Found 12 structures.
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1. Compound ID: 21989
Structure type: monomer
Trivial name: hyperoside, hyperin, hyperoside, hyperin, baohuoside-II, quercetin 3-galactoside, vulgarsaponin B
Compound class: saponin glycoside, glycoside, flavonoid glycoside, flavonol glycoside, flavone glycoside, flavanone glycoside
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- 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: 9200
Li Y, Li Y-S, Liu Y, Liu Y-L "Flavonol glycosides from Epimedium pubescens" -
Journal of Natural Products 53(5) (1990) 1337-1339
A novel flavonol glycoside, rouhuoside [l], was isolated from aerial parts of Epimedium pubescens along with six known flavonol glycosides. Structures were established by spectroscopic and chemical methods. The structure of rouhuoside [l] was elucidated as 8-prenylkaempferol-3-O-α-L-rhamnopyranosyl-(4→1)-β-D-glucopyranosyl-7-O-β-D-glucopyranoside. The known compounds were identified as epimedoside C, icariside I, icariin, baohuoside VI, hyperin, and baohuoside I
rouhuoside, flavonol glycoside, Epimedium pubescens
Publication DOI: 10.1021/np50071a030Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Institutions: Department of Phytochemistry, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Beijing, China
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, acid hydrolysis, UV, enzymatic digestion, extraction, CC, melting point determination, filtration
- Article ID: 9201
Li W-K, Pan J-Q, Lü M-J, Zhang R-Y, Xiao P-G "A 9,10-dihydrophenanthrene derivate from Epimedium koreanum" -
Phytochemistry 39(1) (1995) 231-233
A new 9,10-dihydrophenanthrene derivative named epimedoicarisoside A was isolated from the aerial parts of Epimedium koreanum along with ten known flavonoids. The structure of this compound was determined on the basis of spectral analysis (FAB-Mass spectrometry, 1H-1H COSY, 13C COSY, DEPT, and 13C long range COSY, etc.) as 2-hydroxy-3,4,6,7-tetramethoxy-9,10-dihydrophenanthrene-2-O-β-D-glucopyranoside. The known compounds were identified as icariin, epimedoside C, icarisid I, baohuoside I, diphylloside A, baohuoside II, 2″-O-rhamnosylicarisid II, sagittatoside A, hyperoside and icaritin-3-O-rhamnopyranoside.
flavonoids, Epimedium koreanum, Berberidaceae, 9, 10-dihydrophenanthrene derivate, epimedoicarisoside A, icariin, epimedoside C, icarisid I, baohuoside I, diphylloside A, baohuoside II, 2″-O-rhamnosylicarisid II, sagittatoside A, hyperoside, icaritin-3-O-rhamnopyranoside
Publication DOI: 10.1016/0031-9422(94)00926-KJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, China, Department of Chemistry, Peking University, Beijing, China, Department of Phytochemistry, School of Pharmaceutical Sciences, Beijing Medical University, Beijing, China
Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS, TLC, UV, extraction, CC, melting point determination, recrystallization
- Article ID: 10778
Rommel A, Wrolstad RE "Composition of flavonols in red raspberry juice as influenced by cultivar, processing, and environmental factors" -
Journal of Agricultural and Food Chemistry 41 (1993) 1941-1950
Flavonols were characterized and measured in experimental (n = 46) and commercial (n = 9) red raspberry juices by HPLC/diode array spectral techniques. Samples were prepared using minicolumns, packed with Polyamide 6. A fraction eluted with methanol contained eight or fewer quercetin glycosides, quercetin, and kaempferol. A second fraction eluted subsequently with 0.5% ammonia in methanol contained three flavonol glucuronides, two flavonol forms, aglycons, ellagic acid, and its derivatives. Quercetin 3-glucuronide was the major flavonol in experimental and commercial juices, respectively (mean of 54 and 51 ppm), and a flavonol presumed to be quercetin 3-sophoroside was the second primary compound (means of 29 and 33 ppm). In addition, 36 flavonol forms were measured in trace amounts. The mean total concentrations of quercetin and kaempferol forms, respectively, in experimental juices (n = 45) were 118 and 3.6 ppm and in commercial juices (n = 7) 121 and 3.4 ppm, respectively. The mean total flavonol concentrations in experimental and commercial juices were 122 and 125 ppm, respectively. Influences of cultivar (n = l0), processing method (standard, high-speed centrifugation, depectinization, diffusion extraction, vacuum and osmotic concentration) and environmental factors (geographic origin, maturity, harvesting method, mold contamination) were evaluated.
