylacteoside) and the known acteoside, the flavonol p-coumaroylglucoside, tiliroside, 5-caffeoylquinic acid (chlorogenic acid), along with rutoside and quercetin and kaempferol 3-O-glucosides were isolated from the flowers of Lamium album. Esters of glycosides were obtained as mixtures of trans/cis isomers. The presence of flavonoid p-coumaroylglucosides links Lamium to other members of the subfamily Lamioideae.
phenylpropanoid glycosides, flowers, Lamiaceae, Lamium album, acylated flavonoids, lamalboside, 2R-galactosylacteoside, trans- and cis-tiliroside, trans/cis isomers
NCBI PubMed ID: 7766391Publication DOI: 10.1016/0031-9422(94)00727-BJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Pharmaceutical Botany, K. Marcinkowski Academy of Medicine, Poznań, Poland
Methods: 13C NMR, 1H NMR, TLC, acid hydrolysis, UV, CC
- Article ID: 10945
Xiong Q, Shi D, Mizuno M "Flavonol glucosides in pericarps of Zanthoxylum bungeanum" -
Phytochemistry 39 (1995) 723-725
Two new flavonol glucosides, viz. quarcetin 3′,4′-dimethyl ether 7-glucoside and tamarixetin 3,7-bis-glucoside, together with hyperin, quercetin, quercitrin, foeniculin, isorhamnetin 7-glucoside, rutin, 3,5,6-trihydroxy-7,4′-dimethoxyflavone, arbutin, sitosterol β-glucoside, l-sesamin and palmitic acid were isolated from the pericarps of Zanthoxylum bungeanum. Their structures were established by spectroscopic and spectrophotometric methods.
pericarp, Zanthoxylum bungeanum, flavonol glycosides, Rutaceae, quercetin 3′, 4′-dimethyl ether 7-glucoside, tamarixetin 3, 7-bis-glucoside
Publication DOI: 10.1016/0031-9422(94)00965-VJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Pharmacognosy, Gifu Pharmaceutical University, Gifu, Japan, Department of Pharmacognosy, School of Pharmacy, Shanghai Medical University, Shanghai, China
Methods: 13C NMR, 1H NMR, UV, CC
- Article ID: 10977
Habermehl GG "Poisonous plants of Brazil" -
Toxicon 32 (1994) 143-156
Poisonous plants are a serious problem for cattle breeding in Latin America. Owing to the extensive pastural agriculture it is not possible to exterminate such plants. Apart from the considerable financial loss to individual farmers and the national economy owing to dead animals, there is the important question of how far the meat and milk of chronically poisoned animals are a health risk for humans. The toxins of the most important toxic plants from Brazil are described.
NCBI PubMed ID: 8153954Publication DOI: 10.1016/0041-0101(94)90103-1Journal NLM ID: 1307333Publisher: Pergamon Press for International Society On Toxinology
Institutions: Department of Chemistry, Veterinary University, Hannover, F.R.G
- Article ID: 11097
Ma YT, Chuang JI, Lin JH, Hsu FL "Phenolics from Acalypha indica" -
Journal of the Chinese Chemical Society = Zhongguo hua hsueh hui hui zhi 44(5) (1997) 499-502
Two novel hydrolysable tannins, potassium brevifolincarboxylate and acaindinin, together with eight known tannins-1-O-galloyl-β-D-glucose, 1,2,3,6-tetra-O-galloyl-β-D-glucose, corilagin, geraniin, acetonylgeraniin A, euphormisin M-2, repandusinic acid A, and chebulagic acid, as well as two flavonoid glycosides-quercetin 3-O-β-D-glucoside and rutin, were isolated from Acalypha indica. Their structures were elucidated on the basis of chemical and spectroscopic evidence.
flavonoid, Euphorbiaceae, Acalypha indica, Phenolic;, Hydrolysable tannin, Potassium brevifolincarboxylate, Acaindinin
Publication DOI: 10.1002/jccs.199700075Journal NLM ID: 16210600RPublisher: Taipei: Chinese Chemical Society
Institutions: Department ofBiochemistry, Taipei Medical College, Taipei. Taiwan, R.O.C.
Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS
- Article ID: 11123
Aqil M, Khan IZ, Otukoyoung EE "Three flavonol glycosides from Ricinus communis" -
Bulletin of the Chemical Society of Ethiopia 11(1) (1997) 51-53
Chemical investigations on the roots of ricinus communis resulted in the isolation and characterization of a novel flavonol glycoside, kaempferol 3-O-β-D-[6'''-O-acetylglucopyranosyl [1→3)-β-D-galactopyranoside] for which the trivial name ricinitin is proposed. The structure of ricinitin was established on the basis of chemical and spectroscopic techniques. Other flavonoids that have been identified include: quercetin 3-O-glucoside and quercetin 3-O-rhamnosylglucoside (rutin).
Publication DOI: 10.4314/bcse.v11i1.21013Journal NLM ID: 101549991Publisher: Addis Ababa
Institutions: Department of Chemistry, Department of Physiology, College of Medical Science, University of Maiduguri, P.M.B. 1069, Maiduguri, Nigeria
Methods: 13C NMR, 1H NMR, FAB-MS, TLC, ESI-MS, acid hydrolysis, chemical methods, extraction
- Article ID: 11130
Hasrat JA, Pieters L, Claeys M "Adenosine-1 active ligands: Cirsimarin, a flavone glycoside from Microtea debilis" -
Journal of Natural Products 60(6) (1997) 638-641
Several plants collected through different approaches were screened on distinct receptors using ligand-binding studies as bioassay. Extracts of Microtea debilis showed high activity on adenosine A(1) receptors. Bioassay-guided fractionation using ligand-binding studies resulted in the isolation of an adenosine A(1) active ligand, cirsimarin (cirsimaritin 4'-O-glucoside). GTP did not influence the radioligand inhibition curve of cirsimarin, indicating that this compound is acting as an antagonist at the adenosine-A(1) receptors. The use of this plant against ''proteinuria'' in traditional medicine in Suriname (South America) may be explained by the adenosine A(1) antagonistic action of cirsimarin. A series of flavonoids was tested in the same assay, but they were less active. No structure-activity relationship could be observed.
NCBI PubMed ID: 9214739Publication DOI: 10.1021/np970025kJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Institutions: Department of Pharmaceutical Sciences, University of Antwerp, Universiteitsplein 1, B-2610, Antwerp, Belgium
Methods: 13C NMR, 1H NMR, FAB-MS, TLC, acid hydrolysis, biological assays, UV, extraction
- Article ID: 11148
Olea RSG, Roque NF, Bolzani VD "Acylated flavonol glycosides and terpenoids from the leaves of Alibertia sessilis" -
Journal of the Brazilian Chemical Society 8(3) (1997) 257-259
Two novel acylated flavonol glycosides, along with iridoids, triterpenes, steroids and a-tocopherolquinone, were iso lated from the leaves of Alibertia sessilis (Rubiaceae). The determination of the structures of the new compounds was based mainly on 1H- and 13C-NMR.
terpenoids, Rubiaceae, Iridoids, Alibertia sessilis, cylated flavonol glycosides, α-tocopherolquinone
Journal NLM ID: 101511356WWW link: http://www.jbcs.sbq.org.br/imagebank/pdf/v8n3a13.pdfPublisher: Sociedade Brasileira de Quimica
Institutions: Instituto de Química, Universidade de São Paulo, CP 26077, 05599-970 - SP, Brazil
Methods: 13C NMR, 1H NMR, TLC, chemical methods, extraction
- Article ID: 11161
Arot LOM, Williams LAD "A flavonol glycoside from Embelia schimperi leaves" -
Phytochemistry 44(7) (1997) 1397-1398
A new flavonol glycoside, quercetin 3-galactosyl(1→2)rhamnoside, has been isolated from the leaves of Embelia schimperi. The known compounds quercetin 3-rutinoside, quercetin 3-rhamnoside, quercetin 3-galactoside, myricetin and quercetin were also identified from this plant.
structural elucidation, Myrsinaceae, Embelia schimperi, quercetin 3-galactosyl(1→2)rhamnoside
Publication DOI: 10.1016/S0031-9422(96)00706-6Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Kenya Forestry Research Institute, Non-Timber Forest Products Research, Nairobi, Kenya
Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, sugar analysis, TLC, acid hydrolysis, chemical methods, UV, extraction, RP
- Article ID: 11524
Stassi V, Verykokidou E, Loukis A, Harvala C "Polyphenolic compounds from the leaves of Juniperus oxycedrus L. subsp. macrocarpa (Sm.) ball" -
Pharmaceutica Acta Helvetiae 72(5) (1998) 311-312
glycoside, extract, rutin, Juniperus oxycedrus
Publication DOI: 10.1016/S0031-6865(97)00037-XJournal NLM ID: 0401134Publisher: Schweizerische Apotheker-Verein
Institutions: Institute of Pharmaceutical Research and Technology, Pallini Attikis, Greece, Division of Pharmacognosy, Faculty of Pharmacy, Athens, Greece
Methods: 1H NMR, TLC, acid hydrolysis, UV, extraction, CC
- Article ID: 11613
Matławska I, Sikorska M "Flavonoid compounds in the flowers of Urena lobata L. (Malvaceae)" -
Acta Poloniae Pharmaceutica 56(1) (1999) 69-71
The following flavonoid compounds have been isolated and identified from flowers of Urena lobata L.: kaempferol 3-O-(6-O-trans-p-coumaroyl)-β-glucoside (tiliroside), dihydrokaempferol 4'-O-β-glucopyranoside, kaempferol and quercetin 3-O-β-glucosides and 3-O-β-rutinosides also luteolin 4'-O-β-glucopyranoside. Their structures were established by conventional (acid, enzymatic and alkaline hydrolysis) and spectral analysis (UV, 1H NMR, 13C NMR). Chromatographical investigations indicated the presence of quercetin, kaempferol and kaempferol 7-O-glucoside.
flavonoid, quercetin, kaempferol, luteolin, Malvaceae, Urena lobata L., dihydrokaempferol glycosides, tiliroside
Journal NLM ID: 2985167RWWW link: https://ptfarm.pl/pub/File/Acta_Poloniae/1999/1/069.pdfPublisher: Polski Towarzystwo Farmaceutyczne
Institutions: Department of Pharmacognosy, Karol Marcinkowski University of Medical Sciences in Poznań 10 Sieroca Str., 61-771 Poznań, Poland
Methods: 13C NMR, 1H NMR, TLC, enzymatic hydrolysis, alkaline hydrolysis, UV, PC, HCl hydrolysis
- Article ID: 11799
Felser C, Schimmer O "Flavonoid glycosides from Alchemilla speciosa" -
Planta Medica 65(7) (1999) 668-670
The new flavonol glycosides quercetin 3-O-β-(2-O-α-L-rhamnopyranosyl)-glucopyranoside uronic acid and kaempferol 3-O-β-(2-O-α-L-rhamnopyranosyl)-glucopyranoside uronic acid were isolated from the leaves of Alchemilla speciosa Buser together with 13 known flavonol and flavone glycosides and (+)-catechin. The structures were determined by spectroscopic methods.
flavonol glycosides, Alchemilla speciosa, spectroscopic methods
NCBI PubMed ID: 17260291Publication DOI: 10.1055/s-2006-960845Journal NLM ID: 0066751Publisher: George Thieme
Institutions: Institut für Botanik und Pharmazeutische Biologie, Lehrstuhl Pharmazeutische Biologie, Universität Erlangen-Nürnberg, Erlangen, Germany
Methods: 13C NMR, 1H NMR, methylation, TLC, HPLC, UV, acetylation, HCl hydrolysis
- Article ID: 11951
Beck MA, Häberlein H "Flavonol glycosides from Eschscholtzia californica" -
Phytochemistry 50(2) (1999) 329-332
The aqueous EtOH extract of aerial parts of Eschscholtzia californica Cham. yielded six flavonol 3-O-glycosides including two new compounds: quercetin 3-O-[α-rhamnopyranosyl-(1-4)-α-rhamnopyranosyl-(1-6)-β-glucopyranoside] and isorhamnetin 3-O-[α-rhamnopyranosyl-(1-4)-α-rhamnopyranosyl-(1-6)-β-glucopyranoside]. Their structures were established on the basis of spectroscopic studies.
Eschscholtzia californica, Papaveraceae, flavonol 3-O-glycosides
NCBI PubMed ID: 9933948Publication DOI: 10.1016/S0031-9422(98)00503-2Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: Häberlein H
Institutions: Department of Pharmaceutical Biology, Philipps University, Marburg, Germany
Methods: 13C NMR, 1H NMR, TLC, ESI-MS, acid hydrolysis, HPLC, UV
- Article ID: 11977
Adesina SK, Idowu O, Ogundaini AO, Oladimeji H, Olugbade TA, Onawunmi GO, Païs M "Antimicrobial constituents of the leaves of Acalypha wilkesiana and Acalypha hispida" -
Phytotherapy Research 14(5) (2000) 371-374
An activity directed fractionation of a 50% aqueous ethanol extract of A. wilkesiana and A. hispida leaves resulted in the isolation of gallic acid, corilagin and geraniin as the compounds responsible for the observed antimicrobial activity. Quercetin 3-O-rutinoside and kaempferol 3-O-rutinoside were also isolated from the inactive fraction of A. hispida. The structures were established by permethylation, 2D - NMR ((1)H and (13)C) and MS data.
antimicrobial, Acalypha wilkesiana, Acalypha hispida, corilagin, geraniin
NCBI PubMed ID: 10925407Publication DOI: 10.1002/1099-1573(200008)14:5<371::aid-ptr625>3.0.co;2-fJournal NLM ID: 8904486Publisher: Chichester: Wiley
Institutions: Faculty of Pharmacy, Obafemi Awolowo University, Ile-Ife, Nigeria, Institute de Chimie des Substances Naturelles, Centre National de la Recherche Scientific, Gif sur Yvette, France
Methods: 13C NMR, 1H NMR, methylation, TLC, ESI-MS, biological assays, extraction, optical rotation measurement, CC, evaporation, antimicrobial assay
- Article ID: 11993
Alluis B, Pérol N, El hajji H, Dangles O "Water-soluble flavonol (= 3-hydroxy-2-phenyl-4H-1-benzopyran-4-one) derivatives: Chemical synthesis, colouring, and antioxidant properties" -
Helvetica Chimica Acta 83(2) (2000) 428-443
Water-soluble derivatives of rutin, a very common glycoside of quercetin (=3,3′,4′,5,7-pentahydroxyflavone=2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one) and a potent plant antioxidant from the flavonol family, were synthesized by simple chemical procedures aimed at introducing carboxy or sulfo groups at the sugar moiety (Scheme 1). Such derivatives form stable molecular complexes with malvin, a polyphenolic pigment from the anthocyanin family, and thereby prove to be very effective in the enhancement (hyperchromism) and variation (bathochromism) of natural colours. The H2O-solubilizing carboxylate and sulfate groups are shown to deeply modify the enthalpy-entropy balance of the pigment-flavonol complexation (copigmentation). A molecular interpretation of the complexation-induced bathochromic shift in the pigment VIS band is proposed. Finally, the H2O-soluble rutin derivatives are shown to retain the high antioxidant ability of rutin as evidenced by their efficient trapping of the coloured radical DPPH (=2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl).
chemical synthesis, derivatives, rutin, malvin, natural pigments
Publication DOI: 10.1002/(SICI)1522-2675(20000216)83:2<428::AID-HLCA428>3.0.CO;2-JJournal NLM ID: 2985094RPublisher: Verlag Helvetica Chimica Acta
Correspondence: dangles@univ-lyon1.fr
Institutions: Université Claude Bernard-Lyon I, UMR-CNRS 5078, Laboratoire des Polyphénols, Villeurbanne, France, Université Cadi Ayyad, Faculté des Sciences et Techniques-Guéliz, Marrakech, Maroc
Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, TLC, ESI-MS, chemical synthesis, UV, acetylation, fluorescence spectroscopy, CC, antioxidant activities, spectrophotometry, derivatization
- Article ID: 12005
Ashida H, Fukuda I, Yamashita T, Kanazawa K "Flavones and flavonols at dietary levels inhibit a transformation of aryl hydrocarbon receptor induced by dioxin" -
FEBS Letters 476(3) (2000) 213-217
Dioxins invade the body mainly through the diet, and produce toxicity through the transformation of aryl hydrocarbon receptor (AhR). An inhibitor of the transformation should therefore protect against the toxicity and ideally be part of the diet. We examined flavonoids ubiquitously expressed in plant foods as one of the best candidates, and found that the subclasses flavones and flavonols suppressed antagonistically the transformation of AhR induced by 1 nM of 2,3,7,8-tetrachlorodibenzo-p-dioxin, without exhibiting agonistic effects that transform AhR. The antagonistic IC(50) values ranged from 0.14 to 10 μM, close to the physiological levels in human.
flavonoid, cancer prevention, dioxin antagonist, aryl hydrocarbon receptor, transformation inhibitor, dietary phytochemical
NCBI PubMed ID: 10913616Publication DOI: 10.1016/s0014-5793(00)01730-0Journal NLM ID: 0155157Publisher: Elsevier
Correspondence: Kanazawa K
Institutions: Laboratory of Food and Nutritional Chemistry, Faculty of Agriculture, Kobe University, Kobe, Japan
Methods: DNA techniques, biological assays, radiolabeling, centrifugation, autoradiography
- Article ID: 12009
Awad MA, de Jager A "Flavonoid and chlorogenic acid concentrations in skin of ‘Jonagold’ and ‘Elstar’ apples during and after regular and ultra low oxygen storage" -
Postharvest Biology and Technology 20(1) (2000) 15-24
Apples are important dietary sources of potentially healthy phenolics. In three successive seasons, the changes in concentrations of flavonoids and chlorogenic acid in the skin of two apple cultivars ‘Jonagold’ and ‘Elstar’ during and after regular (RS) and ultra low oxygen storage (ULO) at 1°C, were quantified by reversed-phase high performance liquid chromatography (RP-HPLC) with UV-VIS detector. There were no significant differences in the concentrations of flavonoids and chlorogenic acid between fruits stored under ULO and RS conditions. During storage of both ‘Jonagold’ (3, 6 and 8 months) and of ‘Elstar’ (2, 4 and 6 months), and during 1 or 2 weeks shelf life, the concentrations of cyanidin 3-galactoside and quercetin glycosides were relatively constant, while the concentrations of catechins, phloridzin and chlorogenic acid showed only minor changes. Exposing ‘Jonagold’ and ‘Elstar apples’ to white light during shelf life following storage increased the concentration of cyanidin 3-galactoside but not any of the other flavonoid classes. An explanation for this might be that the synthesis of different flavonoid classes may have different spectral sensitivity characteristics. It is concluded that flavonoids present in apples are stable and possibly not subject to net metabolic turnover during storage and shelf life.
phenolics, flavonoids, chlorogenic acid, storage condition, storage duration, quality
Publication DOI: 10.1016/S0925-5214(00)00116-2Journal NLM ID: 9884964Publisher: Amsterdam; New York: Elsevier
Correspondence: a.de.jager@fpo.agro.nl
Institutions: Fruit Research Station, Zetten, The Netherlands
Methods: UV, extraction, RP-HPLC, spectrophotometry
- Article ID: 12011
Awad MA, de Jager A, van Westing LM "Flavonoid and chlorogenic acid levels in apple fruit: characterisation of variation" -
Scientia Horticulturae 83(3-4) (2000) 249-263
Variations in flavonoid and chlorogenic acid levels within fruit, within tree, between orchards, between cultivars and among mutants were characterised and quantified in ‘Elstar’ and ‘Jonagold’ apples by reversed-phase high performance liquid chromatography (RP-HPLC). The sun-exposed skin of individual fruit had much higher cyanidin 3-galactoside (anthocyanin) and quercetin 3-glycoside levels than the shaded skin, while phloridzin, catechins and chlorogenic acid were similar in the skin of both sides. Individual flavonoid and chlorogenic acid levels were not equally distributed within the fruit. Quercetin 3-glycosides and anthocyanin were almost exclusively found in the skin. Catechins were mostly found in the skin but some were present in the flesh. Phloridzin was most abundant in the seeds, with intermediate levels in both the core area and the skin, and the lowest level in the flesh. Chlorogenic acid was mainly present in the core area and the seeds with an intermediate level in the flesh and a low level in the skin. The levels of anthocyanin, quercetin 3-glycosides and total flavonoids were highest in fruit borne in the top of the tree followed by fruit from the outer tree parts, whereas the lowest levels were found in fruit from the inner tree. Terminal fruit contained the highest levels of these compounds, including catechins, compared to lateral and spur fruit. Phloridzin and chlorogenic acid were not affected by the position of the fruit in the tree nor by the bearing wood type. There were large differences in flavonoid and chlorogenic acid levels in ‘Elstar’ fruit between two normally productive orchards differing mainly in growth vigour. ‘Jonagold’ and its mutants had considerably higher levels of flavonoid and chlorogenic acid than ‘Elstar’ and its mutants. The most blushed mutants of both cultivars had higher levels of anthocyanin but not of flavonoids or chlorogenic acid compared to the standard cultivar and to the less blushed mutants. The most blushed mutants had a higher number of red cells per cell layer and more cell layers containing red cells than the standard cultivar and the less blushed mutants.
variation, flavonoids, apple, anthocyanin, chlorogenic acid
Publication DOI: 10.1016/S0304-4238(99)00124-7Journal NLM ID: 9882883Publisher: Amsterdam, International Society for Horticultural Science
Correspondence: a.de.jager@fpo.agro.nl
Institutions: Fruit Research Station, Randwijk, The Netherlands
Methods: UV, extraction, microscopy, RP-HPLC, spectrophotometry, sonication
- Article ID: 12020
Basile A, Sorbo S, Giordano S, Ricciardi L, Ferrara S, Montesano D, Castaldo Cobianchi R, Vuotto ML, Ferrara L "Antibacterial and allelopathic activity of extract from Castanea sativa leaves" -
Fitoterapia 71 (2000) ID S110-S116
Following the extraction of Castanea sativa with an aqueous solution of sulfuric acid (pH 3.0), the ethyl acetate soluble fraction was tested for its antibacterial and allelopathic activity. The extract was shown to have pronounced antibacterial effects against seven of the eight strains of Gram-positive and Gram-negative bacteria used (MIC in the range of 64-256 μg/ml and MBC in the range of 256-512 μg/ml). The active fraction was analyzed by TLC and HPLC showing the presence of rutin, hesperidin, quercetin, apigenin, morin, naringin, galangin and kaempferol. Standards of the identified flavonoids were tested against the same bacterial strains. The highest activity was shown by quercetin, rutin and apigenin. The allelopathic effect was tested against Raphanus sativus seed germination. The extract, quercetin, rutin and apigenin caused a decrease in the percentage of seed germination and root and epicotyl growth.
antibacterial activity, flavonoids, Castanea sativa, allelopathic activity
NCBI PubMed ID: 10930721Publication DOI: 10.1016/s0367-326x(00)00185-4Journal NLM ID: 16930290RPublisher: Elsevier
Correspondence: adbasile@unina.it
Institutions: Dipartimento di Biologia Vegetale, Università degli Studi di Napoli 'Federico II', Naples, Italy, Istituto di Patologia Generale ed Oncologia, Facoltà di Medicina e Chirurgia, Seconda Università degli Studi, Naples, Italy, Dipartimento di Chimica Farmaceutica, Università 'Federico II', Naples, Italy
Methods: TLC, HPLC, extraction, antibacterial assay, evaporation, germination assay
- Article ID: 12040
Bilia AR, Salvini D, Mazzi G, Vincieri FF "Characterization of calendula flower, milk-thistle fruit, and passion flower tinctures by HPLC-DAD and HPLC-MS" -
Chromatographia 53 (2000) 210–215
As a part of an investigation of the content of herbal drug preparations and herbal medicinal products, we have investigated tinctures (prepared with 40:60 and 60:40 (%,v/v) ethanolwater) of calendular flower, milk-thistle fruit, and passion flower, which are, respectively, widely used for their anti-inflammatory properties, to treat hepatic injuries, and to treat tension and difficulty falling asleep. The aim of this work was to evaluate the flavonoid content, because flavonoids are the active constituents or markers of these herbal drugs, and to establish the best solvent for the extraction of the constituents. The findings reported herein both confirm the presence of several flavonoids previously identified in these herbal drugs and report the presence of others not previously described and identified here for the first time. In general the flavonol content was highest in 60% tinctures. A rapid, reversed-phase (RP) HPLC assay was developed and validated and enabled good separation of all classes of flavonoids including flavones, flavonols, flavanonols, and flavanolignans. Aglycones and mono, di, and triglycosides (bothO-andC-derivatives) of the flavonoids are also easily and satisfactorily separated. This method is thus proposed for the analysis of other herbal drugs or herbal drug preparations in which flavonoids are the active constituents or markers.
mass spectrometry, thin-layer chromatography, column liquid chromatography, flavonoids and tinctures, calendula flower, milk-thistle fruit and passion flower
Publication DOI: 10.1007/BF02491573Journal NLM ID: 0316520Publisher: Friedr. Vieweg Und Sohn Verlags Gmbh
Correspondence: ar.bilia@unifi.it
Institutions: Dipartimento di Scienze Farmaceutiche, Florence, Italy
- Article ID: 12042
Bisignano G, Sanogo R, Marino A, Aquino R, D'Angelo V, Germano MP, De Pasquale R, Pizza C "Antimicrobial activity of Mitracarpus scaber extract and isolated constituents" -
Letters in Applied Microbiology 30(2) (2000) 105-108
The antimicrobial activity of a methanol extract and isolated constituents of Mitracarpus scaber, a species used in folk medicine by West African native people, was evaluated against Staphylococcus aureus and Candida albicans strains. The mitracarpus methanol extract possesses both antibacterial and antimycotic activities (minimum inhibitory concentration-MIC 31.25 and 62.50 μg/ml, respectively). This extract was subsequently fractioned and monitored by bioassays leading to the isolation of seven compounds screened for antibacterial and antimycotic activities. Among these compounds, gallic acid and 3,4,5-trimethoxybenzoic acid inhibited the growth of Staph. aureus (MIC 3.90 and 0.97 μg/ml). 4-Methoxyacetophenone and 3,4,5-trimethoxyacetophenone effectively inhibited C. albicans (MIC 1.95 μg/ml). The other compounds (kaempferol-3-O-rutinoside, rutin and psoralen) which were also isolated showed low antibacterial and antimycotic activities (125-500 μg/ml).