Publication DOI: 10.1021/jf00035a025Journal NLM ID: 0374755Publisher: American Chemical Society
Institutions: Department of Food Science and Technology, Wiegand Hall, Oregon State University, Corvallis, Oregon, USA
Methods: HPLC
- Article ID: 10913
Marco JA, Barbera O, Sanz J, Sanchez-Parareda J "Flavonol glycosides from Anthyllis onobrychioides" -
Phytochemistry 24 (1985) 2471-2472
A new flavonol glycoside, rhamnocitrin 3-O-β-D-galactopyranoside, has been isolated from aerial parts of Anthyllis onobrychioides, together with the known 3-O-β-D-galactopyranosides of quercetin, isorhamnetin and kaempferol.
structure elucidation, flavonoids, flavonol glycosides, Leguminosae, Anthyllis onobrychioides
Publication DOI: 10.1016/S0031-9422(00)83076-9Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Departamento de Químíca Orgánica, Facultad Químicas, Burjasot, Valencia, Spain
Methods: 13C NMR, 1H NMR, UV, CC, FD-MS, 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: 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: 11134
Rastrelli L, DeTommasi N, Berger I, Caceres A, Saravia A, DeSimone F "Glycolipids from Byrsonima crassifolia" -
Phytochemistry 45(4) (1997) 647-650
From the leaves of Byrsonima crassifolia four new glycolipids, 1,2-di-O-miristoyl-3-O-(6-sulpho-α-d-quinovopyranosyl)-glycerol, 1,2-di-O-(8-hexadecenoyl)-3-O-(6-sulpho-α-d-quinovopyranosyl)-glycerol, 1,2-di-O-palmitoyl-3-O-(β-d-glucopyranosyl)- glycerol and 1,2-di-O-(8-hexadecenoyl)-3-O-(β-d-glucopyranosyl)-glycerol, have been isolated. Nine known compounds were also found. The structures of new compounds were elucidated on the basis of chemical and spectral data.
glycolipids, leaves, Byrsonima crassifolia, Malpighiaceae, ‘nanche’, sulphonoglycolipids
Publication DOI: 10.1016/S0031-9422(96)00842-4Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Dipartimento di Scienze Farmaceutiche, Universitá di Salerno, Piazza V. Emanuele 9 84084, Penta di Fisciano, Italy
Methods: 13C NMR, 1H NMR, FAB-MS, GC-MS, sugar analysis, TLC, GC, chemical methods, alkaline hydrolysis, 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: 11650
Wang Z, Zhao Y, Tu G, Hong S, Chen Y "Studies on the chemical constituents from Prunella vulgaris" -
Yao xue xue bao = Acta pharmaceutica Sinica [Chinese] 34(9) (1999) 679-681
AIM: To find the chemical constituents of Prunella vulgaris L. METHODS: To separate the constituents of Prunella vulgaris by using various kinds of chromatography and identify their structures on the basis of spectral analysis. RESULTS: Six compounds were isolated from the spikes of Prunella vulgaris L. Their structures were established as 3β,16α,24-trihydroxyoleana-12-en-28-oic acid-3-O-(6′-butyryl)-β-D-glucopyranosid (I), ursolic acid (II), 2α,3α-dihydroxyurs-12-en-28-oic acid (III), quercetin (IV), quercetin-3-O-β-D-galactoside (V) and ethyl caffeate (VI) based on the analysis of spectral data of IR, UV FAB-MS, 1D and 2D-NMR. CONCLUSION: I was a new compound, named vulgarsaponin B, III was isolated for the first time from this plant, V and VI for the first time from the Prunella genus.