Staphylococcus aureus, Candida albicans, antimicrobial activity, Mitracarpus scaber, West African medicine
NCBI PubMed ID: 10736009Publication DOI: 10.1046/j.1472-765x.2000.00692.xJournal NLM ID: 8510094Institutions: Pharmaco-Biological Department, Microbiological Section, School of Pharmacy, University of Messina, Messina, Italy, Pharmaceutical Science Department, School of Pharmacy, University of Salerno, Salerno, Italy
Methods: TLC, extraction, CC, antibacterial assay, antifungal activity test
- Article ID: 12052
Capasso A, Saturnino P, Simone FD, Aquino R "Flavonol glycosides from Aristeguietia discolor reduce morphine withdrawal in vitro" -
Phytotherapy Research 14(7) (2000) 538-540
The effects of extracts, partially purified fractions and four flavonol glycosides 1-4 from Aristeguietia discolor were investigated on the naloxone-precipitated withdrawal contraction of the acute morphine dependent guinea-pig ileum in vitro. After a 4 min in vitro exposure to morphine a strong contraction of guinea-pig isolated ileum was observed after the addition of naloxone. Both MeOH extract (50, 100 and 200 mg/mL), the partially purified fractions I, L, M and N (50, 100 and 200 mg/mL) and flavonol glycosides 1-4 (100, 50, 10 μM), injected 10 min before morphine, were capable of blocking the naloxone-induced contraction after exposure to morphine in a concentration-dependent fashion. The results of the present paper suggest that flavonol glycosides from Aristeguietia discolor may play an important role in the control of morphine withdrawal.
guinea-pig ileum, Aristeguietia discolor, morphine, naloxone
NCBI PubMed ID: 11054845Publication DOI: 10.1002/1099-1573(200011)14:7<538::aid-ptr631>3.0.co;2-1Journal NLM ID: 8904486Publisher: Chichester: Wiley
Correspondence: Capasso A
Institutions: Dipartimento di Scienze Farmaceutiche, Università di Salerno, Salerno, Italy
Methods: biological assays
- Article ID: 12053
Capasso A, Piacente S, De Tommasi N, Ragucci M, Pizza C "Constituents of Croton menthodorus and their effects on electrically induced contractions of the guinea-pig isolated ileum" -
Phytotherapy Research 14(3) (2000) 156-159
The present study examines the effects of the extracts [petroleum ether, CHCl3, CHCl3/MeOH (9:1) and MeOH], partially purified fractions and pure compounds from Croton menthodorus on the electrically induced contractions of the isolated guinea-pig ileum (ECI). The results of the experiments indicate that CHCl(3)/MeOH (9:1) and MeOH extracts, tested at concentrations of 100, 50 and 25 μg/mL, dose-dependently reduced the guinea-pig ileum contractions, whereas petroleum ether and CHCl3 extracts did not affect it. Furthermore, the partially purified fractions III-VI from the CHCl3/MeOH extract, each tested at concentrations of 100, 50 and 25 μg/mL also inhibited ECI. Finally, pure compound 1 (6, 3, 1 μM) isolated and purified from the most active fraction III significantly reduced, in a dose-dependent manner, the electrical contractions of the ileum. Compound 1 was identified by NMR and EI-MS data as the morphinandien-7-one, O-methylflavinantine.
flavonol glycosides, guinea-pig ileum, Croton menthodorus, electrically induced contractions, O-methylflavinantine
NCBI PubMed ID: 10815006Publication DOI: 10.1002/(sici)1099-1573(200005)14:3<156::aid-ptr630>3.0.co;2-vJournal NLM ID: 8904486Publisher: Chichester: Wiley
Correspondence: Capasso A
Institutions: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Salerno, Salerno, Italy
Methods: 13C NMR, 1H NMR, EI-MS, TLC, biological assays, extraction, CC, RP-HPLC
- Article ID: 12066
Chen G, Zhang H, Ye J "Determination of rutin and quercetin in plants by capillary electrophoresis with electrochemical detection" -
Analytica Chimica Acta 423(1) (2000) 69-76
A method based on capillary electrophoresis with electrochemical detection (CE-ED) was developed for the determination of daidzein, rutin and quercetin. The effects of some important factors such as the acidity and concentration of running buffer, separation voltage, injection time, and detection potential were investigated to acquire the optimum conditions. The working electrode was a 300 μm diameter carbon disc electrode positioned opposite the outlet of capillary. The three analytes could be well separated within 10 min in a 40 cm length capillary at a separation voltage of 12 kV in a 100 mmol/l borate buffer (BB, pH 9.0). The response was linear over three orders of magnitude with detection limits (S/N=3) ranged from 0.190 to 0.434 μmol/l for all compounds. This proposed method demonstrated good long-term stability and reproducibility with relative standard deviations (R.S.D.) of less than 5% for both migration time and peak current (n=7). It has been successfully applied for the determination of rutin and quercetin in Chinese traditional drug, Flos Sophorae buds and in the leaves of Ligustrum lucidum Ait. and Cinnamomum camphora (L.) Presl.
capillary electrophoresis, quercetin, rutin, daidzein, electrochemical detection
Publication DOI: 10.1016/S0003-2670(00)01099-0Journal NLM ID: 0370534Correspondence: Ye J
Institutions: Department of Chemistry, East China Normal University, Shanghai, China, Shanghai SIIC-SMU Bio-Technique Co. Ltd., Shanghai, China
Methods: extraction, capillary electrophoresis (CE), evaporation
- Article ID: 12067
Chen S-S, Gong J, Liu F-T, Mohammed U "Naturally occurring polyphenolic antioxidants modulate IgE-mediated mast cell activation" -
Immunology 100(4) (2000) 471-480
Reactive oxygen species (ROS) are known to modulate activities of a host of kinases, phosphatases and transcription factors. Rutin and chlorogenic acid (CGA) are the major polyphenolic antioxidants present in the small molecular fraction of smokeless tobacco leaf extracts, as ascertained by reverse-phase high-pressure liquid chromatography (HPLC) and mass spectrometry. Levels of intracellular ROS in resting versus antigen-immunoglobulin E (IgE)-challenged murine mast cells were measured at 510 nm by fluorescence-activated cell sorting (FACS) using carboxy-dichlorofluorescein (DCFH-DA). Enhanced ROS production was observed in IgE-sensitized mast cells following antigenic challenge. Rutin and CGA reduced ROS levels in antigen-IgE-activated mast cells. Concomitantly, they also profoundly inhibited histamine release by these activated mast cells. In contrast, rutin and CGA augmented the inducible cytokine messages, i.e. interleukin (IL)-10, IL-13, interferon-gamma (IFN-γ), IL-6 and tumour necrosis factor-alpha (TNF-α) in IgE-sensitized mast cells following antigen challenge. This study indicates that tobacco polyphenolic antioxidants that quench intracellular ROS, differentially affect two effector functions of antigen-IgE-activated mast cells. This model system may be employed to determine the molecular target of polyphenols. The potential role of these polyphenolic antioxidants on IgE-mediated allergy in vivo depends on a balance of their differential effects on mast cell activation.
Antioxidants, reactive oxygen species (ROS), rutin, chlorogenic acid
NCBI PubMed ID: 10929074Publication DOI: 10.1046/j.1365-2567.2000.00045.xJournal NLM ID: 0374672Publisher: Oxford, UK: Blackwell Scientific Publications
Institutions: Division of Allergy, La Jolla Institute for Allergy and Immunology, La Jolla, USA, Division of Immunochemistry, La Jolla Institute for Allergy and Immunology, La Jolla, USA, Department of Pathology and Microbiology, University of Nebraska Medical Center, Omaha, USA
Methods: MS, radioactivity measurement, extraction, immunological assays, RP-HPLC, dialysis, protein detection, centrifugation, measurement of cytokines, ROS measurement
- Article ID: 12075
Chevalley I, Marston A, Hostettmann K "New phenolic radical scavengers from Saxifraga cuneifolia" -
Pharmaceutical Biology 38(3) (2000) 222–228
Thirteen compounds have been isolated from the methanol extract of Saxifraga cuneifolia L. (Saxifragaceae) whole plant. These were identified as five new compounds, (E)-5-O-β-D-glucopyranosyl-stilbene-3,3', 4,5'-tetraol, (E)-4-O-β-D-glucopyranosyl-5-methoxy-stilbene-3,3',5'-triol, 4-[4'-O-(6''-O-galloyl-β-D-glucopyranosyl)-3'-hydroxyphenyl]butan-2-one, 3-O-(6''-O-galloyl-β-D-glucopyranosyl)-epigallocatechin and 3-O-β-D-glucopyranosyl-epigallocatechin, together with the known compounds 4-[4'-O-β-D-glucopyranosyl-3'-hydroxyphenyl]-butan-2-one, (R)-rhododendrin, 1-O-galloyl-β-D-glucose, catechin, 3-O-galloyl-epigallocatechin, gallocatechin, clitorin and rutin, by chemical and spectroscopic methods. Their free radical scavenging properties are also described.
flavonoid glycosides, free radical scavengers, Saxifragaceae, catechin derivatives, phenylbutan-2-one glycosides, (R)-rhododendrin, Saxifraga cuneifolia, stilbene glycosides
NCBI PubMed ID: 21214466Publication DOI: 10.1076/1388-0209(200007)3831-SFT222Journal NLM ID: 9812552Publisher: Lisse, the Netherlands: Swets & Zeitlinger
Correspondence: kurt.hostettmann@ipp.unil.ch
Institutions: Institut de Pharmacognosie et Phytochimie, Université de Lausanne, Lausanne, Switzerland
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS/MS, HPLC, alkaline hydrolysis, UV, enzymatic digestion, extraction, optical rotation measurement, CC, melting point determination, radical reduction assay
- Article ID: 12099
Coulombe Jr. RA "Natural toxins and chemopreventives in plants" -
Book: Food Toxicology (2000) Chapter 6, 137-161
Our food contains, in addition to the many well-known major (protein, fat, carbohydrate, and fiber) and minor (vitamins, minerals, and nonessential compounds) nutrients, thousands of naturally present toxic plant compounds. Some are known or strongly suspected to cause cancer in laboratory animals and, thus, may be potentially carcinogenic in people. Many of these compounds are commonly termed "nature's pesticides" because they are often toxic to predators, such as insects and animals, thereby conferring a competitive advantage to the plant that produces them. Other natural toxins in plants have no known role. Although these chemicals are in every meal we eat, they have received little attention compared to that given to minute residues of synthetic chemicals such as PCBs and pesticides. Our food contains significantly greater amounts of natural plant toxins and carcinogens than the synthetic kind, and our bodies aren't able to distinguish between the two. Still, while popular notion remains that "natural is good," it is clear that natural toxins pose a far greater health risk than that posed by synthetic chemicals in our foods.
Publication DOI: 10.1201/9781420038316.ch6Publisher: CRC Press, Inc.
Editors: Helferich W, Winter CK
Institutions: Utah State University, Logan, USA
- Article ID: 12105
Dangles O, Dufour C, Fargeix G "Inhibition of lipid peroxidation by quercetin and quercetin derivatives: antioxidant and prooxidant effects" -
Journal of the Chemical Society, Perkin Transactions 2 2(6) (2000) 1215–1222
Flavonoids (polyphenols) are an important class of dietary antioxidants largely distributed in plants. In spite of their very fast reaction with lipid peroxyl radicals, flavonoids are relatively modest inhibitors of lipid peroxidation in solution. In addition, the absence of lag phase and the strong dependence of the antioxidant efficiency (the ratio of the rate constant of chain break to the rate constant of chain propagation) on the antioxidant concentration both point to a nonclassic behaviour. The inhibition of linoleic acid peroxidation by quercetin (3,3′,4′,5,7-pentahydroxyflavone) and its 3-O-glycoside rutin (two ubiquitous dietary flavonoids and potent antioxidants) has been investigated by UV–visible spectroscopy in pH 7.4 micellar solutions of SDS at 37 °C. The chain-breaking antioxidant α-tocopherol and two synthetic amphiphilic quercetin ethers are also considered for comparison purposes. From the general mathematical treatment developed in this work, flavonoids appear as strong chain-breaking antioxidants whose overall antiperoxidizing activity is, however, strongly restricted by the chain-initiating activity of the flavonoid radicals formed during inhibition (prooxidant effect).
Antioxidant activity, quercetin, lipid peroxidation, rutin
Publication DOI: 10.1039/A910183GJournal NLM ID: 7505599Publisher: Chemical Society
Correspondence: dangles @univ-lyon1.fr
Institutions: Université Claude Bernard-Lyon I, UMR-CNRS 5078, Villeurbanne, France, Institut National de la Recherche Agronomique, Unité de Recherche Biopolymères et Arômes, Montpellier, France
Methods: 13C NMR, 1H NMR, FAB-MS, inhibition studies, TLC, CC, antioxidant activities, HMBC, evaporation, alkylation, spectrometry
- Article ID: 12119
Degenhardt A, Engelhardt UH, Lakenbrink C, Winterhalter P "Preparative separation of polyphenols from tea by high-speed countercurrent chromatography" -
Journal of Agricultural and Food Chemistry 48(8) (2000) 3425-3430
High-speed countercurrent chromatography (HSCCC) was applied to the separation of polyphenols from tea leaves (Camellia sinensis L.). The capability of HSCCC to isolate pure tea polyphenols from complex mixtures on a preparative scale was demonstrated for catechins, flavonol glycosides, proanthocyanidins, and strictinin from green and black tea. The purity and identity of isolated compounds was confirmed by (1)H NMR and HPLC-ESI-MS/MS. Gram quantities of polyphenols from tea can be isolated with the procedure described.
high-speed countercurrent chromatography, flavonol glycosides, Camellia sinensis, polyphenols, catechins, green tea, black tea, HPLC-ESI-MS, proanthocyanidins, strictinin
NCBI PubMed ID: 10956128Publication DOI: 10.1021/jf0000833Journal NLM ID: 0374755Publisher: American Chemical Society
Institutions: Institut für Lebensmittelchemie, Technische Universität Braunschweig, Braunschweig, Germany
Methods: 1H NMR, ESI-MS/MS, extraction, HSCCC, HPLC-ESI-MS/MS
- Article ID: 12143
Du X-M, Sun N-Y, Shoyama Y "Flavonoids from Goodyera schlechtendaliana" -
Phytochemistry 53(8) (2000) 997-1000
A flavonol glycoside, 3-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxi]-5,7-dihydroxy-8-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-2-(3,4-dihydroxypheny)-4H-1-benzopyran-4-one, trivially named goodyerin, was isolated from the whole plant of Goodyera schlechtendaliana, along with three known flavonoids, rutin, kaempferol-3-O-rutinoside and isorhamnetin-3-O-rutinoside. The structures were established by spectroscopic analysis.
flavonoids, Orchidaceae, Goodyera schlechtendaliana, goodyerin
NCBI PubMed ID: 10820819Publication DOI: 10.1016/s0031-9422(00)00027-3Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: shoyama@shoyaku.pharm.kyushu-u.ac.jp
Institutions: Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan, Seiwa Pharmaceutical Ltd., Tokyo, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, TLC, acid hydrolysis, GC, UV, extraction, optical rotation measurement, CC, RP-HPLC, melting point determination, derivatization, evaporation, HR-FAB-MS
- Article ID: 12149
DuPont MS, Mondin Z, Williamson G, Price KR "Effect of variety, processing, and storage on the flavonoid glycoside content and composition of lettuce and endive" -
Journal of Agricultural and Food Chemistry 48(9) (2000) 3957-3964
Eight varieties of lettuce (Lactuca sativum) and three varieties of endive (Cichorium endivia) were analyzed for flavonoid composition and content. Total flavonoid contents, expressed as units of aglycon for fresh material, were in the ranges of 0.3-229 μg/g for lettuce and 44-248 μg/g for endive. Five quercetin conjugates [quercetin 3-O-galactoside, quercetin 3-O-glucoside, quercetin 3-O-glucuronide, quercetin 3-O-(6-O-malonyl)glucoside, and quercetin 3-O-rhamnoside] and luteolin 7-O-glucuronide were measured in the green-leafed lettuce and an additional two cyanidin conjugates [cyanidin 3-O-glucoside and cyanidin 3-O-[(6-O-malonyl)glucoside]] in the red-leafed varieties. Three kaempferol conjugates [kaempferol 3-O-glucoside, kaempferol 3-O-glucuronide, and kaempferol 3-O-[6-O-malonyl)glucoside]] were measured in each of the endive varieties. The presence and identity of kaempferol 3-O-(6-O-malonyl)glucoside in endive was shown for the first time. Shredding of lettuce leaf followed by exposure to light produced significant losses of the flavonoid moiety in the green oak leaf (94%), red oak leaf (43%), iceberg (36%), green batavia (25%), lollo biondo (24%), and lollo rosso (6%) samples, whereas cos and green salad bowl samples did not show an overall loss. Shredding of endive also produced loss of the flavonoid moiety in escarole (32%), fine frisee (13%), and coarse frisee (8%). Significant demalonation was observed for both the quercetin and cyanidin glucosides in lettuce, whereas a similar degradation of the kaempferol analogue was found in endive tissue. Storage of whole heads of both lettuce and endive in the dark at 1 degrees C and 98% humidity for 7 days resulted in losses of total flavonol glycosides in the range of 7-46%. The identification of the amounts, position of substitution, and nature of the sugars is important for understanding the potential bioavailability and biological activities of flavonoids in salads.
HPLC, lettuce, flavonoid, endive, flavonoid conjugates
NCBI PubMed ID: 10995297Publication DOI: 10.1021/jf0002387Journal NLM ID: 0374755Publisher: American Chemical Society
Institutions: Diet, Health and Consumer Science Division, Institute of Food Research, Norwich Research Park, Norwich, UK
Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, HPLC, enzymatic digestion, extraction, CC, evaporation, APCI-MS
- Article ID: 12155
El-Mousallamy AM, Hussein SA, Merfort I, Nawwar MA "Unusual phenolic glycosides from Cotoneaster orbicularis" -
Phytochemistry 53(6) (2000) 699-704
The whole plant of Cotoneaster orbicularis contains the novel di-C-glycosylflavone, 4",4"'-di-O-β-glucopyranosyl-vicenin II, or 6,8-di-C-β-Cellobiosylapigenin, as well as the hitherto unknown natural phenolic glucoside, gentisic acid 2-O-β-glucopyranoside, or orbicularin. Further phenolics are protocatechuic, anisic, caffeic, p-coumaric acids, catechin, epicatechin, 2"-O-α-rhamnopyranosylvitexin, vitexin, rutin, isoquercetrin, hyperin and naringenin. All structures were determined by routine methods of analysis and confirmed mostly by 1H- and 13C-NMR.
NMR, ESI-MS, 6, rosaceae, whole plant, Cotoneaster orbicularis, C-glycosylЇavones, 8-di-C-cellobiosylapigenin, phenolic acid-O-glucoside, gentisic acid, 2-O-glucopyranoside, orbicularin
NCBI PubMed ID: 10746883Publication DOI: 10.1016/s0031-9422(99)00598-1Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: nawwar@worldnet.com.eg
Institutions: National Research Centre, Cairo, Egypt, Department of Chemistry, Zagazig University, Zagazig, Egypt, Institut Fur Pharmazeutische Biologie, Albert-Ludwigs Universitat, Freiburg, Germany, National Research Centre, Department of Phytochemistry, Pharmacutical Sciences Division, Cairo, Egypt
Methods: 13C NMR, 1H NMR, EI-MS, ESI-MS, acid hydrolysis, paper chromatography, UV, extraction, CC, precipitation, evaporation
- Article ID: 12159
Erlund I, Kosonen T, Alfthan G, Mäenpää J, Perttunen K, Kenraali J, Parantainen J, Aro A "Pharmacokinetics of quercetin from quercetin aglycone and rutin in healthy volunteers" -
European Journal of Clinical Pharmacology 56(8) (2000) 545-553
Quercetin is a flavonoid with a wide range of biological activities. It mainly occurs in plants as glycosides, such as rutin (quercetin rutinoside) in tea. Quercetin and rutin are used in many countries as vasoprotectants and are ingredients of numerous multivitamin preparations and herbal remedies. The primary objective was to characterise and compare the absorption and the pharmacokinetics of quercetin from quercetin aglycone and rutin. A secondary objective was to investigate which forms of quercetin are present in plasma. In this double blind, diet-controlled, two-period cross-over study, 16 healthy volunteers received three different doses of quercetin and rutin orally. The doses corresponded to 8 mg, 20 mg and 50 mg quercetin aglycone. Blood samples were obtained between 0 h and 32 h post-dose. The overall kinetic behaviour of quercetin differed remarkably after ingestion of quercetin aglycone or rutin. The mean area under the plasma concentration-time curve from 0 h to 32 h [AUC(0-32)] and maximum plasma concentration (Cmax) values of the two treatments were similar. However, time to reach Cmax (tmax) was significantly shorter after the quercetin aglycone treatment than after the rutin treatment (1.9, 2.7 and 4.8 versus 6.5, 7.4 and 7.5 h, for doses 1, 2 and 3, respectively). Also, the absorption of quercetin from quercetin aglycone was predictable and inter-individual variation was small. In contrast, after ingestion of rutin, inter-individual variations in AUC(0-32) and Cmax values were considerable and seemed to be associated with gender and use of oral contraceptives. Quercetin and rutin were found in plasma as glucuronides and/or sulfates of quercetin and as unconjugated quercetin aglycone, but no rutin was detected. In clinical trials, studying the effects of quercetin from rutin, bioavailability must be taken into consideration and plasma quercetin concentrations monitored. Whether our results apply to other glycosidic drugs as well, especially other rutosides, should be investigated.
quercetin, rutin, flavonoids
NCBI PubMed ID: 11151743Publication DOI: 10.1007/s002280000197Journal NLM ID: 1256165Publisher: Berlin, New York, Springer
Correspondence: iris.erlund@ktl.fi
Institutions: Department of Nutrition, National Public Health Institute (KTL), Helsinki, Finland, Clinical Research, Leiras Oy, Helsinki, Finland
Methods: enzymatic hydrolysis, biological assays, HPLC, CC, centrifugation
- Article ID: 12162
Escarpa A, González MC "Identification and quantitation of phenolics from green beans by high-performance liquid chromatography" -
Chromatographia 52 (2000) 33–38
High-performance liquid chromatography with diode-array detection has been used for the separation and quantitation of phenolics from fresh and processed green beans. Whole beans, pods and seeds of green beans were studied separately. Chromatographic profiles from pods were more complex than those found in seeds. Flavonol glycosides were confined to quercetin and kaempferol classes and they were typical of external parts of the fruit. Flavan-3-ols monomers ((+) catechin and (−) epicatechin) as well as procyanidins structures were identified in pods and seeds. Chromatographic profiles from processed beans revealed a polyphenolic composition similar to those found in pod fresh green beans. The chromatographic method was carefully validated in regard to precision and accuracy. High reproducibility of peak area (RSD<3%) and calibration slopes (RSD<4%) was obtained. Recoveries between 94–104% revealed good accuracy for the overall method. Application to quantitative determination in a representative number of samples allowed good knowledge of the phenolic composition of green beans (Phaseolus vulgaris v.vulgaris).
phenolics, column liquid chromatography, green beans, identification and quantitation
Publication DOI: 10.1007/BF02490789Journal NLM ID: 0316520Publisher: Friedr. Vieweg Und Sohn Verlags Gmbh
Institutions: Departamento de Química Analítica, Facultad de Ciencias, Universidad de Alcalá, Madrid, Spain
Methods: acid hydrolysis, HPLC, UV, extraction, CC, sonication
- Article ID: 12179
Friedman M, Jürgens HS "Effect of pH on the stability of plant phenolic compounds" -
Journal of Agricultural and Food Chemistry 48(6) (2000) 2101-2110
It is not uncommon to treat plant-derived foods and feeds with alkali. Such exposure to high pH is being used to recover proteins from cereals and legumes, to induce the formation of fiber-forming meat analogue vegetable protein, for preparing peeled fruits and vegetables, and for destroying microorganisms. In addition to their profound effects on functional and nutritional properties in such foods, such treatments may also cause other side reactions, including the destruction of natural polyphenolic compounds. Because plants contain a large number of structurally different antioxidant, anticarcinogenic, and antimicrobial polyphenolic compounds, it is of interest to know whether such compounds are stable to heat and to high pH. In this model study, the stability of the following natural polyphenols to pH in the range 3-11 was studied with the aid of ultraviolet spectroscopy: caffeic acid, (-)-catechin, chlorogenic acid, ferulic acid, gallic acid, (-)-epigallocatechin, rutin, and the nonphenolic compound trans-cinnamic acid. This study demonstrates that caffeic, chlorogenic, and gallic acids are not stable to high pH and that the pH- and time-dependent spectral transformations are not reversible. By contrast, chlorogenic acid is stable to acid pH, to heat, and to storage when added to apple juice. (-)-Catechin, (-)-epigallocatechin, ferulic acid, rutin, and trans-cinnamic acid resisted major pH-induced degradation. The results are rationalized in terms of relative resonance stabilization of phenoxide ions and quinone oxidation intermediates. The possible significance of these findings to food chemistry and microbiology is discussed.
plant phenols, cinnamic acid, gallic acid, rutin, ferulic acid, caffeic acid, chlorogenic acid, catechin, epigallocatechin, pH stability, ultraviolet spectra
NCBI PubMed ID: 10888506Publication DOI: 10.1021/jf990489jJournal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: mfried@pw.usda.gov
Institutions: Western Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, Albany, CA, USA
Methods: UV, spectrophotometry
- Article ID: 12182
Fukumoto LR, Mazza G "Assessing antioxidant and prooxidant activities of phenolic compounds" -
Journal of Agricultural and Food Chemistry 48(8) (2000) 3597-3604
Methods for determining primary antioxidant activity were evaluated. A beta-carotene bleaching method and a free radical method using 2, 2-diphenyl-1-picrylhydrazyl (DPPH(*)) were modified to rapidly test samples for potential antioxidant activity. Malonaldehyde production in a linoleic acid emulsion system assayed by an HPLC method was also used to determine antioxidant and prooxidant activities initiated by a metal catalyst (Cu(2+)). All methods were used to assess activity of selected phenolic compounds including several anthocyanidins/anthocyanins and selected berry extracts. Most phenolic compounds had prooxidant activity at low concentrations, unlike synthetic antioxidants (BHA and BHT). Compounds with similar structures exhibited comparable trends in antioxidant activity. Antioxidant activity usually increased with an increase in the number of hydroxyl groups and a decrease in glycosylation. The antioxidant activity of many phenolic compounds and extracts was comparable to those of synthetic antioxidants using the beta-carotene bleaching and HPLC methods.