triterpenoid saponin, Labiate, Prunella vulgaris, vulgarsaponin B
Journal NLM ID: 21710340RWWW link: http://www.yxxb.com.cn:8081/aps/CN/abstract/abstract9158.shtmlPublisher: Beijing: Zhongguo yao xue hui
Correspondence: Chen Y
Institutions: Division of Natural Medicinal Chemistry, Beijing Medical University, Beijing, 100083, China, Beijing Institute of Microchemistry, Beijing 100083, China
Methods: 13C NMR, 1H NMR, IR, FAB-MS, UV, DEPT, HR-SI-MS
- Article ID: 11795
Chevalley I, Marston A, Hostettmann K "A new gallic acid fructose ester from Saxifraga stellaris" -
Phytochemistry 50(1) (1999) 151-154
Seven compounds have been isolated from methanol extracts of whole Saxifraga stellaris (Saxifragaceae) plants. They were identified as the new compound, 6-O-galloyl fructose, together with 3-O-[2-O-(β-D-xylopyranosyl)-β-D-galactopyranosyl]-kaempferol, 3-O-[2-O-(β-D-xylopyranosyl)-β-D-galactopyranosyl]-quercetin, trifolin, hyperin, resveratrol-3-O-glucoside, triandrin, by chemical and spectroscopic methods. Their free radical scavenging properties are also described.
fructose, flavonoid glycosides, free radical scavengers, Saxifragaceae, Saxifraga stellaris, stilbene glycoside, 6-O-galloyl, triandrin
Publication DOI: 10.1016/S0031-9422(98)00496-8Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Institut de Pharmacognosie et Phytochimie, Université de Lausanne, BEP, CH-1015 Lausanne, Switzerland
Methods: 13C NMR, 1H NMR, EI-MS, TLC, HPLC, alkaline hydrolysis, UV, optical rotation measurement, DCI-MS, antioxidant activities, HMBC, DEPT, COSY, HSQC
- 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: 11876
Calis I, Kuruüzüm A, Demirezer LO, Sticher O, Ganci W, Rüedi P "Phenylvaleric acid and flavonoid glycosides from Polygonum salicifolium" -
Journal of Natural Products 62(8) (1999) 1101-1105
(3R)-O-β-D-Glucopyranosyloxy-5-phenylvaleric acid (1), (3R)-O-β-D-glucopyranosyloxy-5-phenylvaleric acid n-butyl ester (2), and a new dihydrochalcone diglycoside 4'-O-[β-D-glucopyranosyl-(1→-6)-glucopyranosyl]-oxy-2'-hydroxy-3',6'-dimethoxydihydrochalcone (3), together with six known flavonoid glycosides [kaempferol-3-O-β-D-glucopyranoside (= astragalin) (4), kaempferol-3-O-β-D-galactopyranoside (5), quercetin-3-O-β-D-glucopyranoside (= isoquercitrin) (6), quercetin-3-O-β-D-galactopyranoside (= hyperoside) (7), quercetin-3-O-(2'-O-galloyl)-β-D-glucopyranoside (8), and quercetin-3-O-β-D-glucuronopyranoside (9)] were isolated from the aerial parts of Polygonum salicifolium. The structure elucidation of the isolated compounds was performed by spectroscopic (UV, IR, ESI-MS, 1D- and 2D-NMR), chemical (methylation, enzymatic hydrolysis, partial synthesis), and chromatographic methods (HPLC, Chiralcel OD). The flavonoid glycosides (4-9) demonstrated scavenging properties toward the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical in TLC autographic assays.