Antioxidant activity, phenolics, flavonoids, anthocyanins, prooxidant activity, berry extracts
NCBI PubMed ID: 10956156Publication DOI: 10.1021/jf000220wJournal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: Mazzag@em.agr.ca
Institutions: Food Research Program, Pacific Agri-Food Research Centre, Agriculture and Agri-Food Canada, Summerland, Canada
Methods: HPLC, colorimetry, extraction, oxidation, antioxidant activities, evaporation
- Article ID: 12242
Hollman PCH, Arts ICW "Flavonols, flavones and flavanols – nature, occurrence and dietary burden" -
Journal of the Science of Food and Agriculture 80(7) (2000) 1081-1093
Total flavonol and flavone contents of foods have been determined with validated state-of-the-art methods. Quercetin dominates, and flavonol levels found in vegetables and fruits are below 10 mg kg−1. However, high concentrations are found in onions (300 mg/kg), kale (450 mg/kg), broccoli (100 mg/kg), beans (50 mg/kg), apples (50 mg/kg), blackcurrants (40 mg/kg), and tea (30 mg/l). The dietary intake of flavonols varies 10-fold between countries (6–60 mg/day). Flavones are of minor importance in the diet. Tea, wine and fruits are the most important sources of flavanols, but there are gaps in our knowledge on flavanol levels of many foods. The absorption of dietary quercetin glycosides in humans ranges from 20 to 50%. The sugar moiety is an important determinant of the bioavailability of flavonols. The presence of a glucose moiety significantly enhances absorption. The extent of absorption of flavanols in humans seems similar to that of flavonols but has been little studied. Flavonols and flavanols are extensively metabolised, as only 1–2% of them are excreted with an intact flavonoid backbone. Hepatic biotransformations include glucuronidation and sulphatation of the phenolic hydroxyls and O-methylation of catechol groups. Bacteria of the colon cleave the C-ring of the flavonoid nucleus to phenolic acids which are subsequently absorbed. Apart from conjugates, virtually no metabolites have been characterised in humans. Absorption of flavanols is rather fast, with times to reach peak values between 0.5 and 4 h. Flavanols are rapidly excreted, with elimination half-lives of 1–6 h. Quercetin glycosides show rapid to slow absorption; peak values are reached between < 0.5 and 9 h. The type of glycoside determines the rate of absorption. Excretion of quercetin glycosides is slow: elimination half-lives are 24 h, independent of the type of glycoside. Analytical data for flavanols in foods are needed. Tea, as an important dietary source, has to be studied. Research on the bioavailability of flavonols and flavanols has to be expanded. Attention is needed for the identification and quantification of their metabolites in body fluids.
glycosides, bioavailability, flavones, flavonols, catechins, flavanols, food contents, dietary intake, absorption metabolism, phenolic acids
Publication DOI: 10.1002/(SICI)1097-0010(20000515)80:7<1081::AID-JSFA566>3.0.CO;2-GJournal NLM ID: 0376334Publisher: Chichester, West Sussex: John Wiley And Sons Ltd
Institutions: National Institute of Public Health and the Environment, Bilthoven, The Netherlands, State Institute for Quality Control of Agricultural Products (RIKILT), Wageningen, The Netherlands
- Article ID: 12269
Kawanishi K, Farnsworth NR "Current status of the chemistry and synthesis of natural antimalarial compounds and natural substances used to alleviate symptoms of diabetes (aldose reductase and α-glucosidase inhibitors)" -
Book: Studies in Natural Products Chemistry (series: Bioactive Natural Products) (2000) Vol. 22, Chapter C, 145-192
Atropine, camptothecin, cocaine, digitoxin, digoxin, morphine, pilocarpine, quinine, taxol, vinblastine and vincristine, among others, are important drugs obtained from higher plants and are used clinically. They have also served as lead compounds for the synthesis and modification of more effective and safer drugs, in many cases. In this chapter, drugs used as antimalarial compounds and for the complications of diabetes (aldose reductase and α-glucosidase inhibitors) will be discussed. Natural product chemists have isolated as little as 1.0 mg of pure compounds from natural sources and have been able to determine their structures using high resolution instrumental techniques. Organic chemists have synthesized thousands of compounds to produce one new drug on the basis of natural product leads, and pharmacologists and biochemists have tested their biological activity. Recently chemists and pharmacologists have worked together to develop techniques for studying structure-activity relationships using computer graphics and have designed new drugs. Biochemists, molecular biologists and pharmacologists have identified many receptors on which drugs act. Thus, mechanisms of drug action at the molecular level are being identified. From the accumulation of these results structure-activity relationships will lead to the preparation of thousands of useful compounds. We must produce drugs in these ways, because we cannot rely on solely on the limited amount of active compounds produced naturally in plants, in many cases, for a number of reasons. However we need to employ plant extracts themselves, because there are millions of people who cannot buy expensive synthetic drugs in the world and these extracts are widely used by them.
Publication DOI: 10.1016/S1572-5995(00)80025-3Publisher: New York: Elsevier
Editors: Atta-ur-Rahman
Institutions: Kobe Pharmaceutical University, Kobe, Japan, Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA
- Article ID: 12284
Kim SH, Kang KW, Kim KW, Kim ND "Procyanidins in crataegus extract evoke endothelium-dependent vasorelaxation in rat aorta" -
Life Sciences 67(2) (2000) 121-131
The extract of Crataegus, a mixture of flavonoids and procyanidins extracted from hawthorn, Crataegus oxyacantha, L. and C. monogyna Jacq., relaxed vascular tone or increased production of cyclic GMP in the rat aorta, but flavonoid components of Crataegus extract, hyperoside, rutin and vitexin, did not affect the vascular tone. The aim of the present study was to characterize the endothelium-dependent relaxation elicited by procyanidins fractionated from Crataegus extract in isolated rat aorta. Procyanidins caused endothelium-dependent relaxation which was associated with the production of cyclic GMP. Both responses to these procyanidins were inhibited by methylene blue or N(G)-nitro-L-arginine, but not by indomethacin. Relaxation in response to procyanidins was not affected by atropine, diphenhydramine, [D-Pro2,D-Trp7,9]substance P, propranolol, nifedipine, verapamil and glibenclamide, but were markedly reduced by tetraethylammonium. These findings showed that procyanidins in Crataegus extract may be responsible for the endothelium-dependent nitric oxide-mediated relaxation in isolated rat aorta, possibly via activation of tetraethylammonium-sensitive K+ channels.
nitric oxide, procyanidins, aorta, vascular relaxation, cyclic GMP, K+ channels
NCBI PubMed ID: 10901280Publication DOI: 10.1016/s0024-3205(00)00608-1Journal NLM ID: 0375521Publisher: Amsterdam: Elsevier
Institutions: College of Pharmacy, Seoul National University, Seoul, South Korea, Dong-A Pharmaceutical Company Ltd., Kyunggi-Do, South Korea
Methods: acid hydrolysis, biological assays, UV, CC, centrifugation
- Article ID: 12307
Kobayashi MS, Han D, Packer L "Antioxidants and herbal extracts protect HT-4 neuronal cells against glutamate-induced cytotoxicity" -
Free Radical Research 32(2) (2000) 115-124
Antioxidant therapy has been shown to be beneficial in neurological disorders including Alzheimer's disease and cerebral ischemia. Glutamate-induced cytotoxicity in HT-4 neuronal cells has been previously demonstrated to be due to oxidative stress caused by depletion of cellular glutathione (GSH). The present study demonstrates that a wide variety of antioxidants inhibit glutamate-induced cytotoxicity in HT-4 neuronal cells. Low concentrations of alpha-tocopherol and its analogs were highly effective in protecting neuronal cells against cytotoxicity. Purified flavonoids and herbal extracts of Gingko biloba (EGb 761) and French maritime pine bark (Pycnogenol) were also effective. We have previously shown that pro-glutathione agents can spare GSH and protect cells from glutamate insult in a C6 glial cell model. The protective effects of nonthiol-based antioxidants tested in the HT-4 line were not mediated via GSH level modulation. In contrast, protective effects of thiol-based pro-glutathione agents alpha-lipoic acid (LA) and N-acetyl cysteine (NAC) corresponded with a sparing effect on GSH levels in glutamate-treated HT-4 cells. Glutamate-induced cytotoxicity in HT-4 cells is a useful model system for testing compounds or mixtures for antioxidant activity.
cytotoxicity, quercetin, antioxidation activity, rutin, HT-4 neuronal cells
NCBI PubMed ID: 10653482Publication DOI: 10.1080/10715760000300121Journal NLM ID: 9423872Publisher: London: Informa Healthcare
Correspondence: packer@socrates.berkeley.edu
Institutions: Membrane Bioenergetics Group, Department of Molecular and Cell Biology, University of California, Berkeley, USA, Department of Molecular Pharmacology and Toxicology, School of Pharmacy, University of Southern California, Los Angeles, USA
- Article ID: 12344
Lee SS, Chen WC, Chen CH "New jujubogenin glycosides from Colubrina asiatica" -
Journal of Natural Products 63(11) (2000) 1580-1583
Three new jujubogenin glycosides, namely, 3''-O-acetylcolubrin (1); 3'',2' "-O-diacetylcolubrin (2), and 3''-O-acetyl-6''-O-trans-crotonylcolubrin (3), were isolated from the leaves of Colubrina asiatica, in addition to the known colubrin, rutin, and kaempferol 3-O-rutinoside. Compounds 1-3 were isolated and purified via a combination of chromatographic procedures, and determined structurally using spectroscopic methods.
isolation, jujubogenin glycosides, Colubrina asiatica
NCBI PubMed ID: 11087616Publication DOI: 10.1021/np000225nJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: shoeilee@ha.mc.ntu.edu.tw
Institutions: School of Pharmacy, College of Medicine, National Taiwan University, Taipei, Taiwan, China
- Article ID: 12371
Inocencio C, Rivera D, Alcaraz F, Tomás-Barberán FA "Flavonoid content of commercial capers (Capparis spinosa, C. sicula and C. orientalis) produced in mediterranean countries" -
European Food Research and Technology 212 (2000) 70-74
The flavonol content of commercial capers (pickled flower buds of Capparis spinosa L., C. sicula Veill. in Duham. and C. orientalis Veill. in Duham.) produced in different Mediterranean countries (Spain, Italy, Greece, Turkey and Morocco) has been analysed. The content of quercetin 3-rutinoside, kaempferol 3-rutinoside; and kaempferol 3-rhamnosyl-rutinoside as well as the aglycones (quercetin and kaempferol) were evaluated by HPLC coupled with a diode-array detector. The free aglycones were not detected in the original flower buds, indicating that they were produced during the brining process. In addition, brining extracted most of the kaempferol 3-rhamnosyl rutinoside present in the original buds, this being a minor constituent in pickled capers. The average content of flavonoid glycosides in commercial capers was 5.18 mg/g fresh weight. When this value is converted to the corresponding aglycones (quercetin and kaempferol), capers provide an average of 3.86 mg/g fresh weight. A serving of capers (10 g) will provide 65 mg of flavonoid glycosides or the equivalent 40 mg of quercetin as aglycone.
flavonols, Capparis spinosa, Capparis sicula, capers
Publication DOI: 10.1007/s002170000220Journal NLM ID: 100957634Publisher: Berlin: Springer
Correspondence: fatomas@natura.cebas.csic.es
Institutions: Department of Botany, Biology, University of Murcia, Espinardo, Spain, Phytochemical Laboratory, Department of Food Science and Technology, CEBAS (CSIC), Murcia, Spain
Methods: HPLC, UV, extraction
- Article ID: 12373
Ito H, Koreishi M, Tokuda H, Nishino H, Yoshida T "Cypellocarpins A-C, phenol glycosides esterified with oleuropeic acid, from Eucalyptus cypellocarpa" -
Journal of Natural Products 63(9) (2000) 1253-1257
Three new phenol glycosides acylated with (+)-oleuropeic acid, cypellocarpins A (1), B (2), and C (3), along with seven known compounds, were isolated from the dried leaves of Eucalyptus cypellocarpa. Structures of the new compounds were determined on the basis of spectroscopic methods, including 2D NMR experiments and chemical degradation. These new compounds and a known related glucoside (7) showed potent in vitro antitumor-promoting activity in a short-term bioassay evaluating the inhibitory effect on Epstein-Barr virus early antigen activation induced by 12-O-tetradecanoyl phorbol 13-acetate (TPA). These compounds also suppressed an in vivo two-stage carcinogenesis induced with nitric oxide and TPA on mouse skin.
antitumor activity, cypellocarpins, Eucalyptus cypellocarpa, carcinogenesis, Epstein-Barr virus
NCBI PubMed ID: 11000030Publication DOI: 10.1021/np0001981Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: yoshida@pheasant.pharm.okayama-u.ac.jp
Institutions: Faculty of Pharmaceutical Sciences, Okayama University, Okayama, Japan, Kyoto Prefectural University of Medicine, Kyoto, Japan
Methods: 13C NMR, 1H NMR, methylation, inhibition studies, ESI-MS, biological assays, methanolysis, alkaline hydrolysis, UV, extraction, optical rotation measurement, CC, HR-ESI-MS, precipitation, evaporation, centrifugation, PTLC
- Article ID: 12379
Ivancheva S, Petrova A "A chemosystematic study of eleven Geranium species" -
Biochemical Systematics and Ecology 28(3) (2000) 255-260
The flavonoids of 11 species from six sections (Geranium, Batrachioides, Lucida, Unguiculata, Robertium, Erodioideae) of the genus Geranium have been studied. Quercetin and its derivatives were the most common aglycones with lesser amounts of kaempferol, myricetin and luteolin. Glycosylation was found mainly in the 3 or 4′ positions and to a lesser extent in the 7 position. Chemosystematic relationships are discussed. The occurrence of exudate flavonoids various methyl ether of kaempferol, quercetin and myricetin has been detected in all the 11 species surveyed.
flavonoid glycosides, chemosystematics, Geranium, flavonoid aglycones
Publication DOI: 10.1016/S0305-1978(99)00060-5Journal NLM ID: 0430442Publisher: Pergamon Press
Correspondence: Ivancheva S
Institutions: Institute of Botany, Bulgarian Academy of Sciences, Sofia, Bulgaria
Methods: TLC, extraction, CC, evaporation
- Article ID: 12406
Lin Y-L, Kuo Y-H, Shiao M-S, Chen C-C, Ou J-C "Flavonoid glycosides from Terminalia catappa L." -
Journal of the Chinese Chemical Society = Zhongguo hua hsueh hui hui zhi 47(1) (2000) 253-256
Under the inhibition of Cu+2-induced LDL oxidation-guided fractionation, two new flavone glycosides with galloyl substitution were isolated from the dried fallen leaves of Terminalia catappa L. Their structures were established as apigenin 6-C-(2″-O-galloyl)-β-D-glucopyranoside (1) and apigenin 8-C-(2″-O-galloyl)-β-D-glucopyranoside (2), together with four known flavone glycosides, isovitexin, vitexin, isoorientin, and rutin, on the basis of spectroscopic method. Compounds 1 and 2 showed significant antioxidative effects. Their IC50 were 2.1 and 4.5 μM, respectively.
Antioxidant, Combretaceae, Terminalia catappa L., dried fallen leaves, flavone glucopyranosides
Publication DOI: 10.1002/jccs.200000030Journal NLM ID: 16210600RPublisher: Taipei: Chinese Chemical Society
Institutions: National Research Institute of Chinese Medicine, Taipei, Taiwan, China, Department of Chemistry, National Taiwan University, Taipei, Taiwan, China, Department of Medical Research and Education, Veterans General Hospital, Taipei, Taiwan, China
Methods: biological assays, extraction, evaporation, centrifugation
- Article ID: 12430
Ma Y-L, Vedernikova I, Van den Heuvel H, Claeys M "Internal glucose residue loss in protonated O-diglycosyl flavonoids upon low-energy collision-induced dissociation" -
Journal of the American Society for Mass Spectrometry 11(2) (2000) 136-144
The low-energy collision-induced dissociation of protonated flavonoid O-diglycosides, i.e., flavonoid O-rutinosides and O-neohesperidosides, containing different aglycone types has been studied. The results indicate that the unusual [M+H-162]+ ion formed by internal glucose residue loss, which in a previous study was shown to be a rearrangement ion, is strongly dependent upon the aglycone type. For 7-O-diglycosides, the internal glucose loss is very pronounced for aglycones of the flavanone type, but is completely absent for aglycones of the flavone and flavonol types. Internal glucose residue loss was found to correspond to a minor fragmentation pathway for flavonol 3-O-diglycosides. A plausible mechanism is proposed based on proton mobilization from the aglycone to the disaccharidic part of the flavonoid O-diglycosides which is supported by theoretical calculations and model building.
NCBI PubMed ID: 10689666Publication DOI: 10.1016/S1044-0305(99)00133-6Journal NLM ID: 9010412Publisher: Elsevier
Correspondence: claeys@uia.ua.ac.be
Institutions: Department of Pharmaceutical Sciences, University of Antwerp (UIA), Antwerp, Belgium
Methods: MS
- Article ID: 12437
Mahmoud NN, Carothers AM, Grunberger D, Bilinski RT, Churchill MR, Martucci C, Newmark HL, Bertagnolli MM "Plant phenolics decrease intestinal tumors in an animal model of familial adenomatous polyposis" -
Carcinogenesis 21(5) (2000) 921-927
Epidemiological studies consistently indicate that consumption of fruits and vegetables lowers cancer risk in humans and suggest that certain dietary constituents may be effective in preventing colon cancer. Plant-derived phenolic compounds manifest many beneficial effects and can potentially inhibit several stages of carcinogenesis in vivo. In this study, we investigated the efficacy of several plant-derived phenolics, including caffeic acid phenethyl ester (CAPE), curcumin, quercetin and rutin, for the prevention of tumors in C57BL/6J-Min/+ (Min/+) mice. These animals bear a germline mutation in the Apc gene and spontaneously develop numerous intestinal adenomas by 15 weeks of age. At a dietary level of 0.15%, CAPE decreased tumor formation in Min/+ mice by 63%. Curcumin induced a similar tumor inhibition. Quercetin and rutin, however, both failed to alter tumor formation at dietary levels of 2%. Examination of intestinal tissue from the treated animals showed that tumor prevention by CAPE and curcumin was associated with increased enterocyte apoptosis and proliferation. CAPE and curcumin also decreased expression of the oncoprotein beta-catenin in the enterocytes of the Min/+ mouse, an observation previously associated with an antitumor effect. These data place the plant phenolics CAPE and curcumin among a growing list of anti-inflammatory agents that suppress Apc-associated intestinal carcinogenesis.
anticancer activity, phenolics, natural compounds, adenomatous polyposis
NCBI PubMed ID: 10783313Publication DOI: 10.1093/carcin/21.5.921Journal NLM ID: 8008055Publisher: Oxford: Irl Press At Oxford University Press
Correspondence: mbertagnolli@partners.org
Institutions: The New York Hospital-Cornell Medical Center, New York, USA, College of Physicians and Surgeons, Columbia–Presbyterian Cancer Center and School of Public Health, Columbia University, New York, USA, The Strang Cancer Prevention Center, New York, USA, Rutgers University Laboratory for Cancer Research, Piscataway, USA
Methods: biological assays
- Article ID: 12443
Marais JP, Mueller-Harvey I, Brandt EV, Ferreira D "Polyphenols, condensed tannins, and other natural products in Onobrychis viciifolia (sainfoin)" -
Journal of Agricultural and Food Chemistry 48(8) (2000) 3440-3447
An acetone/water extract of the fodder legume Onobrychis viciifolia afforded arbutin, kaempferol, quercetin, rutin, afzelin, the branched quercetin-3-(2(G)-rhamnosylrutinoside), the amino acid L-tryptophan, the inositol (+)-pinitol, and relatively high concentrations of sucrose (ca. 35% of extractable material). Acid-catalyzed cleavage of the condensed tannins with phloroglucinol afforded catechin, epicatechin and gallocatechin as the terminal and extender units, but epigallocatechin was only present in extender units. The condensed tannins in O. viciifolia presumably consist of hetero- and homopolymers containing both procyanidin and prodelphinidin units. Comparison of data from the present study and the literature suggests that sainfoin tannins have a highly variable composition with cis:trans ratios ranging from 47:53 to 90:10 and delphinidin:cyanidin ratios from 36:64 to 93:7. The composition of terminal and extender units in sainfoin tannins seems to be cultivar specific.
Onobrychis viciifolia; sainfoin; arbutin; sucrose; (+)-pinitol; tryptophan derivatives; flavonols; condensed tannins
NCBI PubMed ID: 10956131Publication DOI: 10.1021/jf000388hJournal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: dferreir@olemiss.edu
Institutions: National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, USA, Department of Chemistry, University of the Orange Free State, Bloemfontein, South Africa, Department of Agriculture, The University of Reading, Reading, UK
Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, TLC, HPLC, extraction, evaporation, centrifugation, HR-EI-MS
- Article ID: 12501
Morand C, Manach C, Crespy V, Rémésy C "Respective bioavailability of quercetin aglycone and its glycosides in a rat model" -
BioFactors 12(1-4) (2000) 169-174
A large number of flavonoids, mostly O-glycosides, are found in foods of plant origin. The bound sugar moiety is known to influence their bioavailability. We examined here the effect of the nature of the sugar on the absorption of the glycosides. Four groups of rats (n=6) received a meal containing 20 mg of quercetin equivalents supplied as aglycone, quercetin 3-glucoside, quercetin 3-rhamnoside or rutin. Plasma were hydrolysed by a βglucuronidase/sulfatase and analyzed by HPLC coupled to UV detection at 370 nm. Four hours after the beginning of the meal, the quercetin metabolites present in plasma were identical in all groups but their total concentrations were quite different. With pure quercetin the circulating levels were 11.7± 1.8 μM, but this level was three fold higher when quercetin was supplied as quercetin 3-glucoside (33.2± 3.5 μM). By contrast, the plasma concentrations of quercetin metabolites was quite low with the rutin meal (about 3 μM) and undetectable after the quercetin 3-rhamnoside meal. These data suggest that the 3-O-glucosylation improves the absorption of quercetin in the small intestine, whereas the binding of a rhamnose or of a glucose-rhamnose moiety to the aglycone markedly depressed its absorption. Additionnal experiments have shown that the higher plasma levels measured after the meal containing quercetin 3-glucoside compared to quercetin were maintained throughout a 24 hour period following the meal. In conclusion, the nature of the glycosylation markedly influences the efficiency of quercetin absorption in rats. Quercetin 3-glucose can be absorbed in the small intestine and is better absorbed than quercetin itself. By contrast, glycosides containing a rhamnose moiety could not be absorbed in the small intestine.
quercetin, quercetin glycosides, intestinal absorption, plasma metabolites
NCBI PubMed ID: 11216481Publication DOI: 10.1002/biof.5520120127Journal NLM ID: 8807441Publisher: Oxford; Washington, DC: IRL Press, International Union of Biochemistry
Correspondence: cmorand@clermont.inra.fr
Institutions: Unité des Maladies Métaboliques et des Micronutriments, INRA Theix, Ceyrat, France
Methods: biological assays, HPLC
- Article ID: 12502
Moreira AS, Spitzer V, Schapoval EES, Schenkel EP "Antiinflammatory activity of extracts and fractions from the leaves of Gochnatia polymorpha" -
Phytotherapy Research 14(8) (2000) 638-640
The aqueous and ethanol extracts from the leaves of Gochnatia polymorpha and further fractions obtained from the latter extract using solvents with increasing polarity, including its aqueous residue and the amino acid, 4-hydroxy-N-methyl-proline were investigated by carrageenin-induced pedal oedema formation. It was shown that the aqueous and ethanol extracts and the ethyl acetate fraction demonstrated significant antiinflammatory activity. The chemical investigation of the latter fraction revealed the presence of caffeic acid, chlorogenic acid, 3-0-methylquercetin, hyperosid and rutin. The amino acid 4-hydroxy-N-methyl-proline, a nonprotein amino acid that has not been reported before in the Asteraceae was isolated as a major compound and identified by spectroscopic methods.
Gochnatia polymorpha; antiinflammatory activity; flavonoids; 4-hydroxy-N-methyl-proline
NCBI PubMed ID: 11114003Publication DOI: 10.1002/1099-1573(200012)14:8<638::aid-ptr681>3.0.co;2-qJournal NLM ID: 8904486Publisher: Chichester: Wiley
Institutions: Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Porto Alegre, Brazil
Methods: biological assays
- Article ID: 12514
Muruganandam AV, Bhattacharya SK, Ghosal S "Indole and flavonoid constituents of Wrightia tinctoria, W. tomentosa and W. coccinea" -
Indian Journal of Chemistry. Section B: Organic Including Medicinal 39(2) (2000) 125-131
Members of the genus Wrightia, viz. W. tinctoria, W. tomentosa and W. coccinea, have been investigated for their chemical constituents with a view to locating their bioactive principles. Indigotin 3, indirubin 6, tryptanthrin 8, isatin 5, anthranillate 7 and rutin 9 have been isolated and identified as major constituents of W. tinctoria and W. tomentosa. Anthranillate 7 and rutin 9 are the major constituents of W. coccinea. The identities of these compounds have been established by comprehensive chromatographic (HPTLC, HPLC) and spectroscopic (UV-VIS, IR, EI-MS) techniques, using markers and by synthesis, where possible. While indigotin is found to be native in the living plants (in fresh leaves), indirubin was found to be an artifact formed only during drying process after harvesting of the leaves. This transformation is presumably caused by the intact hydrolytic enzyme system(s) and by autoxidation. Seasonal variation studies of the chemical constituents of leaves, using HPTLC and HPLC analyses, revealed similar variation patterns in the three species. The concentration of indigotin-indirubin combination steadily increases from August to November. In contrast, concentration of isatin and anthranillate increases in the months of December and January, at the expense of indigotin-indirubin. Isatin is produced by the autoxidation of indigotin. Tryptanthrin concentration also increases, periodically, in May (at the expense of isatin) and in January. Plausible pathways for the formation of these indole metabolites are appraised on the basis of circumstantial and synthetic evidence.
flavonoids, indican, indole constituents, Wrightia genus
Journal NLM ID: 7613422WWW link: http://nopr.niscpr.res.in/handle/123456789/22492Publisher: New Delhi, Council of Scientific & Industrial Research
Institutions: Department of Pharmacology, Institute of Medical Sciences, Banaras Hindu University, Varanasi, India, R&D Center, Indian Herbs Ltd., Saharanpur, India
Methods: IR, UV, spectrophotometry, HLC
- Article ID: 12522
Ng TB, Liu F, Wang ZT "Antioxidative activity of natural products from plants" -
Life Sciences 66(8) (2000) 709-723
A variety of flavonoids, lignans, an alkaloid, a bisbenzyl, coumarins and terpenes isolated from Chinese herbs was tested for antioxidant activity as reflected in the ability to inhibit lipid peroxidation in rat brain and kidney homogenates and rat erythrocyte hemolysis. The pro-oxidant activities of the aforementioned compounds were assessed by their effects on bleomycin-induced DNA damage. The flavonoids baicalin and luteolin-7-glucuronide-6'-methyl ester, the lignan 4'-demethyldeoxypodophyllotoxin, the alkaloid tetrahydropalmatine, the bisbenzyl erianin and the coumarin xanthotoxol exhibited potent antioxidative activity in both lipid peroxidation and hemolysis assays. The flavonoid rutin and the terpene tanshinone I manifested potent antioxidative activity in the lipid peroxidation assay but no inhibitory activity in the hemolysis assay. The lignan deoxypodophyllotoxin, the flavonoid naringin and the coumarins columbianetin, bergapten and angelicin slightly inhibited lipid peroxidation in brain and kidney homogenates. It is worth stressing that the compounds with antioxidant effects in this assay, with the exception of tetrahydropalmatin and tanshinone I, have at least one free aromatic hydroxyl group in structure. Obviously, the aromatic hydroxyl group is very important for antioxidative effects of the compounds. None of the compounds tested exerted an obvious pro-oxidant effect.
plant, Antioxidant, hemolysis, peroxidation
NCBI PubMed ID: 10680579Publication DOI: 10.1016/s0024-3205(99)00642-6Journal NLM ID: 0375521Publisher: Amsterdam: Elsevier
Correspondence: Ng TB
Institutions: Department of Pharmacognosy, China Pharmaceutical University, Nanjing, China, Department of Microbiology, Nankai University, Tianjin, China, Department of Biochemistry, Faculty of Medicine, The Chinese University of Hong Kong, Hong Kong, China
Methods: biological assays
- Article ID: 12536
Nishibe S, Chiba M, Hisada S "Studies on the Chinese crude drug "Forsythiae Fructus." I. On the constituents of Forsythiae Fructus on the market" -
Yakugaku Zasshi = Journal of the Pharmaceutical Society of Japan [Japanese] 97(10) (1977) 1134-1137
The constituents of the fruits of Forsythia suspensa VAHL (Oleaceae) on the market were investigated. Betulinic acid, oleanolic acid, phillygenin, (+)-pinoresinol, phillyrin, and rutin were isolated from the methanolic extract and respectively identified with authentic samples.
Publication DOI: 10.1248/YAKUSHI1947.97.10_1134Journal NLM ID: 0413613Publisher: Tokyo: Nihon Yakugakkai
Institutions: Faculty of Pharmaceutical Sciences, Higashi Nippon Gakuen University, Ishikari-Tobetsu, Japan
Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, TLC, HPLC, extraction, evaporation, centrifugation, HR-EI-MS
- Article ID: 12552
Nyiredy S "Solid-liquid extraction strategy on the basis of solvent characterization" -
Chromatographia 51 (2000) ID S288-S296
Different solvents used for extraction are characterized on the basis of the Snyder theory. The individual solvent strength (si) and selectivity values (sv) of the solvents are used to formulate an extraction strategy by use of selected solvents, in a manner similar to that used for the computer-aided HPLC and TLC “PRISMA” mobile phase optimization procedures. After a pre-assay using the nine proposed solvents, twelve measurements are necessary to obtain the global optimum. The new method allows successful solid-liquid extraction of compounds from biological matrices such as medicinal and aromatic plants. Data obtained from furocoumarin isomers and flavonoid glycosides extracted from different medicinal and aromatic plants are used to demonstrate the validity of the method. The structures and properties of the compounds to be extracted do not have to be known for the procedure to be used.
solid-liquid extraction, extraction strategy, solvent characterization, "PRISMA" system, phytopharmaceuticals
Publication DOI: 10.1007/BF02492820Journal NLM ID: 0316520Publisher: Friedr. Vieweg Und Sohn Verlags Gmbh
Institutions: Research Institute for Medicinal Plants, Budakalász, Hungary
Methods: TLC, HPLC, extraction
- Article ID: 12578
Palomino O, Gómez-Serranillos MP, Slowing K, Carretero E, Villar A "Study of polyphenols in grape berries by reversed-phase high-performance liquid chromatography" -
Journal of Chromatography A 870(1-2) (2000) 449-451
Several polyphenols have been tested in grape berries from Spain. The flavonoid content is important because of the pharmacological properties of these compounds, whereas resveratrol has been proved to be an antifungal, antiinflammatory and an anticarcinogenic compound. A reversed-phase HPLC method has been developed and applied to determine resveratrol, quercetine, quercitrine and rutine content in several grape berries samples in a single analysis. Covering the grapes with a preservative paper yields a healthier product, but one which has a lower polyphenol content than unprotected grapes.
fruits; food analysis; polyphenols; flavonoids
NCBI PubMed ID: 10722101Publication DOI: 10.1016/s0021-9673(99)01225-xJournal NLM ID: 9318488Publisher: Amsterdam; New York: Elsevier
Correspondence: Gómez-Serranillos MP
Institutions: Department of Pharmacology, Faculty of Pharmacy, Universidad Complutense de Madrid, Madrid, Spain
Methods: extraction, RP-HPLC
- Article ID: 12612
Rauha J-P, Remes S, Heinonen M, Hopia A, Kähkönen M, Kujala T, Pihlaja K, Vuorela H, Vuorela P "Antimicrobial effects of Finnish plant extracts containing flavonoids and other phenolic compounds" -
International Journal of Food Microbiology 56(1) (2000) 3-12
Plant phenolics, especially dietary flavonoids, are currently of growing interest owing to their supposed functional properties in promoting human health. Antimicrobial screening of 13 phenolic substances and 29 extracts prepared from Finnish plant materials against selected microbes was conducted in this study. The tests were carried out using diffusion methods with four to nine microbial species (Aspergillus niger, Bacillus subtilis, Candida albicans, Escherichia coli, Micrococcus luteus, Pseudomonas aeruginosa, Saccharomyces cerevisiae, Staphylococcus aureus and Staphylococcus epidermidis). Flavone, quercetin and naringenin were effective in inhibiting the growth of the organisms. The most active plant extracts were purple loosestrife (Lythrum salicaria L.) against Candida albicans, meadowsweet (Filipendula ulmaria (L.) Maxim.), willow herb (Epilobium angustifolium L.), cloudberry (Rubus chamaemorus L.) and raspberry (Rubus idaeus L.) against bacteria, and white birch (Betula pubescens Ehrh.), pine (Pinus sylvestris L.) and potato (Solanum tuberosum. L.) against gram-positive Staphylococcus aureus.
antimicrobial activity; inhibition; flavonoids; phenolics; plants; berries
NCBI PubMed ID: 10857921Publication DOI: 10.1016/s0168-1605(00)00218-xJournal NLM ID: 8412849Correspondence: pia.vuorela@helsinki.fi
Institutions: Department of Pharmacy, University of Helsinki, Division of Pharmacognosy, Helsinki, Finland, Department of Applied Chemistry and Microbiology, University of Helsinki, Division of Food Chemistry, Helsinki, Finland, Department of Chemistry, Laboratory of Physical Chemistry, University of Turku, Turku, Finland
- Article ID: 12624
Ross SA, Ziska DS, Zhao K, ElSohly MA "Variance of common flavonoids by brand of grapefruit juice" -
Fitoterapia 71(2) (2000) 154-161
Nine commercial brands of grapefruit juice were analyzed for their flavonoid content by HPLC to determine if significant brand-to-brand variance in grapefruit juice flavonoid content exists. Flavonoid glycosides narirutin, naringin, hesperidin, neohesperidin, didymin, and poncirin have been identified in all the grapefruit juices examined. The aglycone quercetin was detected in only two brands. All the juices were free from methoxylated flavonoid aglycones. There was a significant difference in the amounts of total flavonoids and individual flavonoids in the nine brands. The concentration of total flavonoids ranged between 19.44 and 84.28 mg/100 ml juice. Naringin was found to be the major flavonoid followed by narirutin and hesperidin. Their concentrations ranged from 14.56 to 63.8; 2.25 to 12.20; and 0.24 to 3.12 mg/100 ml juice, respectively.
grapefruit juice; flavonoids; HPLC
NCBI PubMed ID: 10727812Publication DOI: 10.1016/s0367-326x(99)00131-8Journal NLM ID: 16930290RPublisher: Elsevier
Correspondence: dziska@pharmacy.umsmed.edu
Institutions: The National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, Mississippi, USA, Department of Pharmacognosy, University of Mississippi, School of Pharmacy, Mississippi, USA, Department of Clinical Pharmacy Practice, University of Mississippi, School of Pharmacy, Mississippi, USA, Department of Pharmaceutics, University of Mississippi, School of Pharmacy, Mississippi, USA
- Article ID: 12625
Rundlöf T, Olsson E, Wiernik A, Back S, Aune M, Johansson L, Wahlberg I "Potential nitrite scavengers as inhibitors of the formation of N-nitrosamines in solution and tobacco matrix systems" -
Journal of Agricultural and Food Chemistry 48(9) (2000) 4381-4388
The ability of 20 compounds, all but one tobacco constituents, to inhibit the formation of tobacco-specific N-nitrosamines (TSNA) was investigated in buffer and detergent solution and in tobacco midrib and lamina systems. In solution at pH 5.5, ascorbic acid and the phenolic acids caffeic and ferulic acid were the most potent inhibitors of the reaction between nornicotine and nitrite, with nearly complete inhibition at molar ratios test compound/nitrite > 1:1. Also, cysteine > dihydrocaffeic acid > protocatechuic acid approximately catechin acted as strong inhibitors with >90% inhibition at a ratio of 3:1. Lower inhibitions were observed with chlorogenic acid > p-coumaric acid > sclareol > serine. Rutin showed an inhibition of 34% at a ratio of 0.1:1. Sclareol, alanine, proline, and serine did not significantly affect the N-nitrosonornicotine (NNN) formation. alpha-Tocopherol and glutathione enhanced NNN formation at pH 5.5 but were inhibitors at pH 3. Cinnamic acid, vanillic acid, eugenol, and esculin enhanced NNN formation. Increased NNN formation was also observed for dihydrocaffeic acid, chlorogenic acid, protocatechuic acid, and catechin at a less-than-equimolar ratio of test compound to nitrite. The tobacco matrix experiments were performed with air-cured, ground tobacco midrib and lamina. Caffeic acid, ferulic acid, dihydrocaffeic acid and catechin were potent inhibitors of the formation of TSNA in the midrib as well as in the lamina. Also protocatechuic acid, glutathione, ascorbic acid, p-coumaric acid, chlorogenic acid and cysteine were inhibitors, while alpha-tocopherol and rutin inhibited the reaction in the midrib but not in the lamina. Cinnamic acid, vanillic acid, eugenol, alanine, proline and serine showed small effects only. The molar ratio of secondary alkaloid(s)/nitrite in the test systems were 0.1:1 (solution), approximately 0.25:1 (midrib), and approximately 1:1 (lamina) and is most likely the major contributor to the observed order of inhibition potency (solution > midrib > lamina) of the test compounds. The vicinal phenolic hydroxyl groups of polyphenols and the simultaneous presence of a phenol group and an olefinic bond in hydroxycinnamic acids were the most characteristic structural elements of the potent inhibitors.
Tobacco-specific N-nitrosamines; nitrosation; nornicotine; secondary alkaloids; nitrite scavengers; ascorbic acid; R-tocopherol; phenolic acids; flavonoids; coumarins, amino acids; tobacco matrix; midrib; lamina
NCBI PubMed ID: 10995367Publication DOI: 10.1021/jf000147+Journal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: inger.wahlberg@swedishmatch.se
Institutions: Research & Analysis, Swedish Match, Stockholm, Sweden
Methods: biological assays
- Article ID: 12629
Sahpaz S, Gupta MP, Hostettmann K "Triterpene saponins from Randia formosa" -
Phytochemistry 54(1) (2000) 77-84
Seven new triterpenoid saponins, randiasaponins I (1), II (2), III (3), IV (4), V (5), VI (6) and VII (7) as well as two known ones, ilexoside XXVII (8) and ilexoside XXXVII (9), were isolated from the methanolic extract of the leaves of Randia formosa. The structures of the new saponins were established as 3-O-α-L-arabinopyranosyl-3β,19α,23-trihydroxyursa-12,20(30)-dien-28-oic acid 28-β-D-glucopyranosyl ester (1), 3-O-β-D-glucopyranosyl-(1 → 3)-α-L-arabinopyranosyl rotundic acid (2), 3-O-β-D-glucopyranosyl-(1 → 3)-α-L-arabinopyranosyl pomolic acid 28-β-D-glucopyranosyl ester (3), 3-O-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl pomolic acid 28-β-D-glucopyranosyl ester (4), 3-O-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl siaresinolic acid 28-β-D-glucopyranosyl ester (5), 3-O-α-L-arabinopyranosyl ilexosapogenin A 28-β-D-glucopyranosyl ester (6), and 3-O-β-D-glucopyranosyl ilexosapogenin A 28-β-D-glucopyranosyl ester (7), based on spectral and chemical evidence. Besides the saponins, two common flavonoids kaempferol 3-O-rutinoside and rutin were also isolated.
pomolic acid, siaresinolic acid, triterpenoid saponins, 3β, Rubiaceae, rotundic acid, ilexosapogenin A, Randia formosa, 19α, 23-trihydroxy-ursa-12, 20(30)-dien-28-oic acid
NCBI PubMed ID: 10846751Publication DOI: 10.1016/s0031-9422(00)00034-0Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: kurt.hostettmann@ipp.unil.ch
Institutions: Institut de Pharmacognosie et Phytochimie, Université de Lausanne, Lausanne, Switzerland, CIFLORPAN, Faculdad de Farmacia, Universidad de Panama, Panama City, Panama
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, acid hydrolysis, HPLC, alkaline hydrolysis, extraction, CI-MS, HR-ESI-MS, evaporation, centrifugation
- Article ID: 12633
Sakushima A, Nishibe S, Hisada S, Noro Y, Hisada Y "Studies on the constituents of Apocynaceae plants. Isolation of flavonol glycosides and some other components from the leaves of Cerbera manghas L." -
Yakugaku Zasshi = Journal of the Pharmaceutical Society of Japan [Japanese] 96(8) (1976) 1046-1048
The methanol extract of the leaves of Cerbera manghas L. was treated and from the ethyl acetate fraction, succinic acid, nicotiflorin, and rutin, and from the aqueous layer L-(+)-bornesitol were isolated and identified respectively with authentic samples.
NCBI PubMed ID: 1035940Publication DOI: 10.1248/yakushi1947.96.8_1046Journal NLM ID: 0413613Publisher: Tokyo: Nihon Yakugakkai
Institutions: Faculty of Pharmaceutical Sciences, Higashi Nippon Gakuen University, Ishikari-Tobetsu, Japan, Faculty of Pharmacy, Meijo University, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, extraction, optical rotation measurement, CC, centrifugation
- Article ID: 12656
Sarni-Manchado P, Le Roux E, Le Guernevé C, Lozano Y, Cheynier V "Phenolic composition of litchi fruit pericarp" -
Journal of Agricultural and Food Chemistry 48(12) (2000) 5995-6002
Litchi (Litchi chinensis, Sapindaceae) is a nonclimacteric subtropical fruit that, once harvested, loses its red pericarp color because of browning reactions probably involving polyphenols. Low-pressure chromatography, high-pressure liquid chromatography, UV-visible spectral analysis, mass spectrometry, and nuclear magnetic resonance studies have allowed the determination and quantification of the polyphenolic composition of litchi pericarp. Litchi skins contain significant amounts of polyphenolic compounds. The principal characteristic of the litchi skin polyphenolic compounds is their ortho-diphenolic structure, which gives them high oxidability. Four major pigments were formally identified as cyanidin 3-rutinoside, cyanidin glucoside, quercetin 3-rutinoside (rutin), and quercetin glucoside. The tannin content was characterized after the depolymerization thiolysis reaction. Tannins (polymeric proanthocyanidins) are mainly constituted with epicatechin units linked by A- and B-type bonds. The different phenolic compounds of litchi cv. Kwai Mi were quantified by HPLC. Condensed tannins were the most abundant (4 mg/g of fresh skin), followed by epicatechin and procyanidin A2 (1.7 and 0.7 mg/g of fresh pericarp, respectively). The amount of anthocyanins was found to be comparable to that of flavonols, with a value of approximately 0.4 mg/g of fresh pericarp.
Litchi; polyphenols; anthocyanins; flavonols; proanthocyanidins; condensed tannins; characterization; quantification
NCBI PubMed ID: 11312772Publication DOI: 10.1021/jf000815rJournal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: sarni@ensam.inra.fr
Institutions: Unité de Recherche des Produits de la Vigne, INRA, Montpellier, France, CIRAD, Montpellier, France
Methods: 13C NMR, 1H NMR, IR, TLC, HPLC, UV, extraction, optical rotation measurement, melting point determination, HR-FAB-MS
- Article ID: 12683
Sharaf M, El-Ansari MA, Saleh NAM "Quercetin triglycoside from Capparis spinosa" -
Fitoterapia 71(1) (2000) 46-49
In addition to rutin, quercetin 3-O-glucoside and quercetin 3-O-glucoside-7-O-rhamnoside, the methanolic extract of the aerial parts of Capparis spinosa yielded the new flavonoid quercetin 3-O-[6′″-α-l-rhamnosyl-6″-β-d-glucosyl]-β-d-glucoside (1).
Capparis spinosa; flavonoids
NCBI PubMed ID: 11449469Publication DOI: 10.1016/s0367-326x(99)00116-1Journal NLM ID: 16930290RPublisher: Elsevier
Correspondence: sharafali@hotmail.com
Institutions: Phytochemistry and Plant Systematics Department, National Research Centre, Cairo, Egypt
- Article ID: 12704
Smirnova LP, Nikolaeva SS, Bykov VA, Yakovleva LV, Rebrov LB, Rumyantseva NV "Application of the rutin standard sample in analysis of related raw plant materials, vitamin compositions, and phytopreparations" -
Pharmaceutical Chemistry Journal 34 (2000) 28-30
Rutin is one of the most widespread flavonoid compounds in plants; it occurrs especially frequently in the leaves of higher plants. In commercial practice, this substance is usually isolated from Sophora japonica (pagoda tree), the flowers and flower buds of which contain up to 20% rutin. Rutin is capable of controlling the permeability of capillaries, for which reason this compound is included in P-vitamin compositions. The alcohol solutions of rutin obey the Lambert-Bouguer-Beer law in a broad range of optical densities and retain stable optical absorption properties for about a one-month storage period. Due to this circumstance and the availability of rutin, this compound is employed more frequently than other γ-pyrones as a reference substance in the analysis of drugs and for the standardization of raw plant materials and phytopreparations with respect to the total content of phenols, in particular, the sum of flavonoids. In Russia, the State Standard Sample of rutin is obtained from a readily available domestic natural material - the herbs of common buckwheat. The rutin standard produced at the VILAR according to the State Technological Conditions TU 64-4-127-96 satisfies all present-day requirements of the State Pharmacopoeia and the WHO recommendations, representing a high-purity preparation characterized by modern analytical techniques, including UV spectrophotometry, 1H NMR spectroscopy, and HPLC. However, work with rutin standards is complicated by the high hygroscopicity of this substance, the water content being extremely sensitive to the hydrothermal conditions in the ambient medium. As is known, an uncertainty in determining water content in the standard sample may cancel all advantages gained from the use of high-purity reference substances in HPLC, TLC, or spectroscopic analyses. Previously [1], we have reported on the hygroscopicity of rutin investigated by DSC in the course of drying and water absorption, in combination with some other aquametric and gravimetric techniques. The main conclusion drawn from the study was the requirement of permanently controlling water content in the standard sample used in the analytical work. However, the experimental conditions studied in that work were rather different from those encountered in pharmaceutical practice. Indeed, small (5-8 mg) samples sealed in aluminum cells and studied under nitrogen flow conditions minimized the contact of rutin with the environment. The purpose of this work was to study the behavior of rutin in contact with water vapor under real analytical conditions simulating those stipulated by the State Pharmacopoeia (XI Ed., RSP-XI) and special Pharmacopoeial Clauses. Our recommendations concerning application of the rutin standard would allow analysts to avoid errors caused by the uncontrolled water sorption by rutin.
rutin, water sorption, ambient medium, equilibrium water content, common buckwheat
Publication DOI: 10.1007/BF02524555Journal NLM ID: 0323156Publisher: New York: Springer US
Institutions: Scientific-Research Center of Biomedical Technologies, State Research Institute of Medical and Aromatic Plants (VILAR), Moscow, Russia
Methods: gravimetry
- Article ID: 12711
Souleman AMA, El-Moussalamy AMD "Chemical investigation of the constitutive phenolics of Rosa arabica; the structure of a new dimeric phenolic glycoside" -
Natural Product Sciences 6(2) (2000) 82-85
The aqueous ethanolic whole plant extract of Rosa arabica was found to contain the new natural dimeric phenolic compound, ellagic acid 3,3'-dimethyl ether 4−O−α−rhamnopyranoside, 9, along with ten known phenolic metabolites (1-8, 10 and 11). Structures of all compounds (1-11) were established by routine methods of analysis and confirmed by FAB-MS, 1H and 13C NMR spectral analysis.
NMR, FAB-MS, rosaceae, Rosa arabica, dimeric phenolic glycoside, ellagic acid 3, 3'-dimethyl ether 4−O−α−rhamnopyranoside
Journal NLM ID: 9714997WWW link: http://kpubs.org/article/articleMain.kpubs?articleANo=E1HSBY_2000_v6n2_82Publisher: Seoul, Korea: Korean Society of Pharmacognosy
Institutions: National Research Centre, Cairo, Egypt, Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt
Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, enzymatic hydrolysis, acid hydrolysis, HPLC, UV, extraction, optical rotation measurement, melting point determination, HR-FAB-MS
- Article ID: 12721
Strick R, Strissel PL, Borgers S, Smith SL, Rowley JD "Dietary bioflavonoids induce cleavage in the MLL gene and may contribute to infant leukemia" -
Proceedings of the National Academy of Sciences of the USA 97(9) (2000) 4790-4795
Chromosomal translocations involving the MLL gene occur in about 80% of infant leukemia. In the search for possible agents inducing infant leukemia, we identified bioflavonoids, natural substances in food as well as in dietary supplements, that cause site-specific DNA cleavage in the MLL breakpoint cluster region (BCR) in vivo. The MLL BCR DNA cleavage was shown in primary progenitor hematopoietic cells from healthy newborns and adults as well as in cell lines; it colocalized with the MLL BCR cleavage site induced by chemotherapeutic agents, such as etoposide (VP16) and doxorubicin (Dox). Both in vivo and additional in vitro experiments demonstrated topoisomerase II (topo II) as the target of bioflavonoids similar to VP16 and Dox. Based on 20 bioflavonoids tested, we identified a common structure essential for topo II-induced DNA cleavage. Reversibility experiments demonstrated a religation of the bioflavonoid as well as the VP16-induced MLL cleavage site. Our observations support a two-stage model of cellular processing of topo II inhibitors: The first and reversible stage of topo II-induced DNA cleavage results in DNA repair, but also rarely in chromosome translocations; whereas the second, nonreversible stage leads to cell death because of an accumulation of DNA damage. These results suggest that maternal ingestion of bioflavonoids may induce MLL breaks and potentially translocations in utero leading to infant and early childhood leukemia.
doxorubicin, acute myelogenous leukemia, acute lymphoblastic leukemia, etoposide, topoisomerase II
NCBI PubMed ID: 10758153Publication DOI: 10.1073/pnas.070061297Journal NLM ID: 7505876Publisher: National Academy of Sciences
Correspondence: Strick R
; Strissel PL
Institutions: University of Chicago, Department of Medicine, Section of Hematology/Oncology, Chicago, IL, USA
Methods: biological assays
- Article ID: 12751
Tattini M, Gravano E, Pinelli P, Mulinacci N, Romani A "Flavonoids accumulate in leaves and glandular trichomes of Phillyrea latifolia exposed to excess solar radiation" -
New Phytologist 148(1) (2000) 69-77
Experiments were conducted on Phillyrea latifolia plants grown under a dense overstorey of Pinus pinea (shade plants) or on seashore dunes (sun plants) in a coastal area of Tuscany (42° 46′ N, 10° 53′ E). Total integrated photon flux densities averaged 1.67 and 61.4 m mol/m^2/d for shade and sun sites, respectively. A leaf morphological–structural analysis, a qualitative and quantitative analysis of phenylpropanoids of leaf tissue and leaf surface, and a histochemical localization of flavonoids were conducted. The area of sun leaves reached 57% of that of shade leaves, whereas leaf angle (β), sclerophylly index (ratio of leaf d. wt:leaf area), and trichome frequency (trichome number mm−2 ) were markedly greater in leaves exposed to full solar radiation than in leaves acclimated to shade. The total thickness of sun leaves was 78% higher than that of shade leaves, mostly owing to a greater development of both palisade parenchyma and spongy mesophyll. The concentration, but not the composition, of leaf tissue phenylpropanoids varied significantly between sun and shade leaves, with a marked increase in flavonoid glycosides in sun leaves. Flavonoids occurred almost exclusively in the upper epidermal cells of shade leaves. By contrast, flavonoids largely accumulated in the upper and lower epidermis, as well as in the mesophyll tissue of leaves that were acclimated to full sunlight. Flavonoid glycosides were found exclusively in the secretory products of glandular trichomes of P. latifolia leaves exposed to high levels of light; luteolin 7-O- glucoside and quercetin 3-O-rutinoside were the major constituents. By contrast, verbascoside and an unidentified caffeic acid derivative constituted 72% of total phenylpropanoids secreted by glandular trichomes of shade leaves, whereas they were not detected in glandular trichomes of sun leaves. These findings suggest that the light-induced synthesis of flavonoids in glandular trichomes of P. latifolia probably occurs in situ and concomitantly inactivates other branch pathways of the general phenylpropanoid metabolism. This is the first report of the key role of glandular trichomes and of flavonoid glycosides in the integrated mechanisms of acclimation of P. latifolia to excess light.