isoquercitrin, hyperoside, flavonoid glycoside, phenylvaleric acid glycoside, Polygonum salicifolium, astragalin
NCBI PubMed ID: 10479312Publication DOI: 10.1021/np9900674Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: Calis I
Institutions: Hacettepe University, Faculty of Pharmacy, Department of Pharmacognosy, TR-061000 Ankara, Turkey, Swiss Federal Institute of Technology (ETH) Zurich, Department of Pharmacy, CH-8057 Zurich, Switzerland, University of Zurich, Institute of Organic Chemistry, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland
Methods: 13C NMR, 1H NMR, methylation, IR, FAB-MS, TLC, enzymatic hydrolysis, ESI-MS, HPLC, UV, optical rotation measurement, ROESY, reduction with NaBH4, antioxidant activities, HMBC, HMQC, DEPT, COSY, MPLC, hydrogenation, DFQ-COSY
- 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: 12080
Lei H, Wei L, Lin W "Chemical constituents of Geranium dahuricum DC" -
Yao xue xue bao = Acta pharmaceutica Sinica [Chinese] 35(1) (2000) 67-69
Components were separated by means of solvent extraction and chromatography on Toyopeal and Sephadex LH20, the structures were determined by spectral analysis and chemical evidences. Five compounds were obtained and elucidated as methyl-3-O-(β-D-glucopyranosyl)-gallate (I), methyl-3-O-[β-D-(6′-O-galloyl)-glucopyranosyl]-gallate (II), quercetin 3-O-β-D-galactopyranoside (III), myricetin 3-O-β-D-galactopyranoside (IV), myricetin 3-O-α-L-rhamnopyranoside (V). These compounds were separated from this plant for the first time, where I and II were new natural products.
quercetin, myricetin, Geranium dahuricum DC, methyl gallate
Journal NLM ID: 21710340RPublisher: Beijing: Zhongguo yao xue hui
Methods: 13C NMR, 1H NMR, IR, FAB-MS, extraction, CC, melting point determination
- 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: 12174
Foo LY, Lu Y, Molan AL, Woodfield DR, McNabb WC "The phenols and prodelphinidins of white clover flowers" -
Phytochemistry 54(5) (2000) 539-548
White clover flowers (Trifolium repens L.) contain an abundance of phenolics, namely cis- and trans-p-coumaric acid 4-O-β-D-glucopyranoside, the 3-O-β-D-galactopyranosides of myricetin, quercetin and kaempferol together with two new derivatives namely myricetin 3-O-(6"-acetyl)-β-D-galactopyranoside and kaempferol 3-O-(6"-acetyl)-β-D-galactopyranoside. Gallocatechin, epigallocatechin, gallocatechin-(4α-8)-epigallocatechin and their corresponding prodelphinidin polymers were also present. The 13C-NMR spectra showed that the polymers consisted of only gallocatechin and epigallocatechin monomeric units with the latter being about twice as abundant in the extenders but only slightly more than that in the terminating units. The average degree of polymerization was estimated by 13C-NMR and ES-MS, which gave a remarkably consistent result of about 5.8 flavanol units.
phenolics, Leguminosae, flowers, Trifolium repens, prodelphinidins, molecular size
NCBI PubMed ID: 10939359Publication DOI: 10.1016/s0031-9422(00)00124-2Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: y.foo@irl.cri.nz
Institutions: Industrial Research, Lower Hutt, New Zealand, Ag Research, Grassland Research Centre, Palmerston North, New Zealand
Methods: 13C NMR, 1H NMR, NMR-2D, ESI-MS, acid hydrolysis, HPLC, extraction, CC, evaporation
- 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
- 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: 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: 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: 12326
Kunert O, Haslinger E, Schmid MG, Reiner J, Bucar F, Mulatu E, Abebe D, Debella A "Three saponins, a steroid, and a flavanol glycoside from Achyrantes aspera" -
Monatshefte für Chemie 131(2) (2000) 195-204
Three bisdesmosidic saponins, 20-hydroxyecdysone, and quercetin-3-O-β-D-galactoside were isolated from the methanol extract of the aerial parts of Achyranthes aspera L. (Amaranthaceae). Their structures were established on the basis of NMR spectroscopic analysis; the complete 1H and 13C assignments of the compounds were achieved by means of 2D NMR studies.
NMR spectroscopy, structure elucidation, natural products, saponins
Publication DOI: 10.1007/PL00010306Journal NLM ID: 0254164Publisher: Wien, New York: Springer-Verlag
Institutions: Institut für Pharmazeutische Chemie, Universität Graz, Graz, Austria, Ethiopian Health and Nutrition Research Institute, Addis Ababa, Ethiopia, Institut für Pharmakognosie, Universität Graz, Graz, Austria, Laboratory for Organic Chemistry I, University of Bayreuth, Bayreuth, Germany
- 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: 12335
Lamidi M, Rondi ML, Ollivier E, Faure R, Nze Ekekang L, Balansard G "Constituents of Ipomoea fistulosa leaves" -
Fitoterapia 71(2) (2000) 203-204
The isolation of flavonol glycosides 1-3 from the leaves of Ipomoea fistulosa is reported.
flavonols, Ipomoea fistulosa
NCBI PubMed ID: 10727823Publication DOI: 10.1016/s0367-326x(99)00147-1Journal NLM ID: 16930290RPublisher: Elsevier
Correspondence: guy.balansard@pharmacie.univ-mrs.fr
Institutions: IPHAMETRA (CENAREST) BP 842, Libreville, Gabon, FMSS BP 6087, Libreville, Gabon, Laboratory of Pharmacognosy, Faculty of Pharmacy, Marseille, France, URA 1411 Université d’Aix-Marseille III, Marseille, France
- Article ID: 12378
Itoh A, Tanahashi T, Ikejima (née Sato) S, Inoue M, Nagakura N, Inoue K, Kuwajima H, Wu HX "Five phenolic glycosides from Alangium chinense" -
Journal of Natural Products 63(1) (2000) 95-98
From the dried leaves of Alangium chinense, five novel phenolic glycosides, 6‘-O-galloylsalicin (1); 4‘,6‘-di-O-galloylsalicin (2); 4‘,6‘-O-(S)-hexahydroxydiphenoylsalicin (3); 4‘,6‘-O-(R)-hexahydroxydiphenoylsalicin (4); and pyrocatechol 1-O-β-d-xylopyranosyl(1→6)-β-d-glucopyranoside (5) were isolated. The structures of these new compounds were determined by spectroscopic methods.
phenolic glycosides, gallic acid, Alangium chinense, salicins
NCBI PubMed ID: 10650086Publication DOI: 10.1021/np990391zJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: tanahash@kobepharma-u.ac.jp
Institutions: Kobe Pharmaceutical University, Kobe, Japan, Gifu Pharmaceutical University, Mitahora-higashi, Japan, Faculty of Pharmaceutical Sciences, Kinki University, Higashiosaka, Japan, Yunnan Pharmaceutical Group Corporation, Kunming, China
Methods: 13C NMR, 1H NMR, deacetylation, NMR-2D, IR, HPLC, UV, extraction, optical rotation measurement, CD, CC, melting point determination, evaporation, SI-MS, RP-MPLC, PTLC, HR-SI-MS
- 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: 12380
Iwashina T, Kitajima J "Chalcone and flavonol glycosides from Asarum canadense (Aristolochiaceae)" -
Phytochemistry 55(8) (2000) 971-974
Two chalcone glycosides were isolated, together with seven known flavonol glycosides, from the leaves of Asarum canadense. The structures of the chalcone glycosides were established as chalcononaringenin 2',4'-di-O-glucoside and chalcononaringenin 2'-O-glucoside-4'-O-gentiobioside by chemical, UV, FAB MS, 1H and 13C NMR evidence.