phenylpropanoids, flavonol glycosides, Oleaceae, fluorescence microscopy, glandular trichomes
NCBI PubMed ID: 33863030Publication DOI: 10.1046/j.1469-8137.2000.00743.xJournal NLM ID: 9882884Publisher: Blackwell Publishing
Correspondence: tattini@ipsl.fi.cnr.it
Institutions: Dipartimento di Scienze Farmaceutiche, Università di Firenze, Florence, Italy, Istituto sulla Propagazione delle Specie Legnose - Consiglio Nazionale delle Ricerche, Scandicci, Italy, Dipartimento di Biologia Vegetale, Università di Firenze, Florence, Italy
Methods: ESI-MS, HPLC, UV, extraction, HPTLC, HPLC-MS, spectrophotometry
- Article ID: 12881
Yu SJ, Abo-Elghar GE "Allelochemicals as inhibitors of glutathione S-transferases in the fall armyworm" -
Pesticide Biochemistry and Physiology 68(3) (2000) 173-183
Glutathione S-transferases (GSTs) isolated from larval midguts of the fall armyworm, Spodoptera frugiperda, were used to study their sensitivity to inhibition by 44 chemicals, most of which were plant allelochemi cals. Many flavonoids, other phenols, and α,β-unsaturated carbonyl compounds were potent inhibitors of the enzymes. For the flavonoids, apigenin was the best inhibitor among those studied, showing an I50 value of 0.82 μM. In general, flavonols exhibited higher inhibitory potencies than flavones; flavonoid glycosides were less inhibitory than their corresponding aglycones. In the case of phenols, tannic acid was the best inhibitor among those tested, showing an I50 value of 0.2 μM. The organotin compound chlorotriphenyltin was an potent as tannic acid in inhibiting the transferases. For the αβ-unsaturated carbonyl compounds, ethacrynic acid was the most potent inhibitor among those examined, showing an I50 value of 0.15 μM. However, the isothiocyanates were found to be marginal inhibitors of GSTs. GSTs isolated from larval fat bodies showed differential sensitivity to inhibition by some selected inhibitors compared with midgut GSTs. Kinetic studies of midgut GSTs revealed that ellagic acid exhibited a noncompetitive inhibition toward 1-chloro-2, 4-dinitrobenzene (CDNB) but a competitive inhibition toward glutathione (GSH). In contrast, inhibition by tannic acid and ethacrynic acid were noncompetitive toward both CDNB and GSH. Diethyl maleate did not affect GSH levels in midguts when larvae were topically treated with this compound for up to 24 h.
inhibition, flavonoids, glutathione S-transferase, Spodoptera frugiperda
Publication DOI: 10.1006/pest.2000.2514Journal NLM ID: 1301573Publisher: New York: Academic Press
Institutions: Department of Entomology and Nematology, University of Florida, Gainesville, USA
Methods: biological assays
- Article ID: 12921
Toker G, Türköz S, Erdemoglu N "High performance liquid chromatographic analysis of rutin in plants, I." -
Die Pharmazie 53(7) (1998) 494-495
Journal NLM ID: 9800766Publisher: Eschborn: Govi-Verlag Pharmazautischer Verlag
Institutions: Department of Pharmacognosy, Faculty of Pharmacy, University of Gazi, Ankara, Turkey
Methods: HPLC
Expand this compound
Collapse this compound
2. Compound ID: 22453
Structure type: monomer
C21H20O11
Trivial name: quercitrin, baohuoside-II, quercetin 3-rhamnoside, quercetin 3-O-rhamnoside
Compound class: saponin glycoside, glycoside, flavonoid glycoside, flavonol glycoside
Contained glycoepitopes: IEDB_136105,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 9204
Liang HR, Vuorela P, Vuorela H, Hiltunen R "Isolation and immunomodulatory effect of flavonol glycosides from Epimedium hunanense" -
Planta Medica 63(4) (1997) 316-319
The ethyl acetate and n-butanol fractions from aerial parts of E. hunanense were initially screened to find active fractions with immunomodulatory activity. Nine compounds, tricin (1), luteolin (2), thalictoside (3), icariin I (4), baohuoside I (5), quercitrin (6), icariin (7), epimedin C (8), and B (9) were isolated from this species for the first time, and 3 was isolated for the first time from flavonoid extracts of the genus. Their structures were established by chemical and spectroscopic methods. The immunomodulatory effects of the n-butanol fraction and epimedin C isolated from the fraction were investigated. Hydrocortisone acetate (HCA) was used as an immunosuppressant to inhibit the immune response of mice. The n-butanol fraction and epimedin C significantly enhanced the response of spleen antibody-forming cells (SAFC) to near normal in the mice treated with HCA. They also significantly enhanced lymphocyte proliferation and caused a significant recovery of interleukin-2 (IL-2) production in the mice inhibited with HCA. In conclusion, they are active principles with immunoenhancing effects.
flavonol glycosides, Epimedium hunanense, immunoenhancing effect, spleen antibody-forming cells (SAFC)
NCBI PubMed ID: 9270375Publication DOI: 10.1055/s-2006-957690Journal NLM ID: 0066751Publisher: George Thieme
Institutions: Pharmacognosy Division, Department of Pharmacy, University of Helsinki, Helsinki, Finland
Methods: 13C NMR, 1H NMR, IR, FAB-MS, biological assays, radiolabeling, radioactivity measurement, HPLC, UV, extraction, CC, cytokine production, centrifugation, recrystallization
- Article ID: 10734
Pietta P, Mauri P, Bruno A, Zini L "High-performance liquid chromatography and micellar electrokinetic chromatography of flavonol glycosides from Tilia" -
Journal of Chromatography A 638 (1993) 357-361
The determination of nine different flavonol glycosides from Tilia using reversed-phase high-performance liquid chromatography (HPLC) and micellar electrokinetic chromatography (MEKC) is described. The analytes were monitored by on-line diode-array UV detection to identify peaks as quercetin or kaempferol derivatives. MEKC is confirmed as a useful complementary technique to HPLC.
Publication DOI: 10.1016/0021-9673(93)83449-3Journal NLM ID: 9318488Publisher: Amsterdam; New York: Elsevier
Institutions: Università degli Studi di Milano, Milan, Italy, ITBA-CNR, Milan, Italy
Methods: HPLC, UV, hydrolysis, MEKC
- Article ID: 10744
Ofman DJ, Markham KR, Vilain C, Molloy BPJ "Flavonoid profiles of New Zealand kauri and other species of Agathis" -
Phytochemistry 38 (1995) 1223-1228
This paper describes the flavonoid constituents in Agathis australis from a wide geographic range and completes a comprehensive survey of the flavonoid chemistry/chemotaxonomy of New Zealand conifers begun in 1984. Flavonol 3-O-glycosides and biflavones of the cupressuflavone and agathisflavone types are shown to be the predominant flavonoids. NMR data for these biflavones with varying degrees of methylation are presented for the first time. The flavonoid profiles of A. australis and three other species of Agathis show a high level of uniformity, and in this respect are closely related.
chemotaxonomy, flavonoids, Agathis australis, Araucariaceae, biflavonoids, cupressuflavone, agathisflavone
Publication DOI: 10.1016/0031-9422(94)00783-PJournal NLM ID: 0151434Publisher: Elsevier
Institutions: New Zealand Institute for Industrial Research and Development, Lower Hutt, New Zealand, Manaaki Whenua-Landcare Research, Lincoln, New Zealand
Methods: 13C NMR, 1H NMR, TLC, LSI-MS, UV, 2D-PC
- Article ID: 10919
Li Y, Liu Y "Flavonol glycosides from Epimedium wushanense" -
Phytochemistry 29 (1990) 3311-3314
A novel flavonol glycoside was isolated from the aerial parts of Epimedium wushanense along with nine known flavonols; icariin, baohuoside-VI, rouhuoside, quercetin 3-galactoside and 3-rhamnoside, epimedoside-A, icaritin, baohuoside-I and baohuoside-II. Their structures were established by spectroscopic methods. The new compound was elucidated as 8-prenylkaempferol-4′-methylether-3-[xylosyl(1→4)rhamnoside]-7-glucoside.
13C, FABMS, 5, 3, 1H NMR, Berberidaceae, Epimedium wushanense, 7-trihydroxy-4′-methoxy-8-prenylflavone-3-[xylosyl(1→4)rhamnoside]-7-glucoside, prenylated flavonol glycosides
Publication DOI: 10.1016/0031-9422(90)80206-VJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Phytochemistry, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Haidian District, Dong Beiwang, Beijing, China
Methods: 13C NMR, 1H NMR, IR, FAB-MS, acid hydrolysis, UV, enzymatic digestion, MPLC
- Article ID: 10944
Ho LK, Lin WN "Quercetin 5,4'-dimethyl ether from Rhododendron ellipticum" -
Phytochemistry 39 (1995) 463-464
From the leaf of Rhodedrndron ellipticum β-carotene, sitosterol, uvaol, quercetin, myricetin, quercitrin, myricitrin, hyperin, quercetin 3-glucoside, and the new aglycone quercetin 5,4′-dimethyl ether were characterized by spectroscopic analysis and/or comparison with authentic samples.
quercetin, Rhododendron ellipticum, qricaceae, myricetin, quercitrin, myricitrin, hyperin, quercetin 3-glucoside, quercetin 5, 4′-dimethyl ether
Publication DOI: 10.1016/0031-9422(94)00905-9Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Pharmacology, National Yang-Ming University, Taipei, Taiwan, R.O.C., Institute of Chinese Medicine, China Medical College, Taichung, Taiwan, R.O.C.
Methods: 13C NMR, 1H NMR, EI-MS, IR, TLC, CC
- Article ID: 10945
Xiong Q, Shi D, Mizuno M "Flavonol glucosides in pericarps of Zanthoxylum bungeanum" -
Phytochemistry 39 (1995) 723-725
Two new flavonol glucosides, viz. quarcetin 3′,4′-dimethyl ether 7-glucoside and tamarixetin 3,7-bis-glucoside, together with hyperin, quercetin, quercitrin, foeniculin, isorhamnetin 7-glucoside, rutin, 3,5,6-trihydroxy-7,4′-dimethoxyflavone, arbutin, sitosterol β-glucoside, l-sesamin and palmitic acid were isolated from the pericarps of Zanthoxylum bungeanum. Their structures were established by spectroscopic and spectrophotometric methods.
pericarp, Zanthoxylum bungeanum, flavonol glycosides, Rutaceae, quercetin 3′, 4′-dimethyl ether 7-glucoside, tamarixetin 3, 7-bis-glucoside
Publication DOI: 10.1016/0031-9422(94)00965-VJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Pharmacognosy, Gifu Pharmaceutical University, Gifu, Japan, Department of Pharmacognosy, School of Pharmacy, Shanghai Medical University, Shanghai, China
Methods: 13C NMR, 1H NMR, UV, CC
- Article ID: 11090
Zhong XN, Otsuka H, Ide T, Hirata E, Takushi A, Takeda Y "Three flavonol glycosides from leaves of Myrsine seguinii" -
Phytochemistry 46(5) (1997) 943-946
From the leaves of Myrsine seguinii, five flavonol glycosides were isolated. Two were identified as quercitrin and myricitrin, and the structures of the remaining three are quercetin 3-rhamnoside-3'-glucoside,myricetin 3-rhamnoside-3'-glucoside, and myricetin 3,4'-dirhamnoside.
flavonol glycosides, quercitrin, myricitrin, Myrsine seguinii, Rapanea neriifolia, Myrsinaceae
Publication DOI: 10.1016/S0031-9422(97)00366-XJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, l-2-3 Kasumi, Minami-ku, Hiroshtma 734, Japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, extraction
- Article ID: 11130
Hasrat JA, Pieters L, Claeys M "Adenosine-1 active ligands: Cirsimarin, a flavone glycoside from Microtea debilis" -
Journal of Natural Products 60(6) (1997) 638-641
Several plants collected through different approaches were screened on distinct receptors using ligand-binding studies as bioassay. Extracts of Microtea debilis showed high activity on adenosine A(1) receptors. Bioassay-guided fractionation using ligand-binding studies resulted in the isolation of an adenosine A(1) active ligand, cirsimarin (cirsimaritin 4'-O-glucoside). GTP did not influence the radioligand inhibition curve of cirsimarin, indicating that this compound is acting as an antagonist at the adenosine-A(1) receptors. The use of this plant against ''proteinuria'' in traditional medicine in Suriname (South America) may be explained by the adenosine A(1) antagonistic action of cirsimarin. A series of flavonoids was tested in the same assay, but they were less active. No structure-activity relationship could be observed.
NCBI PubMed ID: 9214739Publication DOI: 10.1021/np970025kJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Institutions: Department of Pharmaceutical Sciences, University of Antwerp, Universiteitsplein 1, B-2610, Antwerp, Belgium
Methods: 13C NMR, 1H NMR, FAB-MS, TLC, acid hydrolysis, biological assays, UV, extraction
- Article ID: 11131
Shirasuna K, Miyakoshi M, Mimoto S, Isoda S, Satoh Y, Hirai Y, Ida Y, Shoji J "Lupane triterpenoid glycosyl esters from leaves of Acanthopanax divaricatus" -
Phytochemistry 45(3) (1997) 579-584
Further investigation of the leaves of Acanthopanax divaricatus gave two analogues of chiisanoside, which is a lupane triterpenoid oligoglycosyl ester. The structures were established as 28-O-α-l-rhamnopyranosyl(1→4)-β-d-glucopyranosyl(1→6)β-d-glucopyranosyl esters of 1β,11α-dihydroxy-3-oxo-lup-20(29)-en-28-oic acid and 1(R),11α,22α-trihydroxy-3,4-seco-lupa-4(23),20(29)-diene-3,28-dioic acid 3,11α-lactone based on chemical and spectroscopic evidence. in biosynthetic terms, one is the precursor of chiisanoside and the other is an oxygenated derivative chiisanoside.
araliaceae, triterpenoid saponin, Acanthopanax divaricatus, lupane glycoside, chiisanoside, isochiisanoside, protochiisanoside, 22α-hydroxychiisanoside
Publication DOI: 10.1016/S0031-9422(97)00017-4Journal NLM ID: 0151434Publisher: Elsevier
Institutions: School of Pharmaceutical Sciences, Showa University, Hatamodai 1-5-8, Shinagawa-ku Tokyo 142, Japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, sugar analysis, TLC, enzymatic hydrolysis, acid hydrolysis, GC, chemical methods, extraction
- Article ID: 11161
Arot LOM, Williams LAD "A flavonol glycoside from Embelia schimperi leaves" -
Phytochemistry 44(7) (1997) 1397-1398
A new flavonol glycoside, quercetin 3-galactosyl(1→2)rhamnoside, has been isolated from the leaves of Embelia schimperi. The known compounds quercetin 3-rutinoside, quercetin 3-rhamnoside, quercetin 3-galactoside, myricetin and quercetin were also identified from this plant.
structural elucidation, Myrsinaceae, Embelia schimperi, quercetin 3-galactosyl(1→2)rhamnoside
Publication DOI: 10.1016/S0031-9422(96)00706-6Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Kenya Forestry Research Institute, Non-Timber Forest Products Research, Nairobi, Kenya
Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, sugar analysis, TLC, acid hydrolysis, chemical methods, UV, extraction, RP
- Article ID: 11313
de Almeida AP, Miranda MMFS, Simoni IC, Wigg MD, Lagrota MHC, Costa SS "Flavonol monoglycosides isolated from the antiviral fractions of Persea americana (Lauraceae) leaf infusion" -
Phytotherapy Research 12(8) (1998) 562-567
An infusion of Persea americana leaves (Lauraceae) strongly inhibited herpes simplex virus type 1 (HSV-1), Aujeszky's disease virus (ADV) and adeno virus type 3 (AD3) in cell cultures. Its fractionation, guided by anti-HSV-1 and ADV assays, allowed the isolation and identification of two new flavonol monoglycosides, kaempferol and quercetin 3-O-alpha-D-arabinopyranosides, along with the known kaempferol 3-O-alpha-L-rhamnopyranoside (afzelin), quercetin 3-O-alpha-L-rhamnopyranoside (quercitrin), quercetin 3-O-beta-glucopyranoside and quercetin, The known quercetin 3-O-beta-galactopyranoside was identified in a mixture. Afzelin and quercetin 3-O-alpha-D-arabinopyranoside showed higher activity against acyclovir-resistant HSV-I, Chlorogenic add significantly inhibited the HSV-1 replication without any cytotoxicity. However, all the substances tested were less active than the infusion or fractions. The same substances did not affect ADV replication. Chemical structures were elucidated by the analysis of UV, H-1 and C-13 NMR data, mainly by APT, homo and heteronuclear COSY experiments. The configuration of the D-arabinose unit, not usual in natural plant products, was established on the basis of the optical rotation of the free sugar obtained after acid hydrolysis.
quercetin, leaves, quercitrin, Persea americana, kaempferol 3-o-alpha-d-arabinopyranoside, quercetin 3-o-alpha-d-arabinopyranoside, afzelin, quercetin 3-o-beta-glucopyranoside, quercetin 3-o-beta-galactopyranoside, chlorogenic acid, herpes simplex virus type 1, aujeszky's disease virus, adenovirus type 3
Publication DOI: 10.1002/(SICI)1099-1573(199812)12:8<562::AID-PTR356>3.0.CO;2-6Journal NLM ID: 8904486Publisher: Chichester: Wiley
Institutions: Núcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil, Instituto de Microbiologia, Departamento de Virologia, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil, Instituto Biológico de São Paulo, Seção de Biologia Celular, São Paulo, Brazil
Methods: 13C NMR, 1H NMR, TLC, acid hydrolysis, paper chromatography, UV, optical rotation measurement, CC, melting point determination, antiviral assay
- Article ID: 11595
Barakat HH "Chemical investigation of the constitutive phenolics of Ailanthus altissima; The structure of a new flavone glycoside gallate" -
Natural Product Sciences 4(3) (1998) 153-157
The aqueous ethanolic leaf extract of Ailanthus altissima was found to contain the new natural product, luteolin 7-O-β-(6'- galloylglucopyranoside), 13, along with fourteen known phenotic metabolites (1-12, 14 and 15). Structures of all compounds (1-15) were established by conventional methods of analysis and confirmed by FAB-MS, 1H- and 13C-NMR spectral analysis.
13C-NMR, FAB-MS, phenolics, Simaroubaceae, Ailanthus altissima, luteolin 7-O-β-(6'- galloylglucopyranoside)
Journal NLM ID: 9714997Publisher: Seoul, Korea: Korean Society of Pharmacognosy
Institutions: National Research Centre, Dokki, Cairo, Egypt
Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, UV, extraction, CC
- Article ID: 11700
Cimanga K, De Bruyne T, Hu JP, Cos P, Apers S, Pieters L, Tona L, Van Den Berghe D, Vlietinck AJ "Constituents from Morinda morindoides leaves as inhibitors of xanthine oxidase and scavengers of superoxide anions" -
Pharmacy and Pharmacology Communications 5(6) (1999) 419-424
Morinda morindoides (Kongobololo or Nkongabululu) is one of the most popular medicinal plants used in the Democratic Republic of Congo. Ten of its constituent flavonoids were evaluated in the xanthine-xanthine oxidase enzymatic system. The compounds were identified by spectroscopic methods as quercetin (1), quercetin 7,4' dimethylether (2), luteolin 7 glucoside (3), apigenin 7 glucoside (4), quercetin 3 rhamnoside (5), kaempferol 3 rhamnoside (6), quercetin 3 rutinoside (7), kaempferol 3 rutinoside (8), chrysoeriol 7 neohesperidoside (9) and kaempferol 7 rhamnosylsophoroside (10). The aglycones chrysoeriol (11), kaempferol (12), luteolin (13) and apigenin (14), obtained by acid hydrolysis of the corresponding glycosides, were also included. Compound 5 exhibited only scavenging activity, 9 and 11 were devoid of any effect against xanthine oxidase and scavenging activity, and the remaining flavonoids exhibited xanthine oxidase inhibiting and superoxide scavenging activity to varying extent. Study of structure activity relationships demonstrated that the activity was not only dependent on the nature of substituents and the substitution site, but also on the nature of the aglycone. These results partially explain and support the use of Morinda morindoides in the treatment of rheumatism.
flavonoid glycoside, Morinda morindoides, xanthine oxidase inhibition, superoxide anion scavanger
Publication DOI: 10.1211/146080899128735009Journal NLM ID: 9807134Publisher: London: Pharmaceutical Press
Institutions: Department of Pharmaceutical Sciences, University of Antwerp, Universiteitsplein 1, B 2610, Wilrijk, Antwerp, Belgium, Faculty of Pharmacy, University of Kinshasa, B.P. 212, Kinshasa XI, Congo
Methods: statistical analysis, antioxidant activities
- Article ID: 11799
Felser C, Schimmer O "Flavonoid glycosides from Alchemilla speciosa" -
Planta Medica 65(7) (1999) 668-670
The new flavonol glycosides quercetin 3-O-β-(2-O-α-L-rhamnopyranosyl)-glucopyranoside uronic acid and kaempferol 3-O-β-(2-O-α-L-rhamnopyranosyl)-glucopyranoside uronic acid were isolated from the leaves of Alchemilla speciosa Buser together with 13 known flavonol and flavone glycosides and (+)-catechin. The structures were determined by spectroscopic methods.
flavonol glycosides, Alchemilla speciosa, spectroscopic methods
NCBI PubMed ID: 17260291Publication DOI: 10.1055/s-2006-960845Journal NLM ID: 0066751Publisher: George Thieme
Institutions: Institut für Botanik und Pharmazeutische Biologie, Lehrstuhl Pharmazeutische Biologie, Universität Erlangen-Nürnberg, Erlangen, Germany
Methods: 13C NMR, 1H NMR, methylation, TLC, HPLC, UV, acetylation, HCl hydrolysis
- Article ID: 12005
Ashida H, Fukuda I, Yamashita T, Kanazawa K "Flavones and flavonols at dietary levels inhibit a transformation of aryl hydrocarbon receptor induced by dioxin" -
FEBS Letters 476(3) (2000) 213-217
Dioxins invade the body mainly through the diet, and produce toxicity through the transformation of aryl hydrocarbon receptor (AhR). An inhibitor of the transformation should therefore protect against the toxicity and ideally be part of the diet. We examined flavonoids ubiquitously expressed in plant foods as one of the best candidates, and found that the subclasses flavones and flavonols suppressed antagonistically the transformation of AhR induced by 1 nM of 2,3,7,8-tetrachlorodibenzo-p-dioxin, without exhibiting agonistic effects that transform AhR. The antagonistic IC(50) values ranged from 0.14 to 10 μM, close to the physiological levels in human.
flavonoid, cancer prevention, dioxin antagonist, aryl hydrocarbon receptor, transformation inhibitor, dietary phytochemical
NCBI PubMed ID: 10913616Publication DOI: 10.1016/s0014-5793(00)01730-0Journal NLM ID: 0155157Publisher: Elsevier
Correspondence: Kanazawa K
Institutions: Laboratory of Food and Nutritional Chemistry, Faculty of Agriculture, Kobe University, Kobe, Japan
Methods: DNA techniques, biological assays, radiolabeling, centrifugation, autoradiography
- Article ID: 12009
Awad MA, de Jager A "Flavonoid and chlorogenic acid concentrations in skin of ‘Jonagold’ and ‘Elstar’ apples during and after regular and ultra low oxygen storage" -
Postharvest Biology and Technology 20(1) (2000) 15-24
Apples are important dietary sources of potentially healthy phenolics. In three successive seasons, the changes in concentrations of flavonoids and chlorogenic acid in the skin of two apple cultivars ‘Jonagold’ and ‘Elstar’ during and after regular (RS) and ultra low oxygen storage (ULO) at 1°C, were quantified by reversed-phase high performance liquid chromatography (RP-HPLC) with UV-VIS detector. There were no significant differences in the concentrations of flavonoids and chlorogenic acid between fruits stored under ULO and RS conditions. During storage of both ‘Jonagold’ (3, 6 and 8 months) and of ‘Elstar’ (2, 4 and 6 months), and during 1 or 2 weeks shelf life, the concentrations of cyanidin 3-galactoside and quercetin glycosides were relatively constant, while the concentrations of catechins, phloridzin and chlorogenic acid showed only minor changes. Exposing ‘Jonagold’ and ‘Elstar apples’ to white light during shelf life following storage increased the concentration of cyanidin 3-galactoside but not any of the other flavonoid classes. An explanation for this might be that the synthesis of different flavonoid classes may have different spectral sensitivity characteristics. It is concluded that flavonoids present in apples are stable and possibly not subject to net metabolic turnover during storage and shelf life.
phenolics, flavonoids, chlorogenic acid, storage condition, storage duration, quality
Publication DOI: 10.1016/S0925-5214(00)00116-2Journal NLM ID: 9884964Publisher: Amsterdam; New York: Elsevier
Correspondence: a.de.jager@fpo.agro.nl
Institutions: Fruit Research Station, Zetten, The Netherlands
Methods: UV, extraction, RP-HPLC, spectrophotometry
- Article ID: 12011
Awad MA, de Jager A, van Westing LM "Flavonoid and chlorogenic acid levels in apple fruit: characterisation of variation" -
Scientia Horticulturae 83(3-4) (2000) 249-263
Variations in flavonoid and chlorogenic acid levels within fruit, within tree, between orchards, between cultivars and among mutants were characterised and quantified in ‘Elstar’ and ‘Jonagold’ apples by reversed-phase high performance liquid chromatography (RP-HPLC). The sun-exposed skin of individual fruit had much higher cyanidin 3-galactoside (anthocyanin) and quercetin 3-glycoside levels than the shaded skin, while phloridzin, catechins and chlorogenic acid were similar in the skin of both sides. Individual flavonoid and chlorogenic acid levels were not equally distributed within the fruit. Quercetin 3-glycosides and anthocyanin were almost exclusively found in the skin. Catechins were mostly found in the skin but some were present in the flesh. Phloridzin was most abundant in the seeds, with intermediate levels in both the core area and the skin, and the lowest level in the flesh. Chlorogenic acid was mainly present in the core area and the seeds with an intermediate level in the flesh and a low level in the skin. The levels of anthocyanin, quercetin 3-glycosides and total flavonoids were highest in fruit borne in the top of the tree followed by fruit from the outer tree parts, whereas the lowest levels were found in fruit from the inner tree. Terminal fruit contained the highest levels of these compounds, including catechins, compared to lateral and spur fruit. Phloridzin and chlorogenic acid were not affected by the position of the fruit in the tree nor by the bearing wood type. There were large differences in flavonoid and chlorogenic acid levels in ‘Elstar’ fruit between two normally productive orchards differing mainly in growth vigour. ‘Jonagold’ and its mutants had considerably higher levels of flavonoid and chlorogenic acid than ‘Elstar’ and its mutants. The most blushed mutants of both cultivars had higher levels of anthocyanin but not of flavonoids or chlorogenic acid compared to the standard cultivar and to the less blushed mutants. The most blushed mutants had a higher number of red cells per cell layer and more cell layers containing red cells than the standard cultivar and the less blushed mutants.
variation, flavonoids, apple, anthocyanin, chlorogenic acid
Publication DOI: 10.1016/S0304-4238(99)00124-7Journal NLM ID: 9882883Publisher: Amsterdam, International Society for Horticultural Science
Correspondence: a.de.jager@fpo.agro.nl
Institutions: Fruit Research Station, Randwijk, The Netherlands
Methods: UV, extraction, microscopy, RP-HPLC, spectrophotometry, sonication
- Article ID: 12064
Chang Y-C, Chang F-R, Wu Y-C "The constituents of Lindera glauca" -
Journal of the Chinese Chemical Society = Zhongguo hua hsueh hui hui zhi 47(2) (2000) 373-380
Twenty-eight compounds including seven alkaloids, (+)-3-chloro-N-formylnornantenine (1), (+)-N-formylnornantenine (2), (+)-boldine (3), (+)-norboldine (4), (-)-norboldine (5), lycicamine (6), and tetrahydroberberine (7); four flavonoids, kaempferol (8), kaempferol-3-O-arabinoside (9), quercetin (10), and quercetin-3-O-rhamnoside (11); one butanolide, akolactone A (12); one p-quinone, 2,6-dimethoxy-p-quinone (13); one cyclohex-2-en-1-one, blumenol A (14); six benzenoids, methylparaben (15), p-hydroxybenzoic acid (16), vanillic acid (17), syringic acid (18), 3,4,5-trimethoxybenzoic acid (19), and 3-(3,4-dihydroxyphenyl) propionic acid (20); one diterpene, phytol (21); one triterpene, squalene (22); six steroids, (3-sitosterol (23), β-sitostenone (24), stigmasta-4,22-dien-3-one (25), 6β-hydroxy-β-sitostenone (26), 6β-hydroxystigmasterone (27), and β-sitosteryl-D-glucoside (28) were isolated from the aerial part of Lindera glauca. These compounds were characterized and identified by physical and spectral method. All compounds were isolated for the first time from this plant. Among them, (+)-3-chloro-N-formylnornantenine (1) is a new one.