Aristolochiaceae, Asarum canadense, chalcononaringenin 2', 4'-di-O-glucoside, chalcononaringenin 2'-O-glucoside-4'-O-gentiobioside
NCBI PubMed ID: 11140534Publication DOI: 10.1016/s0031-9422(00)00216-8Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: iwashina@kahaku.go.jp
Institutions: Tsukuba Botanical Garden, National Science Museum, Tsukuba, Japan, Laboratory of Pharmacognosy, Showa College of Pharmaceutical Science, Machida, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, UV, extraction, CC, preparative paper chromatography, evaporation, HR-FAB-MS
- Article ID: 12405
Lin LZ, He XG, Lindenmaier M, Yang J, Cleary M, Qiu SX, Cordell GA "LC-ESI-MS study of the flavonoid glycoside malonates of red clover (Trifolium pratense)" -
Journal of Agricultural and Food Chemistry 48(2) (2000) 354-365
High-performance liquid chromatography−electrospray ionization−mass spectrometry (LC-ESI-MS) was applied to the analysis of the flavonoids and their glycoside malonates of the flowers and leaves of red clover (Trifolium pratense). Through LC-MS comparative studies on the plant extracts and their malonate-free extracts, ∼20 flavonoid glycoside malonates were detected in the flower extract. Eight were identified as genistin 6‘‘-O-malonate (39), formononetin 7-O-β-D-glucoside 6‘‘-O-malonate (40), biochanin A 7-O-β-D-glucoside 6‘‘-O-malonate (41), trifoside 6‘‘-O-malonate (42), irilone 4‘-O-β-D-glucoside 6‘‘-O-malonate (43), pratensein 7-O-β-D-glucoside 6‘‘-O-malonate (44), isoquercitrin 6‘‘-O-malonate (45), and 3-methylquercetin 7-O-β-D-glucoside 6‘‘-O-malonate (46). About 15 other flavonoids and clovamides were proved to be present in this extract. The study also found that the flowers contained flavones as the major flavonoids, whereas the leaves had isoflavones as the major flavonoids. This is the first detection of the six malonates (39 and 42−46) in the extracts of red clover, and among them, 42, 43, and 46 are new compounds.
flavonoids, Leguminosae, Trifolium pratense, red clover, flavonoid glycoside malonates, clovamides, LC-ESI-MS analysis
NCBI PubMed ID: 10691640Publication DOI: 10.1021/jf991002+Journal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: longze.lin@amtbotanicals.com
Institutions: Research Laboratory of Natural Products Chemistry, A. M. Todd Botanicals, Eugene, USA, Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, The University of Illinois at Chicago, Chicago, IL, USA
Methods: LC-ESI-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: 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: 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: 12634
Sakushima A, Nishibe S, Hisada S "Studies on the constituents of Apocynaceae plants. Isolation of flavonol glycosides and other components from the leaves of Apocynum venetum L. var. basikurumon Hara" -
Yakugaku Zasshi = Journal of the Pharmaceutical Society of Japan [Japanese] 98(10) (1978) 1395-1397
From the methanolic extract of leaves of Apocynum venetum L. var. basikurumon HARA, eight constituents were isolated and identified with respective authentic samples as succinic acid, chlorogenic acid, isoquercitrin, hyperoside, D-(-)-bornesitol, sucrose, β-sitosterol, and β-amyrin.
NCBI PubMed ID: 745047Publication DOI: 10.1248/yakushi1947.98.10_1395Journal NLM ID: 0413613Publisher: Tokyo: Nihon Yakugakkai
Institutions: Faculty of Pharmaceutical Sciences, Higashi Nippon Gakuen University, Ishikari-Tobetsu, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, extraction, optical rotation measurement, CC, centrifugation
- 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: 12705
Smith GJ, Thomsen SJ, Markham KR, Andary C, Cardon D "The photostabilities of naturally occurring 5-hydroxyflavones, flavonols, their glycosides and their aluminium complexes" -
Journal of Photochemistry and Photobiology. A, Chemistry 136(1-2) (2000) 87-91
The photostabilities of luteolin, in solution, in the presence of aluminium ions, and deposited on a cellulosic substrate have been determined and compared with those of quercetin and other 5-hydroxyflavonols and their 3-O-glycosides. In aqueous methanol solution, luteolin and flavonol 3-glycosides exhibited no degradation over periods of up to 15 h of UV irradiation. However, the flavonols studied were all found to degrade and their relative photostabilities correlate with their redox potentials. Quercetin was the least stable. In the presence of aluminium ions, all the flavonoids, including luteolin, were degraded by UV irradiation. In contrast to the absorption spectra in dilute solution, the reflectance spectra of both quercetin and luteolin deposited on a cellulosic substrate exhibited strong absorptions beyond 400 nm. On this substrate these flavonoids displayed the characteristic yellow colour associated with flavonoids in some environments. Although the quercetin yellow faded rapidly on exposure to UV radiation, the colour of luteolin darkened. This was due to the formation of a photoproduct absorbing maximally at 450 nm. The relevance of these observations to cellulosic dyeing and flower colouration are discussed.