Lindera glauca
Publication DOI: 10.1002/jccs.200000050Journal NLM ID: 16210600RPublisher: Taipei: Chinese Chemical Society
Institutions: Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan, China, Department of Chemical Engineering, Kao Yuan Institute of Technology, Kaohsiung, Taiwan, China
Methods: 13C NMR, 1H NMR, EI-MS, IR, UV, extraction, optical rotation measurement, CC, melting point determination, evaporation, PTLC
- Article ID: 12149
DuPont MS, Mondin Z, Williamson G, Price KR "Effect of variety, processing, and storage on the flavonoid glycoside content and composition of lettuce and endive" -
Journal of Agricultural and Food Chemistry 48(9) (2000) 3957-3964
Eight varieties of lettuce (Lactuca sativum) and three varieties of endive (Cichorium endivia) were analyzed for flavonoid composition and content. Total flavonoid contents, expressed as units of aglycon for fresh material, were in the ranges of 0.3-229 μg/g for lettuce and 44-248 μg/g for endive. Five quercetin conjugates [quercetin 3-O-galactoside, quercetin 3-O-glucoside, quercetin 3-O-glucuronide, quercetin 3-O-(6-O-malonyl)glucoside, and quercetin 3-O-rhamnoside] and luteolin 7-O-glucuronide were measured in the green-leafed lettuce and an additional two cyanidin conjugates [cyanidin 3-O-glucoside and cyanidin 3-O-[(6-O-malonyl)glucoside]] in the red-leafed varieties. Three kaempferol conjugates [kaempferol 3-O-glucoside, kaempferol 3-O-glucuronide, and kaempferol 3-O-[6-O-malonyl)glucoside]] were measured in each of the endive varieties. The presence and identity of kaempferol 3-O-(6-O-malonyl)glucoside in endive was shown for the first time. Shredding of lettuce leaf followed by exposure to light produced significant losses of the flavonoid moiety in the green oak leaf (94%), red oak leaf (43%), iceberg (36%), green batavia (25%), lollo biondo (24%), and lollo rosso (6%) samples, whereas cos and green salad bowl samples did not show an overall loss. Shredding of endive also produced loss of the flavonoid moiety in escarole (32%), fine frisee (13%), and coarse frisee (8%). Significant demalonation was observed for both the quercetin and cyanidin glucosides in lettuce, whereas a similar degradation of the kaempferol analogue was found in endive tissue. Storage of whole heads of both lettuce and endive in the dark at 1 degrees C and 98% humidity for 7 days resulted in losses of total flavonol glycosides in the range of 7-46%. The identification of the amounts, position of substitution, and nature of the sugars is important for understanding the potential bioavailability and biological activities of flavonoids in salads.
HPLC, lettuce, flavonoid, endive, flavonoid conjugates
NCBI PubMed ID: 10995297Publication DOI: 10.1021/jf0002387Journal NLM ID: 0374755Publisher: American Chemical Society
Institutions: Diet, Health and Consumer Science Division, Institute of Food Research, Norwich Research Park, Norwich, UK
Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, HPLC, enzymatic digestion, extraction, CC, evaporation, APCI-MS
- Article ID: 12242
Hollman PCH, Arts ICW "Flavonols, flavones and flavanols – nature, occurrence and dietary burden" -
Journal of the Science of Food and Agriculture 80(7) (2000) 1081-1093
Total flavonol and flavone contents of foods have been determined with validated state-of-the-art methods. Quercetin dominates, and flavonol levels found in vegetables and fruits are below 10 mg kg−1. However, high concentrations are found in onions (300 mg/kg), kale (450 mg/kg), broccoli (100 mg/kg), beans (50 mg/kg), apples (50 mg/kg), blackcurrants (40 mg/kg), and tea (30 mg/l). The dietary intake of flavonols varies 10-fold between countries (6–60 mg/day). Flavones are of minor importance in the diet. Tea, wine and fruits are the most important sources of flavanols, but there are gaps in our knowledge on flavanol levels of many foods. The absorption of dietary quercetin glycosides in humans ranges from 20 to 50%. The sugar moiety is an important determinant of the bioavailability of flavonols. The presence of a glucose moiety significantly enhances absorption. The extent of absorption of flavanols in humans seems similar to that of flavonols but has been little studied. Flavonols and flavanols are extensively metabolised, as only 1–2% of them are excreted with an intact flavonoid backbone. Hepatic biotransformations include glucuronidation and sulphatation of the phenolic hydroxyls and O-methylation of catechol groups. Bacteria of the colon cleave the C-ring of the flavonoid nucleus to phenolic acids which are subsequently absorbed. Apart from conjugates, virtually no metabolites have been characterised in humans. Absorption of flavanols is rather fast, with times to reach peak values between 0.5 and 4 h. Flavanols are rapidly excreted, with elimination half-lives of 1–6 h. Quercetin glycosides show rapid to slow absorption; peak values are reached between < 0.5 and 9 h. The type of glycoside determines the rate of absorption. Excretion of quercetin glycosides is slow: elimination half-lives are 24 h, independent of the type of glycoside. Analytical data for flavanols in foods are needed. Tea, as an important dietary source, has to be studied. Research on the bioavailability of flavonols and flavanols has to be expanded. Attention is needed for the identification and quantification of their metabolites in body fluids.
glycosides, bioavailability, flavones, flavonols, catechins, flavanols, food contents, dietary intake, absorption metabolism, phenolic acids
Publication DOI: 10.1002/(SICI)1097-0010(20000515)80:7<1081::AID-JSFA566>3.0.CO;2-GJournal NLM ID: 0376334Publisher: Chichester, West Sussex: John Wiley And Sons Ltd
Institutions: National Institute of Public Health and the Environment, Bilthoven, The Netherlands, State Institute for Quality Control of Agricultural Products (RIKILT), Wageningen, The Netherlands
- Article ID: 12246
Hou AJ, Peng LY, Liu YZ, Lin ZW, Sun HD "Gallotannins and related polyphenols from Pistacia weinmannifolia" -
Planta Medica 66(7) (2000) 624-626
Two new gallotannins, pistafolins A (1) and B (2), were isolated from the leaf extract of Pistacia weinmannifolia. Their structures were determined by spectral methods. Four known gallotannins (3 - 6), seven known flavonoid glycosides (7 - 13), along with 1-O-β-D-(6′-O-galloyl)-glucopyranosyl-3-methoxy-5-hydroxybenzene (14), gallic acid (15), methyl gallate (16), (+)-catechin (17), and (+)-gallocatechin (18), were also isolated. Some of these compounds were tested for their cytotoxicity toward K562 cells, and two small molecular phenolic compounds, 15 and 18, showed significant inhibitory effects with IC50 values less than 5 μg/ml.
cytotoxicity, B, polyphenols, Anacardiaceae, Pistacia weinmannifolia, gallotannin, pistafolins A
NCBI PubMed ID: 11105566Publication DOI: 10.1055/s-2000-8633Journal NLM ID: 0066751Publisher: George Thieme
Correspondence: hdsun@mail.kib.ac.cn
Institutions: Laboratory of Phytochemistry, Kunming Institute of Botany, Academia Sinica, Kunming, China, Department of Phytochemistry, Henan College of Traditional Chinese Medicine, Zhengzhou, China
Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS, UV, extraction, optical rotation measurement, CC, cytotoxicity assay, evaporation, HR-FAB-MS
- Article ID: 12263
Kang TH, Jeong SJ, Kim NY, Higuchi R, Kim YC "Sedative activity of two flavonol glycosides isolated from the flowers of Albizzia julibrissin Durazz" -
Journal of Ethnopharmacology 71(1-2) (2000) 321-323
The flowers of Albizzia julibrissin are used as a sedative in oriental traditional medicine. The phytochemical study of this plant allowed the isolation of two flavonol glycosides, quercitrin (1) and isoquercitrin (2). The sedative activity of these compounds was evaluated, and both compounds 1 and 2 increased pentobarbital-induced sleeping time in dose-dependent manner in mice. These results support the use of the flowers of this plant as a sedative agent.
flavonoids, Leguminosae, Albizzia julibrissin, sedative activity
NCBI PubMed ID: 10904180Publication DOI: 10.1016/s0378-8741(99)00202-0Journal NLM ID: 7903310Publisher: Limerick: Elsevier Sequoia
Correspondence: yckim@wonnms.wonkwang.ac.kr
Institutions: Faculty of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan, College of Pharmacy, Wonkwang University, Iksan, South Korea
Methods: 13C NMR, 1H NMR, biological assays, UV, extraction, CC, melting point determination
- Article ID: 12269
Kawanishi K, Farnsworth NR "Current status of the chemistry and synthesis of natural antimalarial compounds and natural substances used to alleviate symptoms of diabetes (aldose reductase and α-glucosidase inhibitors)" -
Book: Studies in Natural Products Chemistry (series: Bioactive Natural Products) (2000) Vol. 22, Chapter C, 145-192
Atropine, camptothecin, cocaine, digitoxin, digoxin, morphine, pilocarpine, quinine, taxol, vinblastine and vincristine, among others, are important drugs obtained from higher plants and are used clinically. They have also served as lead compounds for the synthesis and modification of more effective and safer drugs, in many cases. In this chapter, drugs used as antimalarial compounds and for the complications of diabetes (aldose reductase and α-glucosidase inhibitors) will be discussed. Natural product chemists have isolated as little as 1.0 mg of pure compounds from natural sources and have been able to determine their structures using high resolution instrumental techniques. Organic chemists have synthesized thousands of compounds to produce one new drug on the basis of natural product leads, and pharmacologists and biochemists have tested their biological activity. Recently chemists and pharmacologists have worked together to develop techniques for studying structure-activity relationships using computer graphics and have designed new drugs. Biochemists, molecular biologists and pharmacologists have identified many receptors on which drugs act. Thus, mechanisms of drug action at the molecular level are being identified. From the accumulation of these results structure-activity relationships will lead to the preparation of thousands of useful compounds. We must produce drugs in these ways, because we cannot rely on solely on the limited amount of active compounds produced naturally in plants, in many cases, for a number of reasons. However we need to employ plant extracts themselves, because there are millions of people who cannot buy expensive synthetic drugs in the world and these extracts are widely used by them.
Publication DOI: 10.1016/S1572-5995(00)80025-3Publisher: New York: Elsevier
Editors: Atta-ur-Rahman
Institutions: Kobe Pharmaceutical University, Kobe, Japan, Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA
- Article ID: 12282
Kim M-H, Park JH, Park C-W "Flavonoid chemistry of Fallopia section Fallopia (Polygonaceae)" -
Biochemical Systematics and Ecology 28(5) (2000) 433-441
Five controversial species of Fallopia sect. Fallopia sensu Holub were examined for leaf flavonoid constituents. Twenty-one flavonoid compounds were isolated and identified; they were glycosylated derivatives of the flavonols kaempferol, quercetin, and myricetin, and of the flavones apigenin and luteolin. Among them, quercetin 3-O-galactoside and quercetin 3-O-glucoside were major flavonoid constituents and present in all species. Although the flavonoid data for some species are lacking, those available appear to be useful for species delimitation and for recognizing species relationships in the section. The flavonoid data, in conjunction with morphological evidence, strongly suggest that F. scandens, F. dentatoalata, F. dumetorum, and F. convolvulus are closely allied but distinct species. In addition, the flavonoid data for F. cilinodis lend additional support to the segregation of sect. Parogonum from sect. Fallopia.
chemotaxonomy, Polygonaceae, Fallopia sect. Fallopia, sect. Parogonum, leaf flavonoids
NCBI PubMed ID: 10725600Publication DOI: 10.1016/s0305-1978(99)00084-8Journal NLM ID: 0430442Publisher: Pergamon Press
Correspondence: Park C-W
Institutions: Department of Biology, College of Natural Sciences, Seoul National University, Seoul, South Korea
Methods: TLC, acid hydrolysis, paper chromatography, HPLC, alkaline hydrolysis, UV, enzymatic digestion, extraction, oxidation
- Article ID: 12320
Kruthiventi AK, Krishnaswamy NR "Constituents of the flowers of Persea gratissima" -
Fitoterapia 71(1) (2000) 94-96
The flowers of Persea gratissima yielded an acylated flavonol 3-O-trans-p-coumaroylkaempferol (1), in addition to quercetin 3-O-rhamnoside (2) and isorhamnetin 3-O-glucoside (3).
flavonoids, Persea gratissima
NCBI PubMed ID: 11449484Publication DOI: 10.1016/s0367-326x(99)00125-2Journal NLM ID: 16930290RPublisher: Elsevier
Institutions: Department of Chemistry, Sri Satya Sai Institute of Higher Learning, Prashantinilayam, India
- Article ID: 12333
Laitinen M-L, Julkunen-Tiitto R, Rousi M "Variation in phenolic compounds within a birch (Betula pendula) population" -
Journal of Chemical Ecology 26(7) (2000) 1609-1622
In previous studies, the qualitative and quantitative variation found in defense chemistry among birch populations and even among individual clones has been considerable. However, information about variation among adult, naturally regenerated birch trees from natural populations is still lacking. In this study, the phenolic composition of leaves of 30 naturally regenerated 20-year-old birch (Betula pendula) trees was analyzed for two successive years in order to characterize the chemical composition of individual trees, analyze the annual variation, and determine chemical similarities among individual trees within a population. The main phenolic compounds were flavonoid glycosides, myricetin, and quercetin derivatives. Annual variation in concentration among leaves was large. In most trees, concentrations were markedly higher in 1998 than in 1997; for certain compounds, the detected increase was as much as a 50%. However, for some individual trees, there were no differences between years in chemical quantity. Thus, when selection or grouping of trees is based on secondary chemistry, quantitative variation should be considered carefully. With the qualitative UPGMA method of classification, four chemotypes were found. The grouping was similar for both years, and qualitatively the results of an individual tree seem to be independent of sampling year. The stability in chemical profile of individual trees suggests that quality is tightly controlled by genotype, which provides a recognition tool for chemotaxonomy. The high within-population variation found in leaf defense chemistry may provide protection against different types of insects (generalists or specialists) and, thus, have positive effects on population survival.
variation, population, chemotype, phenolic compounds, birch, Betulaceae, Betula pendula
Publication DOI: 10.1023/A:1005582611863Journal NLM ID: 7505563Publisher: Springer
Correspondence: mllaitin@cc.joensuu.fi
Institutions: Finnish Forest Research Institute, Punkaharju Research Station, Punkaharju, Finland, Department of Biology, University of Joensuu, Joensuu, Finland
- Article ID: 12334
Lamba SS, Buch KY, Lewis III H, Lamba J "Phytochemicals as potential hypoglycemic agents" -
Book: Studies in Natural Products Chemistry (series: Bioactive Natural Products) (2000) Vol. 21, Chapter B, 457-496
Diabetes mellitus is a chronic metabolic disorder characterized by a high blood glucose concentration (hyperglycemia) which is due to insulin deficiency and/or insulin resistance. Hyperglycemia occurs because the liver and skeletal muscle cannot store glycogen and the tissues are unable to take up and utilize glucose. Treatment of diabetes is afforded by the following: (i) diet and exercise, (ii) insulin replacement therapy and (iii) the use of oral hypoglycemic agents. In folklore, a variety of plant extracts have been used to treat diabetic patients for centuries. Folklore has given the field of medicine many useful drugs, such pharmacologic prototypes include Digitalis(digitoxin, digoxin), Atropa, Hyoscyamnsand Datura(atropine, scopolamine), Catharanthus(vincristine, vinblastine), Erythroxylon(cocaine), Claviceps(ergonovine, ergotamine), Papaver(morphine, codeine and papaverine), Pilocarpus(pilocarpine) Rauvolfia(reserpine, rescinnamine, deserpidine), and Cinchona(quinine, quinidine); and many others. Obviously evaluation of plants and their active constituents has proven a very useful way of obtaining several useful therapeutic agents. Hence, a logical review of plant constituents having hypoglycemic activity could provide useful clues for obtaining new hypoglycemic agents. Plant constituents reportedly possessing hypoglycemic activity can be classified as follows: 1. Alkaloids; 2. Flavonoids and related compounds; 3. Glycosides/Steroids/Terpenoids; 4. Polysaccharides/ Proteins; and 5. Miscellaneous compounds. Phytoconstituents based upon the above classification are discussed including selected names of plants which are listed alphabetically according to genus. Appropriate data on their pharmacological activity, mechanisms of action (where applicable), and other relevant properties are discussed.
diabetes mellitus, hypoglycemic activity, natural drugs
Publication DOI: 10.1016/S1572-5995(00)80012-5Publisher: New York: Elsevier
Editors: Atta-ur-Rahman
Institutions: Florida A & M University, College of Pharmacy and Pharmaceutical Sciences, Tallahassee, USA, Parke-Davis, Division of Warner-Lambert Company, Morris Plain, USA
- Article ID: 12379
Ivancheva S, Petrova A "A chemosystematic study of eleven Geranium species" -
Biochemical Systematics and Ecology 28(3) (2000) 255-260
The flavonoids of 11 species from six sections (Geranium, Batrachioides, Lucida, Unguiculata, Robertium, Erodioideae) of the genus Geranium have been studied. Quercetin and its derivatives were the most common aglycones with lesser amounts of kaempferol, myricetin and luteolin. Glycosylation was found mainly in the 3 or 4′ positions and to a lesser extent in the 7 position. Chemosystematic relationships are discussed. The occurrence of exudate flavonoids various methyl ether of kaempferol, quercetin and myricetin has been detected in all the 11 species surveyed.
flavonoid glycosides, chemosystematics, Geranium, flavonoid aglycones
Publication DOI: 10.1016/S0305-1978(99)00060-5Journal NLM ID: 0430442Publisher: Pergamon Press
Correspondence: Ivancheva S
Institutions: Institute of Botany, Bulgarian Academy of Sciences, Sofia, Bulgaria
Methods: TLC, extraction, CC, evaporation
- Article ID: 12401
Lin L-C, Kuo Y-C, Chou C-J "Anti-herpes simplex virus type-1 flavonoids and a new flavanone from the root of Limonium sinense" -
Planta Medica 66(4) (2000) 333-336
From the root of Limonium sinense (Girard) Ktze a new (2R,3S)-3,5,7,4′-tetrahydroxy-3′,5′-dimethoxyflavanone was isolated and named isodihydrosyringetin (3), together with nine other known compounds, (-)-epigallocatechin 3-O-gallate (1), samarangenin B (2), myricetin (4), myricetin 3-O-α-rhamnopyranoside (5), quercetin 3-O-α-rhamnopyranoside (6), (-)-epigallocatechin (7), gallic acid (8), N-trans-caffeoyltyramine (9), and N-trans-feruloyltyramine (10). All of them were examined for their inhibitory effects on herpes simplex virus type-1 (HSV-1) replication in Vero cells. Both compounds 1 and 2 exhibited potent inhibitory activities in HSV-1 replication. Comparison of the IC50 values indicated that compounds 1 and 2 had higher inhibitory activities than the positive control acyclovir (38.6 ± 2.6 vs. 55.4 ± 5.3 μM, P < 0.001; 11.4 ± 0.9 vs. 55.4 ± 5.3 μM, P < 0.0005). Cytotoxicity was unlikely involved because no cell deaths were observable in the Vero cells following 5 day treatments with compound 1 or 2.
inhibition, Limonium sinense, Plumbaginaceae, isodihydrosyringetin, herpes simplex virus type-1
NCBI PubMed ID: 10865449Publication DOI: 10.1055/s-2000-8540Journal NLM ID: 0066751Publisher: George Thieme
Correspondence: lclin@cma23.nricm.edu.tw
Institutions: National Research Institute of Chinese Medicine, Taipei, Taiwan, China
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, acid hydrolysis, biological assays, HPLC, alkaline hydrolysis, extraction, CI-MS, HR-ESI-MS, cytotoxicity assay, evaporation, centrifugation
- Article ID: 12402
Lin L-C, Chou C-J "Flavonoids and phenolics from Limonium sinense" -
Planta Medica 66(4) (2000) 382-383
From the aerial part of Limonium sinense (Girard) Ktze, a new flavonol glycoside, myricetin 3-O-(2″-O-p-hydroxybenzoyl)-α-rhamnopyranoside has been isolated together with known flavonols, flavonol glycosides, flavonol glycoside gallates, flavones, flavanones, flavan-3-ols and gallic acid. The structural determinations of these compounds were based on spectral analyses.
structural determination, phenolics, flavonoid glycosides, Limonium sinense
NCBI PubMed ID: 10865464Publication DOI: 10.1055/s-2000-8547Journal NLM ID: 0066751Publisher: George Thieme
Correspondence: lclin@cma23.nricm.edu.tw
Institutions: National Research Institute of Chinese Medicine, Taipei, Taiwan, China
Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, TLC, HPLC, extraction, evaporation, centrifugation, HR-EI-MS
- Article ID: 12412
Liu FF, Ang CYW, Heinze TM, Rankin JD, Beger RD, Freeman JP, Lay JO Jr "Evaluation of major active components in St. John’s Wort dietary supplements by high-performance liquid chromatography with photodiode array detection and electrospray mass spectrometric confirmation" -
Journal of Chromatography A 888(1-2) (2000) 85-92
A RP-HPLC method with photodiode array detection and LC–electrospray ionization (ESI) MS confirmation was established for the determination of major active components in St. John’s Wort dietary supplement capsules. The samples alternatively were extracted with ethanol–acetone (2:3) using a 55°C water-bath shaker or an ambient temperature ultrasonic bath. Extracts were separated by RP-C18 chromatography using a 95-min water–methanol–acetonitrile–trifluoroacetic acid gradient. The major components were identified by photodiode array detection and then confirmed by LC–ESI-MS. The quantification of components was performed using an internal standard (luteolin). This method may serve as a valuable tool for the quality evaluation of St. John’s Wort dietary supplement products.
food analysis, flavonoids, St. John’s Wort, Hypericum peforatum, naphthodianthrones, phloroglucinols
NCBI PubMed ID: 10949475Publication DOI: 10.1016/s0021-9673(00)00555-0Journal NLM ID: 9318488Publisher: Amsterdam; New York: Elsevier
Correspondence: Ang CYW
Institutions: US Food and Drug Administration, National Center for Toxicological Research, Division of Chemistry, Jefferson, USA
Methods: HPLC
- Article ID: 12487
Min BS, Nakamura N, Miyashiro H, Kim Y-H, Hattori M "Inhibition of human immunodeficiency virus type 1 reverse transcriptase and ribonuclease H activities by constituents of Juglans mandshurica" -
Chemical and Pharmaceutical Bulletin 48(2) (2000) 194-200
From the stem-bark of Juglans mandshurica, two new naphthalenyl glucopyranosides, 1, 4, 8-trihydroxy-nahthalene 1-O-[α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside] (1) and 1, 4, 8-trihydroxynaphthalene 1-O-β-D[6'-O-(3", 5"-dihydroxy-4"-methoxybenzoyl)]glucopyranoside (4), and two new α-tetralonyl glucopyranosides, 4α, 5, 8-trihydroxy-α-tetralone 5-O-β-D-[6'-O-(3", 5"-dihydroxy-4"-methoxybenzoyl)glucopyranoside (7) and 4α, 5, 8-trihydroxy-α-tetralone 5-O-β-D-[6'-O-(3", 4", 5"-trihydroxybenzoyl)glucopyranoside (8), were isolated together with three known naphthalenyl glucopyranosides (2, 3 and 5), one α-tetralonyl glucopyranoside (6), four flavonoids (9-12), and two gaalloyl glucopyranosides (13, 14).Amongst the isolated compounds, 1, 2, 6-trigalloylglucopyranose (13) and 1, 2, 3, 6-tertagalloylglucopyranose (14) exhibited the most potent inhibition of reverse transcriptase (RT) activity with IC50 values of 0.067 and 0.040 μM, respectively, while the latter compound also inhibited ribonuclease H (RNase H) activity with an IC50 of 39 μM, comparable in potency to illimaquinone used as a positive contorl. 1, 4, 8-Trihydroxy-naphthalene 1-O-β-D-glucopyranoside (2), 1, 4, 8-trihydroxynaphthalene 1-O-β-D-[6'-O-(4"-hydroxy-3", 5"-dimethoxybenzoyl)]glu-copyranoside (3) and 8 showed moderate inhibition against both enyzme activities, and inhibitory potency of 2 against RNase H activity (IC50=156 μM) was slightly greater than that against the RT activity (IC50=290 μM).The inhibitory potencies of 4α, 5, 8-trihydroxy-α-tetralone 5-O-β-D-[6'-O-4"-hydroxy-3", 5"-dimethoxybenzoyl)] glucopyranoside (6), 7 and 8 against RT activity increased accompanied by an increase in the number of free hydroxyls on the galloyl residues, as represented by the IC50 values of >500, 330 and 5.8 μM, respectively.
reverse transcriptase, Juglans mandshurica, human immunodeficienc virus, naphthalenyl glucopyranoside, ribonuclease H, α-tetralonyl glucopyranoside
NCBI PubMed ID: 10705503Publication DOI: 10.1248/cpb.48.194Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: College of Pharmacy, Chungnam National University, Taejeon, South Korea, Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, Toyama, Japan
Methods: biological assays
- Article ID: 12501
Morand C, Manach C, Crespy V, Rémésy C "Respective bioavailability of quercetin aglycone and its glycosides in a rat model" -
BioFactors 12(1-4) (2000) 169-174
A large number of flavonoids, mostly O-glycosides, are found in foods of plant origin. The bound sugar moiety is known to influence their bioavailability. We examined here the effect of the nature of the sugar on the absorption of the glycosides. Four groups of rats (n=6) received a meal containing 20 mg of quercetin equivalents supplied as aglycone, quercetin 3-glucoside, quercetin 3-rhamnoside or rutin. Plasma were hydrolysed by a βglucuronidase/sulfatase and analyzed by HPLC coupled to UV detection at 370 nm. Four hours after the beginning of the meal, the quercetin metabolites present in plasma were identical in all groups but their total concentrations were quite different. With pure quercetin the circulating levels were 11.7± 1.8 μM, but this level was three fold higher when quercetin was supplied as quercetin 3-glucoside (33.2± 3.5 μM). By contrast, the plasma concentrations of quercetin metabolites was quite low with the rutin meal (about 3 μM) and undetectable after the quercetin 3-rhamnoside meal. These data suggest that the 3-O-glucosylation improves the absorption of quercetin in the small intestine, whereas the binding of a rhamnose or of a glucose-rhamnose moiety to the aglycone markedly depressed its absorption. Additionnal experiments have shown that the higher plasma levels measured after the meal containing quercetin 3-glucoside compared to quercetin were maintained throughout a 24 hour period following the meal. In conclusion, the nature of the glycosylation markedly influences the efficiency of quercetin absorption in rats. Quercetin 3-glucose can be absorbed in the small intestine and is better absorbed than quercetin itself. By contrast, glycosides containing a rhamnose moiety could not be absorbed in the small intestine.
quercetin, quercetin glycosides, intestinal absorption, plasma metabolites
NCBI PubMed ID: 11216481Publication DOI: 10.1002/biof.5520120127Journal NLM ID: 8807441Publisher: Oxford; Washington, DC: IRL Press, International Union of Biochemistry
Correspondence: cmorand@clermont.inra.fr
Institutions: Unité des Maladies Métaboliques et des Micronutriments, INRA Theix, Ceyrat, France
Methods: biological assays, HPLC
- Article ID: 12552
Nyiredy S "Solid-liquid extraction strategy on the basis of solvent characterization" -
Chromatographia 51 (2000) ID S288-S296
Different solvents used for extraction are characterized on the basis of the Snyder theory. The individual solvent strength (si) and selectivity values (sv) of the solvents are used to formulate an extraction strategy by use of selected solvents, in a manner similar to that used for the computer-aided HPLC and TLC “PRISMA” mobile phase optimization procedures. After a pre-assay using the nine proposed solvents, twelve measurements are necessary to obtain the global optimum. The new method allows successful solid-liquid extraction of compounds from biological matrices such as medicinal and aromatic plants. Data obtained from furocoumarin isomers and flavonoid glycosides extracted from different medicinal and aromatic plants are used to demonstrate the validity of the method. The structures and properties of the compounds to be extracted do not have to be known for the procedure to be used.
solid-liquid extraction, extraction strategy, solvent characterization, "PRISMA" system, phytopharmaceuticals
Publication DOI: 10.1007/BF02492820Journal NLM ID: 0316520Publisher: Friedr. Vieweg Und Sohn Verlags Gmbh
Institutions: Research Institute for Medicinal Plants, Budakalász, Hungary
Methods: TLC, HPLC, extraction
- Article ID: 12559
Okada Y, Miyauchi N, Suzuki K, Kobayashi T, Tsutsui C, Mayuzumi K, Nishibe S, Okuyama T "Search for naturally occurring substances to prevent the complications of diabetes. II. Inhibitory effect of coumarin and flavonoid derivatives on bovine lens aldose reductase and rabbit platelet aggregation" -
Chemical and Pharmaceutical Bulletin 43(8) (1995) 1385-1387
An EtOAc extract of Artemisiae Capillari Spica inhibited both bovine lens aldose reductase (bovine-LAR) and rabbit platelet aggregation. Two simple coumarins, scoparone (1) and scopoletin (2), and three flavonoids, capillarisin (21), cirsimaritin (22) and rhamnocitrin (23), were isolated from this extract. Scoparone (1) and scopoletin (2) exhibit a potent inhibitory effect on rabbit platelet aggregation induced by four types of agent, ADP, PAF, sodium arachidonate and/or collagen. Capillarisin (21) exhibits a potent inhibitory effect on bovine-LAR. In addition, thirteen simple coumarins, five coumarin glycosides and two flavonoids were tested for their inhibitory effect against bovine-LAR and rabbit platelet aggregation.
flavonoid, diabetic complication, platelet aggregation, coumarin, Artemisiae Capillari Spica, bovine lens aldose reductase
NCBI PubMed ID: 7553983Publication DOI: 10.1248/cpb.43.1385Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Department of Pharmacognosy and Phytochemistry, Meiji College of Pharmacy Research Laboratories of Biological Science, Kodama Limited Department of Pharmacognosy, Faculty of Pharmaceutical Sciences, Health Science University of Hokkaido
Methods: inhibition studies, biological assays, extraction
- Article ID: 12578
Palomino O, Gómez-Serranillos MP, Slowing K, Carretero E, Villar A "Study of polyphenols in grape berries by reversed-phase high-performance liquid chromatography" -
Journal of Chromatography A 870(1-2) (2000) 449-451
Several polyphenols have been tested in grape berries from Spain. The flavonoid content is important because of the pharmacological properties of these compounds, whereas resveratrol has been proved to be an antifungal, antiinflammatory and an anticarcinogenic compound. A reversed-phase HPLC method has been developed and applied to determine resveratrol, quercetine, quercitrine and rutine content in several grape berries samples in a single analysis. Covering the grapes with a preservative paper yields a healthier product, but one which has a lower polyphenol content than unprotected grapes.
fruits; food analysis; polyphenols; flavonoids
NCBI PubMed ID: 10722101Publication DOI: 10.1016/s0021-9673(99)01225-xJournal NLM ID: 9318488Publisher: Amsterdam; New York: Elsevier
Correspondence: Gómez-Serranillos MP
Institutions: Department of Pharmacology, Faculty of Pharmacy, Universidad Complutense de Madrid, Madrid, Spain
Methods: extraction, RP-HPLC
- Article ID: 12579
Panizzi L, Catalano S, Miarelli C, Cioni PL, Campeol E "In vitro antimicrobial activity of extracts and isolated constituents of Geum rivale" -
Phytotherapy Research 14(7) (2000) 561-563
The antimicrobial activity of extracts of Geum rivale (Rosaceae) and that of some isolated constituents, on bacteria and fungi, was evaluated. The activity was concentrated in the triterpenes fraction and, for gram+ and gram- bacteria, also in the flavonoids fraction.
Geum rivale; Rosaceae; triterpenes; flavonoids; tannins; antimicrobial activity
NCBI PubMed ID: 11054853Publication DOI: 10.1002/1099-1573(200011)14:7<561::aid-ptr651>3.0.co;2-hJournal NLM ID: 8904486Publisher: Chichester: Wiley
Institutions: Dipartimento di Bioorganica e Biofarmacia, Università di Pisa, Pisa, Italy, Sezione di Biotossicologia, Dipartimento di Prevenzione A.U.S.L., Livorno, Italy
Methods: biological assays
- Article ID: 12642
Salatino A, Salatino MLF, Giannasi DE "Flavonoids and the taxonomy of Cercis" -
Biochemical Systematics and Ecology 28(6) (2000) 545-550
Flavonoids of 11 samples of Cercis, comprising seven species, were isolated and identified. Only 3-O-monoglycosides of kaempferol, quercetin and myricetin were obtained. Bauhinia (the largest genus in tribe Cercideae) is akin to Cercis because flavones are rarely found in the former. On the other hand, species of Bauhinia often present glycosides of isorhamnetin and a wider diversity of glycosides, and only rarely present myricetin. The frequent occurrence of this flavonol and the simpler flavonoid profile of Cercis may reflect a greater antiquity of Cercis as compared with Bauhinia. With the exception of C. canadensis var. mexicana, Cercis taxa from xerophytic habitats did not yield kaempferol glycosides in detectable amounts, as opposed to taxa from mesophytic habitats. The results obtained are consistent with proposals of merging C. reniformis into synonymy of C. occidentalis, as well as the recognition of two North American species, C. canadensis and C. occidentalis, and the recognition of the Asian C. gigantea.
Cercis; Cercideae; flavonoids; myricetin; chemotaxonomy
NCBI PubMed ID: 10793254Publication DOI: 10.1016/s0305-1978(99)00093-9Journal NLM ID: 0430442Publisher: Pergamon Press
Correspondence: Salatino A
Institutions: Department of Botany, University of Georgia, Athens, USA, Institute of Biosciences, University of São Paulo, São Paulo, Brazil
Methods: paper chromatography, extraction, CC, evaporation
- Article ID: 12711
Souleman AMA, El-Moussalamy AMD "Chemical investigation of the constitutive phenolics of Rosa arabica; the structure of a new dimeric phenolic glycoside" -
Natural Product Sciences 6(2) (2000) 82-85
The aqueous ethanolic whole plant extract of Rosa arabica was found to contain the new natural dimeric phenolic compound, ellagic acid 3,3'-dimethyl ether 4−O−α−rhamnopyranoside, 9, along with ten known phenolic metabolites (1-8, 10 and 11). Structures of all compounds (1-11) were established by routine methods of analysis and confirmed by FAB-MS, 1H and 13C NMR spectral analysis.
NMR, FAB-MS, rosaceae, Rosa arabica, dimeric phenolic glycoside, ellagic acid 3, 3'-dimethyl ether 4−O−α−rhamnopyranoside
Journal NLM ID: 9714997WWW link: http://kpubs.org/article/articleMain.kpubs?articleANo=E1HSBY_2000_v6n2_82Publisher: Seoul, Korea: Korean Society of Pharmacognosy
Institutions: National Research Centre, Cairo, Egypt, Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt
Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, enzymatic hydrolysis, acid hydrolysis, HPLC, UV, extraction, optical rotation measurement, melting point determination, HR-FAB-MS
- Article ID: 12721
Strick R, Strissel PL, Borgers S, Smith SL, Rowley JD "Dietary bioflavonoids induce cleavage in the MLL gene and may contribute to infant leukemia" -
Proceedings of the National Academy of Sciences of the USA 97(9) (2000) 4790-4795
Chromosomal translocations involving the MLL gene occur in about 80% of infant leukemia. In the search for possible agents inducing infant leukemia, we identified bioflavonoids, natural substances in food as well as in dietary supplements, that cause site-specific DNA cleavage in the MLL breakpoint cluster region (BCR) in vivo. The MLL BCR DNA cleavage was shown in primary progenitor hematopoietic cells from healthy newborns and adults as well as in cell lines; it colocalized with the MLL BCR cleavage site induced by chemotherapeutic agents, such as etoposide (VP16) and doxorubicin (Dox). Both in vivo and additional in vitro experiments demonstrated topoisomerase II (topo II) as the target of bioflavonoids similar to VP16 and Dox. Based on 20 bioflavonoids tested, we identified a common structure essential for topo II-induced DNA cleavage. Reversibility experiments demonstrated a religation of the bioflavonoid as well as the VP16-induced MLL cleavage site. Our observations support a two-stage model of cellular processing of topo II inhibitors: The first and reversible stage of topo II-induced DNA cleavage results in DNA repair, but also rarely in chromosome translocations; whereas the second, nonreversible stage leads to cell death because of an accumulation of DNA damage. These results suggest that maternal ingestion of bioflavonoids may induce MLL breaks and potentially translocations in utero leading to infant and early childhood leukemia.
doxorubicin, acute myelogenous leukemia, acute lymphoblastic leukemia, etoposide, topoisomerase II
NCBI PubMed ID: 10758153Publication DOI: 10.1073/pnas.070061297Journal NLM ID: 7505876Publisher: National Academy of Sciences
Correspondence: Strick R
; Strissel PL
Institutions: University of Chicago, Department of Medicine, Section of Hematology/Oncology, Chicago, IL, USA
Methods: biological assays
- Article ID: 12739
Tahrouch S, Andary C, Rapior S, Mondolot L, Gargadennec A, Fruchier A "Polyphenol investigation of Argania spinosa (Sapotaceae) endemic tree from Morocco" -
Acta Botanica Gallica : Bulletin De La Société Botanique De France 147(3) (2000) 225-232
The leaves of Argania spinosa from Morocco were investigated for flavonoids and condensed tannins. Four flavonol glycosides were identified by 1H NMR as myricitrin, quercitrin, hyperoside and myricetin 3-O-galactoside. UV spectrophotometric and histochemical methods were carried out to quantify and locate flavonoids and condensed tannins from leaves, stems and thorns of A. spinosa. Both high content and cell localisation of total polyphenols could explain the Argan tree adaptation to aridity.
flavonol glycosides, Sapotaceae, condensed tannins, Argania spinosa, histochemistry
Publication DOI: 10.1080/12538078.2000.10515843Journal NLM ID: 100955707Publisher: La Société
Institutions: Laboratoire des Symbiotes Racinaires et de Biochimie Végétale, Département de Biologie, Faculté des Sciences, Université Ibnou Zohr, Agadir, Maroc, Laboratoire de Botanique, Phytochimie et Mycologie, UMI—CNRS (UPR 9056, CEFE), Faculté de Pharmacie, Université Montpellier I, Montpellier, France, Laboratoire de Chimie Organique, Ecole Nationale Supérieure de Chimie, Montpellier, France
Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, TLC, ESI-MS, HPLC, extraction, CC
- Article ID: 12753
Tekel'ová D, Repčák M, Zemková E, Tóth J "Quantitative changes of dianthrones, hyperforin and flavonoids content in the flower ontogenesis of Hypericum perforatum" -
Planta Medica 66(8) (2000) 778-780
Samples of Hyperici herba were obtained by harvesting Hypericum perforatum L. in different plant development stages. The relation of flower development phases in the drug's flower fraction was examined. The HPLC method was then employed for the analysis of the content of secondary metabolites in different flower ontogenesis phases. The content of dianthrones, derivatives of quercetin and hyperforin increased from the first bud phases (0.29 %, 0.80 %, and 2.47 %, respectively) to flowers just opened (1.04 %, 4.23 % and 6.60 %, respectively). The content of dianthrones and quercetin glycosides then decreased (in unripe fruits 0.11 % and 0.08 %, respectively), whereas the amounts of hyperforin increased to 8.07 % in fruits. The content of I3,II8-biapigenin increased from 0.21 % in small buds to 1.04 % in buds just before opening and has then decreased gradually to a value of 0.02 % in fruits. Rutin was not detected in the samples.
flavonoids, different parts of plant, Hypericum perforatum var. angustifolium, dianthrones, hyperforin
NCBI PubMed ID: 11199145Publication DOI: 10.1055/s-2000-9779Journal NLM ID: 0066751Publisher: George Thieme
Correspondence: tekelova@fpharm.uniba.sk
Institutions: Department of Pharmacognosy and Botany, Faculty of Pharmacy, Comenius University, Bratislava, Slovakia, Department of Experimental Botany and Genetics, Faculty of Natural Sciences, P.J. Šafárik University, Košice, Slovakia
- Article ID: 12881
Yu SJ, Abo-Elghar GE "Allelochemicals as inhibitors of glutathione S-transferases in the fall armyworm" -
Pesticide Biochemistry and Physiology 68(3) (2000) 173-183
Glutathione S-transferases (GSTs) isolated from larval midguts of the fall armyworm, Spodoptera frugiperda, were used to study their sensitivity to inhibition by 44 chemicals, most of which were plant allelochemi cals. Many flavonoids, other phenols, and α,β-unsaturated carbonyl compounds were potent inhibitors of the enzymes. For the flavonoids, apigenin was the best inhibitor among those studied, showing an I50 value of 0.82 μM. In general, flavonols exhibited higher inhibitory potencies than flavones; flavonoid glycosides were less inhibitory than their corresponding aglycones. In the case of phenols, tannic acid was the best inhibitor among those tested, showing an I50 value of 0.2 μM. The organotin compound chlorotriphenyltin was an potent as tannic acid in inhibiting the transferases. For the αβ-unsaturated carbonyl compounds, ethacrynic acid was the most potent inhibitor among those examined, showing an I50 value of 0.15 μM. However, the isothiocyanates were found to be marginal inhibitors of GSTs. GSTs isolated from larval fat bodies showed differential sensitivity to inhibition by some selected inhibitors compared with midgut GSTs. Kinetic studies of midgut GSTs revealed that ellagic acid exhibited a noncompetitive inhibition toward 1-chloro-2, 4-dinitrobenzene (CDNB) but a competitive inhibition toward glutathione (GSH). In contrast, inhibition by tannic acid and ethacrynic acid were noncompetitive toward both CDNB and GSH. Diethyl maleate did not affect GSH levels in midguts when larvae were topically treated with this compound for up to 24 h.
inhibition, flavonoids, glutathione S-transferase, Spodoptera frugiperda
Publication DOI: 10.1006/pest.2000.2514Journal NLM ID: 1301573Publisher: New York: Academic Press
Institutions: Department of Entomology and Nematology, University of Florida, Gainesville, USA
Methods: biological assays
- Article ID: 12885
Yuldashev MP, Batirov EK "A novel isoflavone glycoside from Caragana alaica" -
Russian Journal of Bioorganic Chemistry 26(11) (2000) 787-789
3-O-Rhamnopyranosylisorhamnetin, 3-O-glucopyranosylisorhamnetin, 7-O-galactopyranosylluteolin, quercitrin, isoquercitrin, wistin, and a novel isoflavonoid, 3′-hydroxy-6,4′-dimethoxy-7-O-β-D-glucopyranosylisoflavone, were isolated from the aerial parts of Caragana alaica. Of these, the previously described compounds were identified on the basis of their physicochemical and spectral characteristics, whereas the spectral analysis and conversion to a known compound, cladrastin, allowed the structural elucidation of the novel isoflavone glycoside.
Caragana alaica, 3′-hydroxy-6, 4′-dimethoxy-7-O-β-D-glucopyranosylisoflavone, 3-O-rhamnopyranosylisorhamnetin, 3-O-glucopyranosylisorhamnetin, 7-O-galactopyranosylluteolin
NCBI PubMed ID: 11696899Publication DOI: 10.1007/BF02759633Journal NLM ID: 9420101Publisher: Springer Science and Business Media
Institutions: Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Republic of Uzbekistan, Tashkent, Uzbekistan
Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, enzymatic hydrolysis, acid hydrolysis, HPLC, UV, extraction, optical rotation measurement, melting point determination, HR-FAB-MS
Expand this compound
Collapse this compound
3. Compound ID: 27630
|
b-D-1dGlcp-(1C-8)-Subst
Subst = daidzein = SMILES O=C1C(C2=CC={54}C(O)C=C2)=COC3=C1C=C{7}C(O)={8}C3 |
Show graphically |
Structure type: monomer
Trivial name: puerarin
Compound class: glycoside, C-glycoside, flavonoid glycoside
The structure is contained in the following publication(s):
- Article ID: 11088
Hirakura K, Morita M, Nakajima K, Sugama K, Takagi K, Niitsu K, Ikeya Y, Maruno M, Okada M "Phenolic glucosides from the root of Pueraria lobata" -
Phytochemistry 46(5) (1997) 921-928
Six phenolic glucosides were isolated from the methanolic extract of the root of Pueraria lobata. Three of them were new compounds and their structures were proved to be kuzubutenolide A, 3'-hydroxy-4'-O-β-D-glucosylpuerarin and 3'-methoxydaidzin.
root, Leguminosae, Pueraria lobata, isolfavone, butenolide, 6”-O-malonyldaidzin, kuzubutenolide A, 3’-hydroxy-4’-O-b-D-glucosylpuerarin, 3’-methoxydaidzin
Publication DOI: 10.1016/S0031-9422(97)00371-3Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Central Research Laboratories, Tsumura & Co., 3586 Yoshiwara, Ami-machi, Inashiki-gun, Ibaraki, 300-l I, Japan
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, IR, FAB-MS, X-ray, TLC, enzymatic hydrolysis, acid hydrolysis, GLC, methanolysis, HPLC
- Article ID: 12005
Ashida H, Fukuda I, Yamashita T, Kanazawa K "Flavones and flavonols at dietary levels inhibit a transformation of aryl hydrocarbon receptor induced by dioxin" -
FEBS Letters 476(3) (2000) 213-217
Dioxins invade the body mainly through the diet, and produce toxicity through the transformation of aryl hydrocarbon receptor (AhR). An inhibitor of the transformation should therefore protect against the toxicity and ideally be part of the diet. We examined flavonoids ubiquitously expressed in plant foods as one of the best candidates, and found that the subclasses flavones and flavonols suppressed antagonistically the transformation of AhR induced by 1 nM of 2,3,7,8-tetrachlorodibenzo-p-dioxin, without exhibiting agonistic effects that transform AhR. The antagonistic IC(50) values ranged from 0.14 to 10 μM, close to the physiological levels in human.
flavonoid, cancer prevention, dioxin antagonist, aryl hydrocarbon receptor, transformation inhibitor, dietary phytochemical
NCBI PubMed ID: 10913616Publication DOI: 10.1016/s0014-5793(00)01730-0Journal NLM ID: 0155157Publisher: Elsevier
Correspondence: Kanazawa K
Institutions: Laboratory of Food and Nutritional Chemistry, Faculty of Agriculture, Kobe University, Kobe, Japan
Methods: DNA techniques, biological assays, radiolabeling, centrifugation, autoradiography
- Article ID: 12072
Cheng G, Bai Y, Zhao Y, Tao J, Liu Y, Tu G, Ma L, Liao N, Xu X "Flavonoids from Ziziphus jujuba Mill var. spinosa" -
Tetrahedron 56(45) (2000) 8915-8920
Eight flavonoid compounds were isolated from the seeds of Ziziphus jujuba Mill var. Spinosa. On the basis of chemical and spectral analyses their structures were elucidated as swertish (1), puerarin (2), 6‴-feruloylspinosin (3), apigenin-6-C-β-D-glucopyranoside (4), spinosin (5), 6‴-feruloylisospinosin (6), isospinosin (7), and isovitexin-2″-O-β-D-glucopyranoside (8). Flavonoids 6 and 7 are novel compounds. Rotamers exist for compounds 1, 3 and 5, which are reported for the first time. Compounds 2, 4 and 8 were isolated from this plant for the first time. Spinosin and swertish possess significant sedative activity.
flavonoid, Ziziphus jujuba Mill var. spinosa, flavone-C-glycoside, conformers, spinosin, 6'''-feruloylisospinosin, isospinosin, sedative activity
Publication DOI: 10.1016/S0040-4020(00)00842-5Journal NLM ID: 2984170RPublisher: Pergamon Press
Correspondence: Zhao Y
Institutions: College of Chemistry and Molecular Engineering, Peking University, Beijing, China, Beijing Institute of Microchemistry, Beijing, China, Division of Natural Medicinal Chemistry, Beijing Medical University, Beijing, China
Methods: 13C NMR, 1H NMR, TLC, acid hydrolysis, HPLC, UV, extraction, CC, melting point determination, HR-FAB-MS, MALDI-TOF/MS
- Article ID: 12225
He X-G "On-line identification of phytochemical constituents in botanical extracts by combined high-performance liquid chromatographic–diode array detection–mass spectrometric techniques" -
Journal of Chromatography A 880(1-2) (2000) 203-232
It is necessary to determine all of the phytochemical constituents of botanical extracts in order to ensure the reliability and repeatability of pharmacological and clinical research, to understand their bioactivities and possible side effects of active compounds and to enhance product quality control. HPLC chromatographic fingerprints can be applied for this kind of documentation. Combined HPLC-diode array detection-MS techniques can provide on-line UV and MS information for each peak in a chromatogram. In most cases, direct identification of the peaks is possible, based on comparison with published data or with standard compounds. This review will primarily focus on electrospray and thermospray ionization MS and their applications for the qualitative analyses of phenolic compounds, saponins, alkaloids and other classes of natural products in botanical extracts. Twenty-one of the most commonly used herbal examples, their phytochemical analyses and characteristics of their mass spectra are described.
alkaloids, saponins, plant materials, flavonoids, phenolic compounds, reviews
NCBI PubMed ID: 10890521Publication DOI: 10.1016/s0021-9673(00)00059-5Journal NLM ID: 9318488Publisher: Amsterdam; New York: Elsevier
Institutions: Research Laboratory of Natural Products Chemistry, A. M. Todd Botanicals, Eugene, USA
Expand this compound
Collapse this compound
4. Compound ID: 27754
|
a-D-GlcpA4Ac-(1-2)-+
|
-4)-b-D-Xylp2Ac3Ac-(1-4)-b-D-Xylp3Ac-(1-4)-b-D-Xylp3Ac-(1-4)-b-D-Xylp-(1-4)-b-D-Xylp2Ac-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: xylan
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_140630,IEDB_167188,IEDB_174332
The structure is contained in the following publication(s):
- Article ID: 11117
Puls, J "Chemistry and biochemistry of hemicelluloses: Relationship between hemicellulose structure and enzymes required for hydrolysis" -
Macromolecular Symposia 120 (1997) 183-196
The lignified plant cell wall is a composite material in which cellulose, hemicelluloses and lignin are in tight association. Xylans constitute the predominant hemicellulose of hardwoods and straw, wherease galactomannans represent the largest hemicellulose fraction in softwoods. Naturally occuring hemicelluloses, commercially available hemicelluloses and xylans and mannans from technical processes have distinct differences with respect to degree of polymerization and extent of branching. In principle, naturally occuring hemicelluloses carry more side chains compared to those which have been extracted with alkali or under pressure and heat. The presence or absence of substituents is also reflected by the enzymes required for complete hydrolysis. The action of the depolymerizing xylanases and mannanases may be partly dependent on debranching enzymes. Special empasis is therefore given on the substrate requirements of the so-called accessory enzymes (i.e. α-glucuronidase, α-arabinosidase, α-galactosidase, acetyl-and phenolic acid esterase) as well as on synergy effects with the depolymerizing enzymes.
Publication DOI: 10.1002/masy.19971200119Journal NLM ID: 9888296Publisher: Basel; Oxford, CT: Hüthig & Wepf
Institutions: Federal Research Centre of Forestry and Forest Products, Institute of Wood Chemistry, D-21031 Hamburg
Expand this compound
Collapse this compound
5. Compound ID: 27755
|
-4)-b-D-Manp-(1-4)-b-D-Glcp-(1-4)-b-D-Manp-(1-4)-b-D-Manp-(1-4)-b-D-Glcp-(1-4)-b-D-Manp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: glucomannan
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_137485,IEDB_142488,IEDB_144983,IEDB_146664,IEDB_152206,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_72
The structure is contained in the following publication(s):
- Article ID: 11117
Puls, J "Chemistry and biochemistry of hemicelluloses: Relationship between hemicellulose structure and enzymes required for hydrolysis" -
Macromolecular Symposia 120 (1997) 183-196
The lignified plant cell wall is a composite material in which cellulose, hemicelluloses and lignin are in tight association. Xylans constitute the predominant hemicellulose of hardwoods and straw, wherease galactomannans represent the largest hemicellulose fraction in softwoods. Naturally occuring hemicelluloses, commercially available hemicelluloses and xylans and mannans from technical processes have distinct differences with respect to degree of polymerization and extent of branching. In principle, naturally occuring hemicelluloses carry more side chains compared to those which have been extracted with alkali or under pressure and heat. The presence or absence of substituents is also reflected by the enzymes required for complete hydrolysis. The action of the depolymerizing xylanases and mannanases may be partly dependent on debranching enzymes. Special empasis is therefore given on the substrate requirements of the so-called accessory enzymes (i.e. α-glucuronidase, α-arabinosidase, α-galactosidase, acetyl-and phenolic acid esterase) as well as on synergy effects with the depolymerizing enzymes.
Publication DOI: 10.1002/masy.19971200119Journal NLM ID: 9888296Publisher: Basel; Oxford, CT: Hüthig & Wepf
Institutions: Federal Research Centre of Forestry and Forest Products, Institute of Wood Chemistry, D-21031 Hamburg
Expand this compound
Collapse this compound
6. Compound ID: 27756
|
a-D-GlcpA4Ac-(1-2)-+
|
a-L-Araf-(1-3)-+ | Fer-(9-5)-a-L-Araf-(1-3)-+
| | |
-4)-b-D-Xylp-(1-4)-b-D-Xylp-(1-4)-b-D-Xylp-(1-4)-b-D-Xylp3Ac-(1-4)-b-D-Xylp-(1-
Fer = ferulic acid |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: arabinoxylan
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_136907,IEDB_140630,IEDB_150942,IEDB_167188,IEDB_174332
The structure is contained in the following publication(s):
- Article ID: 11117
Puls, J "Chemistry and biochemistry of hemicelluloses: Relationship between hemicellulose structure and enzymes required for hydrolysis" -
Macromolecular Symposia 120 (1997) 183-196
The lignified plant cell wall is a composite material in which cellulose, hemicelluloses and lignin are in tight association. Xylans constitute the predominant hemicellulose of hardwoods and straw, wherease galactomannans represent the largest hemicellulose fraction in softwoods. Naturally occuring hemicelluloses, commercially available hemicelluloses and xylans and mannans from technical processes have distinct differences with respect to degree of polymerization and extent of branching. In principle, naturally occuring hemicelluloses carry more side chains compared to those which have been extracted with alkali or under pressure and heat. The presence or absence of substituents is also reflected by the enzymes required for complete hydrolysis. The action of the depolymerizing xylanases and mannanases may be partly dependent on debranching enzymes. Special empasis is therefore given on the substrate requirements of the so-called accessory enzymes (i.e. α-glucuronidase, α-arabinosidase, α-galactosidase, acetyl-and phenolic acid esterase) as well as on synergy effects with the depolymerizing enzymes.
Publication DOI: 10.1002/masy.19971200119Journal NLM ID: 9888296Publisher: Basel; Oxford, CT: Hüthig & Wepf
Institutions: Federal Research Centre of Forestry and Forest Products, Institute of Wood Chemistry, D-21031 Hamburg
Expand this compound
Collapse this compound
7. Compound ID: 27757
|
a-D-GlcpA4Ac-(1-2)-+ a-L-Araf-(1-3)-+
| |
-4)-b-D-Xylp-(1-4)-b-D-Xylp-(1-4)-b-D-Xylp-(1-4)-b-D-Xylp-(1-4)-b-D-Xylp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: arabino-4-O-methylglucuronoxylan
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_136907,IEDB_140630,IEDB_167188,IEDB_174332
The structure is contained in the following publication(s):
- Article ID: 11117
Puls, J "Chemistry and biochemistry of hemicelluloses: Relationship between hemicellulose structure and enzymes required for hydrolysis" -
Macromolecular Symposia 120 (1997) 183-196
The lignified plant cell wall is a composite material in which cellulose, hemicelluloses and lignin are in tight association. Xylans constitute the predominant hemicellulose of hardwoods and straw, wherease galactomannans represent the largest hemicellulose fraction in softwoods. Naturally occuring hemicelluloses, commercially available hemicelluloses and xylans and mannans from technical processes have distinct differences with respect to degree of polymerization and extent of branching. In principle, naturally occuring hemicelluloses carry more side chains compared to those which have been extracted with alkali or under pressure and heat. The presence or absence of substituents is also reflected by the enzymes required for complete hydrolysis. The action of the depolymerizing xylanases and mannanases may be partly dependent on debranching enzymes. Special empasis is therefore given on the substrate requirements of the so-called accessory enzymes (i.e. α-glucuronidase, α-arabinosidase, α-galactosidase, acetyl-and phenolic acid esterase) as well as on synergy effects with the depolymerizing enzymes.
Publication DOI: 10.1002/masy.19971200119Journal NLM ID: 9888296Publisher: Basel; Oxford, CT: Hüthig & Wepf
Institutions: Federal Research Centre of Forestry and Forest Products, Institute of Wood Chemistry, D-21031 Hamburg
Expand this compound
Collapse this compound
8. Compound ID: 27758
|
a-D-Galp-(1-6)-+
|
-4)-b-D-Manp3Ac-(1-4)-b-D-Manp-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp3Ac-(1-4)-b-D-Manp3Ac-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: acetylgalactoglucucomannan
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_137485,IEDB_140116,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 11117
Puls, J "Chemistry and biochemistry of hemicelluloses: Relationship between hemicellulose structure and enzymes required for hydrolysis" -
Macromolecular Symposia 120 (1997) 183-196
The lignified plant cell wall is a composite material in which cellulose, hemicelluloses and lignin are in tight association. Xylans constitute the predominant hemicellulose of hardwoods and straw, wherease galactomannans represent the largest hemicellulose fraction in softwoods. Naturally occuring hemicelluloses, commercially available hemicelluloses and xylans and mannans from technical processes have distinct differences with respect to degree of polymerization and extent of branching. In principle, naturally occuring hemicelluloses carry more side chains compared to those which have been extracted with alkali or under pressure and heat. The presence or absence of substituents is also reflected by the enzymes required for complete hydrolysis. The action of the depolymerizing xylanases and mannanases may be partly dependent on debranching enzymes. Special empasis is therefore given on the substrate requirements of the so-called accessory enzymes (i.e. α-glucuronidase, α-arabinosidase, α-galactosidase, acetyl-and phenolic acid esterase) as well as on synergy effects with the depolymerizing enzymes.
Publication DOI: 10.1002/masy.19971200119Journal NLM ID: 9888296Publisher: Basel; Oxford, CT: Hüthig & Wepf
Institutions: Federal Research Centre of Forestry and Forest Products, Institute of Wood Chemistry, D-21031 Hamburg
Expand this compound
Collapse this compound
9. Compound ID: 31207
|
a-L-Rhap-(1-6)-b-D-Glcp-(1-7)-Subst
Subst = naringenin = SMILES O=C1CC(C2=CC={54}C(O)C=C2)OC3=C{7}C(O)={6}C{5}C(O)=C13 |
Show graphically |
Structure type: oligomer
Trivial name: naringin, narirutin, narurutin
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144144,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 11991
Aikawa J, Ishii T, Kuramoto M, Kadoya K "Growth stimulants for vesicular-arbuscular mycorrhizal fungi in satsuma mandarin pomace" -
Engei Gakkai Zasshi = Journal of the Japanese Society for Horticultural Science 69(4) (2000) 385-389
The isolation and identification of growth stimulants for vesicular-arbuscular mycorrhizal (VAM) fungi in the 25% methanol (MeOH) extracts of satsuma mandarin (Citrus unshiu Marc.) pomace extracts were carried out. Three compounds were isolated from the eluates by using a high pressure liquid chromatography (HPLC). When the effect of the three compounds was tested on the in vitro hyphal growth of a VAM fungus, Gigaspora margarita, two compounds had a stimulatory effect. The two stimulants were identified as hesperidin (hesperetin-7-β-rutinoside) and narirutin (naringenin-7-β-rutinoside). Narirutin at 1 to 30 ppm and hesperidin at 1 to 10 ppm significantly stimulated the hyphal growth of G. margarita.
flavonoids, hesperidin, narirutin, satsuma mandarin pomace, vesicular-arbuscular mycorrhizal stimulants
Publication DOI: 10.2503/JJSHS.69.385Journal NLM ID: 100955355Publisher: Tokyo
Institutions: Faculty of Agriculture, Ehime University, Matsuyama, Japan, Faculty of Agriculture, Kyoto Prefectural University, Kyoto, Japan, Advanced Instrumentation Center for Chemical Analysis, Ehime University, Matsuyama, Japan
Methods: 1H NMR, EI-MS, biological assays, HPLC, extraction, evaporation, flash chromatography, light microscopy
- Article ID: 12005
Ashida H, Fukuda I, Yamashita T, Kanazawa K "Flavones and flavonols at dietary levels inhibit a transformation of aryl hydrocarbon receptor induced by dioxin" -
FEBS Letters 476(3) (2000) 213-217
Dioxins invade the body mainly through the diet, and produce toxicity through the transformation of aryl hydrocarbon receptor (AhR). An inhibitor of the transformation should therefore protect against the toxicity and ideally be part of the diet. We examined flavonoids ubiquitously expressed in plant foods as one of the best candidates, and found that the subclasses flavones and flavonols suppressed antagonistically the transformation of AhR induced by 1 nM of 2,3,7,8-tetrachlorodibenzo-p-dioxin, without exhibiting agonistic effects that transform AhR. The antagonistic IC(50) values ranged from 0.14 to 10 μM, close to the physiological levels in human.
flavonoid, cancer prevention, dioxin antagonist, aryl hydrocarbon receptor, transformation inhibitor, dietary phytochemical
NCBI PubMed ID: 10913616Publication DOI: 10.1016/s0014-5793(00)01730-0Journal NLM ID: 0155157Publisher: Elsevier
Correspondence: Kanazawa K
Institutions: Laboratory of Food and Nutritional Chemistry, Faculty of Agriculture, Kobe University, Kobe, Japan
Methods: DNA techniques, biological assays, radiolabeling, centrifugation, autoradiography
- Article ID: 12055
Careri M, Elviri L, Mangia A, Musci M "Spectrophotometric and coulometric detection in the high-performance liquid chromatography of flavonoids and optimization of sample treatment for the determination of quercetin in orange juice" -
Journal of Chromatography A 881(1-2) (2000) 449-460
The capabilities of spectrophotometric and electrochemical detection techniques were investigated for the high-performance liquid chromatographic determination of flavonoids. Liquid chromatographic analyses were performed on eleven compounds belonging to three different classes of flavonoids: flavanone glycosides, flavone and flavonol aglycones. Separation of all compounds examined was carried out under reversed-phase conditions on a C18 narrow-bore column for UV detection, whereas for electrochemical detection, a C18 standard-bore column was used. UV analyses were carried out at 280 nm for flavanones and at 265 nm for flavones and flavonols, whereas controlled-potential coulometric measurements were performed using a porous graphite electrode. Analytical performances of the methods were compared in terms of linearity, limits of detection (LODs) and precision. Linearity over two orders of magnitude and LODs at low-ppm levels (0.06-1 mg/l) were demonstrated for all techniques considered. Instrumental precision in terms of relative standard deviation was found to be between 0 and 5% for the liquid chromatography (LC)-UV system and between 0.6 and 10% for the LC-electrochemical detection (ED) system. The methods developed were applied to the analysis of flavanones and flavonols in a real sample, such as an extract of orange juice. Even though quercetin glycoside is mostly present in orange juice as rutin, other different glycosides of this flavonol could be present; on this basis, the hydrolysis of all glycosides to aglycone allows one to obtain more accurate data on the flavonol concentration in orange juice. To avoid sample degradation and to increase extraction efficiency, quercetin hydrolysis was optimized using a central composite design to investigate the effects of acid concentration and hydrolysis time on extraction recovery.
experimental design, quercetin, food analysis, flavonoids, fruit juices, statistical analysis
NCBI PubMed ID: 10905727Publication DOI: 10.1016/s0021-9673(00)00256-9Journal NLM ID: 9318488Publisher: Amsterdam; New York: Elsevier
Correspondence: careri@unipr.it
Institutions: Dipartimento di Chimica Generale ed Inorganica, Chimica Analitica, Chimica Fisica, Università degli Studi di Parma, Parma, Italy
Methods: acid hydrolysis, HPLC, extraction, centrifugation, voltammetry
- Article ID: 12357
Leuzzi U, Caristi C, Panzera V, Licandro G "Flavonoids in pigmented orange juice and second-pressure extracts" -
Journal of Agricultural and Food Chemistry 48(11) (2000) 5501-5506
Flavanone glycosides (FGs) and polymethoxylated flavones (PMFs) have been studied in pigmented orange (Citrus sinensis) juices and second-pressure extracts (SPEs) by high-performance liquid chromatography and diode array detector. Detection was performed simultaneously at two different wavelengths: 278 nm (for determination of FGs) and 325 nm (for determination of PMFs). Qualitative distribution patterns of FGs and PMFs in juices and SPEs were similar, although the quantitative results are quite different. An increased narirutin/hesperidin ratio after centrifugation and the presence of high amounts of PMFs in SPEs, which remain unchanged after centrifugation, were observed. Therefore, a simple and affordable procedure to distinguish an orange juice from SPEs was proposed.
HPLC, flavonoids, orange juice, flavanone glycosides, second-pressure extracts, polymethoxylated flavones
NCBI PubMed ID: 11087509Publication DOI: 10.1021/jf000538oJournal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: leuzzi@isengard.unime.it
Institutions: Dipartimento di Chimica Organica e Biologica, Università di Messina, Messina, Italy, Citrus Vita - Zona Industriale Regionale, Messina, Italy
- Article ID: 12430
Ma Y-L, Vedernikova I, Van den Heuvel H, Claeys M "Internal glucose residue loss in protonated O-diglycosyl flavonoids upon low-energy collision-induced dissociation" -
Journal of the American Society for Mass Spectrometry 11(2) (2000) 136-144
The low-energy collision-induced dissociation of protonated flavonoid O-diglycosides, i.e., flavonoid O-rutinosides and O-neohesperidosides, containing different aglycone types has been studied. The results indicate that the unusual [M+H-162]+ ion formed by internal glucose residue loss, which in a previous study was shown to be a rearrangement ion, is strongly dependent upon the aglycone type. For 7-O-diglycosides, the internal glucose loss is very pronounced for aglycones of the flavanone type, but is completely absent for aglycones of the flavone and flavonol types. Internal glucose residue loss was found to correspond to a minor fragmentation pathway for flavonol 3-O-diglycosides. A plausible mechanism is proposed based on proton mobilization from the aglycone to the disaccharidic part of the flavonoid O-diglycosides which is supported by theoretical calculations and model building.
NCBI PubMed ID: 10689666Publication DOI: 10.1016/S1044-0305(99)00133-6Journal NLM ID: 9010412Publisher: Elsevier
Correspondence: claeys@uia.ua.ac.be
Institutions: Department of Pharmaceutical Sciences, University of Antwerp (UIA), Antwerp, Belgium
Methods: MS
- Article ID: 12476
Merken HM, Beecher GR "Measurement of food flavonoids by high-performance liquid chromatography: a review" -
Journal of Agricultural and Food Chemistry 48(3) (2000) 577-599
The flavonoids are plant polyphenols found frequently in fruits, vegetables, and grains. Divided into several subclasses, they include the anthocyanidins, pigments chiefly responsible for the red and blue colors in fruits, fruit juices, wines, and flowers; the catechins, concentrated in tea; the flavanones and flavanone glycosides, found in citrus and honey; and the flavones, flavonols, and flavonol glycosides, found in tea, fruits, vegetables, and honey. Known for their hydrogen-donating antioxidant activity as well as their ability to complex divalent transition metal cations, flavonoids are propitious to human health. Computer-controlled high-performance liquid chromatography (HPLC) has become the analytical method of choice. Many systems have been developed for the detection and quantification of flavonoids across one, two, or three subclasses. A summary of the various HPLC and sample preparation methods that have been employed to quantify individual flavonoids within a subclass or across several subclasses are tabulated in this review.
antioxidant; flavonoids; HPLC; mass spectrometry; polyphenols
NCBI PubMed ID: 10725120Publication DOI: 10.1021/jf990872oJournal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: merken@bhnrc.usda.gov
Institutions: Food Composition Laboratory, Beltsville Human Nutrition Research Center Agricultural Research Service, U.S. Department of Agriculture, Beltsville, USA
- Article ID: 12522
Ng TB, Liu F, Wang ZT "Antioxidative activity of natural products from plants" -
Life Sciences 66(8) (2000) 709-723
A variety of flavonoids, lignans, an alkaloid, a bisbenzyl, coumarins and terpenes isolated from Chinese herbs was tested for antioxidant activity as reflected in the ability to inhibit lipid peroxidation in rat brain and kidney homogenates and rat erythrocyte hemolysis. The pro-oxidant activities of the aforementioned compounds were assessed by their effects on bleomycin-induced DNA damage. The flavonoids baicalin and luteolin-7-glucuronide-6'-methyl ester, the lignan 4'-demethyldeoxypodophyllotoxin, the alkaloid tetrahydropalmatine, the bisbenzyl erianin and the coumarin xanthotoxol exhibited potent antioxidative activity in both lipid peroxidation and hemolysis assays. The flavonoid rutin and the terpene tanshinone I manifested potent antioxidative activity in the lipid peroxidation assay but no inhibitory activity in the hemolysis assay. The lignan deoxypodophyllotoxin, the flavonoid naringin and the coumarins columbianetin, bergapten and angelicin slightly inhibited lipid peroxidation in brain and kidney homogenates. It is worth stressing that the compounds with antioxidant effects in this assay, with the exception of tetrahydropalmatin and tanshinone I, have at least one free aromatic hydroxyl group in structure. Obviously, the aromatic hydroxyl group is very important for antioxidative effects of the compounds. None of the compounds tested exerted an obvious pro-oxidant effect.
plant, Antioxidant, hemolysis, peroxidation
NCBI PubMed ID: 10680579Publication DOI: 10.1016/s0024-3205(99)00642-6Journal NLM ID: 0375521Publisher: Amsterdam: Elsevier
Correspondence: Ng TB
Institutions: Department of Pharmacognosy, China Pharmaceutical University, Nanjing, China, Department of Microbiology, Nankai University, Tianjin, China, Department of Biochemistry, Faculty of Medicine, The Chinese University of Hong Kong, Hong Kong, China
Methods: biological assays
- Article ID: 12624
Ross SA, Ziska DS, Zhao K, ElSohly MA "Variance of common flavonoids by brand of grapefruit juice" -
Fitoterapia 71(2) (2000) 154-161
Nine commercial brands of grapefruit juice were analyzed for their flavonoid content by HPLC to determine if significant brand-to-brand variance in grapefruit juice flavonoid content exists. Flavonoid glycosides narirutin, naringin, hesperidin, neohesperidin, didymin, and poncirin have been identified in all the grapefruit juices examined. The aglycone quercetin was detected in only two brands. All the juices were free from methoxylated flavonoid aglycones. There was a significant difference in the amounts of total flavonoids and individual flavonoids in the nine brands. The concentration of total flavonoids ranged between 19.44 and 84.28 mg/100 ml juice. Naringin was found to be the major flavonoid followed by narirutin and hesperidin. Their concentrations ranged from 14.56 to 63.8; 2.25 to 12.20; and 0.24 to 3.12 mg/100 ml juice, respectively.
grapefruit juice; flavonoids; HPLC
NCBI PubMed ID: 10727812Publication DOI: 10.1016/s0367-326x(99)00131-8Journal NLM ID: 16930290RPublisher: Elsevier
Correspondence: dziska@pharmacy.umsmed.edu
Institutions: The National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, Mississippi, USA, Department of Pharmacognosy, University of Mississippi, School of Pharmacy, Mississippi, USA, Department of Clinical Pharmacy Practice, University of Mississippi, School of Pharmacy, Mississippi, USA, Department of Pharmaceutics, University of Mississippi, School of Pharmacy, Mississippi, USA
- Article ID: 12742
Takei H, Yoshizaki F "Determination of flavanone glycosides in various peels of Citrus fruits, immature Citrus fruits and Chinese medicinal prescriptions containing these crude drugs by using capillary electrophoresis" -
Bunseki Kagaku 49(8) (2000) 639-643
The determination of flavanone glycosides in various peels of Citrus fruits, immature Citrus fruits and Chinese medicinal prescriptions containing these crude drugs was performed by using capillary electrophoresis. The analytical procedure employed in this experiment seemed to be useful for the evaluation and quality control of these two crude drugs, but was applicable for estimating flavanone glycosides in only a few Chinese medicinal prescriptions.
capillary electrophoresis; flavanone glycosides; peel of Citrus fruit; immature Citrus fruit; Chinese medicinal prescription
WWW link: https://cir.nii.ac.jp/crid/1390001204052128384Publisher: The Japan Society for Analytical Chemistry
Institutions: Tohoku Pharmaceutical University, Sendai, Japan
Methods: extraction, capillary electrophoresis (CE)
Expand this compound
Collapse this compound
10. Compound ID: 31250
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_613439,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 12005
Ashida H, Fukuda I, Yamashita T, Kanazawa K "Flavones and flavonols at dietary levels inhibit a transformation of aryl hydrocarbon receptor induced by dioxin" -
FEBS Letters 476(3) (2000) 213-217
Dioxins invade the body mainly through the diet, and produce toxicity through the transformation of aryl hydrocarbon receptor (AhR). An inhibitor of the transformation should therefore protect against the toxicity and ideally be part of the diet. We examined flavonoids ubiquitously expressed in plant foods as one of the best candidates, and found that the subclasses flavones and flavonols suppressed antagonistically the transformation of AhR induced by 1 nM of 2,3,7,8-tetrachlorodibenzo-p-dioxin, without exhibiting agonistic effects that transform AhR. The antagonistic IC(50) values ranged from 0.14 to 10 μM, close to the physiological levels in human.
flavonoid, cancer prevention, dioxin antagonist, aryl hydrocarbon receptor, transformation inhibitor, dietary phytochemical
NCBI PubMed ID: 10913616Publication DOI: 10.1016/s0014-5793(00)01730-0Journal NLM ID: 0155157Publisher: Elsevier
Correspondence: Kanazawa K
Institutions: Laboratory of Food and Nutritional Chemistry, Faculty of Agriculture, Kobe University, Kobe, Japan
Methods: DNA techniques, biological assays, radiolabeling, centrifugation, autoradiography
Expand this compound
Collapse this compound
11. Compound ID: 32622
|
/Variants 0/-+
|
-4)-a-D-GalpA-(1-
/Variants 0/ is:
b-L-Araf-(1-5)-b-D-3dlyxHepp-ulosaric-(2-3)-
OR (exclusively)
a-L-Rhap-(1-5)-Kdo-(2-3)-
OR (exclusively)
L-Fucp2Me-(1-2)-+
|
a-L-Rhap-(1-3)-+ |
| |
b-L-Araf-(1-2)-a-L-Rhap-(1-2)-a-L-Arap-(1-4)-a-D-Galp-(1-2)-b-AcefA-(1-3)-b-L-Rhap-(1-5)-b-D-Apif-(1-2)-
OR (exclusively)
a-D-GalpA-(1-2)-+
|
a-D-Xylp2Me-(1-3)-+ |
| |
Subst-(?-3)-a-D-Galp-(1-2)-b-D-GlcpA-(1-4)-a-L-Fucp-(1-4)-b-L-Rhap-(1-5)-b-D-Apif-(1-2)-
|
b-D-GalpA-(1-3)-+
Subst = unknown |
Show graphically |
Structure type: structural motif or average structure
Compound class: polysaccharide
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_130650,IEDB_136045,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142489,IEDB_144562,IEDB_151528,IEDB_152214,IEDB_153553,IEDB_174333,IEDB_190606,IEDB_225177,IEDB_423153,IEDB_885823,SB_154,SB_7,SB_86
The structure is contained in the following publication(s):
- Article ID: 12594
Perez S, Mazeau K, Herve du Penhoat C "The three-dimensional structures of the pectic polysaccharides" -
Plant Physiology and Biochemistry 38(1-2) (2000) 37-55
The application of molecular modelling methods to the realistic description of cell wall polysaccharides is described. In a first section, the basic principles and tools are presented; they provide a consistent description of the levels of structural organization of polysaccharides, from the basic monomeric components to the more complex assemblies of macromolecular chains and their interactions. The second section provides a comprehensive illustration which includes the application of these methods to the elucidation of the structural features of the plant cell wall polysaccharides, pectins. The ordered and disordered states of both the `smooth' and the `hairy' regions of the pectin components are described, along with a discussion of the role of some key structural moieties such as the degree of esterification or acetylation. The stereochemical and electrostatic requirements for ionic binding to the polysaccharide chain are also presented. In an effort to provide a more global view, a `canonical' structure of pectin has been constructed and described; it corresponds to a hypothetical model having a molecular mass of 50 kDa. The main structural features of rhamnogalacturonan II, which have been determined to date, are also reported.
molecular modelling, cell wall, nuclear magnetic resonance, arabinogalactan, pectins, rhamnogalacturonan, 3D-structure
Publication DOI: 10.1016/S0981-9428(00)00169-8Journal NLM ID: 9882449Publisher: Elsevier Science for Société Française De Physiologie Végétale
Correspondence: perez@cermav.cnrs.fr
Institutions: Centre de recherches sur les macromolécules végétales, CNRS (Laboratory affiliated with the Joseph Fourier University), Grenoble, France
Expand this compound
Collapse this compound
Total list of structure IDs on all result pages of the current query:
Total list of corresponding CSDB IDs (permanent record IDs):
Execution: 2 sec