5-hydroxyflavones; flavonols; luteolin; quercetin
Publication DOI: 10.1016/S1010-6030(00)00320-8Journal NLM ID: 9883240Publisher: Lausanne, Switzerland: Elsevier Sequoia
Institutions: New Zealand Institute for Industrial Research, Lower Hutt, New Zealand, Laboratoire de Botanique, Phytochimie et Mycologie, Université Montpellier 1, Montpellier, France, CNRS, Lyon, France
Methods: UV, spectrophotometry
- 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: 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: 12837
Xiong Q, Fan W, Tezuka Y, Adnyana IK, Stampoulis P, Hattori M, Namba T, Kadota S "Hepatoprotective effect of Apocynum venetum and its active constituents" -
Planta Medica 66(2) (2000) 127-133
The leaves of Apocynum venetum L. are used as a tea material in north China and Japan. A water extract (500 mg/kg/day, one week administration) of the leaves of A. venetum showed protective effects against carbon tetrachloride (CCl4, 30 μl/mouse) or D-galactosamine (D-GalN, 700 mg/kg)/lipopolysaccharide (LPS, 20 μg/kg)-induced liver injury in mice. Tumor necrosis factor-α (TNF-α) secreted from LPS-stimulated macrophages is the most crucial mediator in the D-GalN/LPS-induced liver injury model. The extract had no significant inhibition on the increase of serum TNF-α (1169 ± 132 pg/ml vs. 1595 ± 314 pg/ml of control), but exhibited a complete inhibition at the concentration of 100 micrograms/ml on TNF-α (100 ng/ml)-induced cell death in D-GalN (0.5 mM)-sensitized mouse hepatocytes. Further activity-guided fractionation resulted in the isolation of fifteen flavonoids viz. (-)-epicatechin (1), (-)-epigallocatechin (2), isoquercetin (3), hyperin (4), (+)-catechin (5), (+)-gallocatechin (6), kaempferol-6'-O-acetate (7), isoquercetin-6'-O-acetate (8), catechin-[8,7-e]-4 α-(3,4-dihydroxpyhenyl)-dihydro-2(3H)-pyranone (9), apocynin B (10), apocynin A (11), cinchonain Ia (12), apocynin C (13), apocynin D (14) and quercetin (15). All the compounds showed inhibitory effects on TNF-α-induced cell death with different intensities. The flavonol glycosides 3, 4, 7 and 8 and the phenylpropanoid-substituted flavan-3-ols 11 and 12 showed potent inhibitory effects on TNF-α-induced cell death with IC50 values of 37.5, 14.5, 31.2, 55.1, 71.9 and 41.2 μM, respectively. In contrast, the clinically used 5 and its analogues 1, 2 and 6 showed apparent activity only at 80 microM. These flavonoids appeared to be the hepatoprotective principles of the leaves of A. venetum. The hepatoprotective effects exhibited by the extract and its constituents suggest a validation of the leaves as a tea material.
hepatoprotective activity, liver injury, Apocynum venetum
NCBI PubMed ID: 10763585Publication DOI: 10.1055/s-2000-11135Journal NLM ID: 0066751Publisher: George Thieme
Correspondence: kadota@ms.toyama-mpu.ac.jp
Institutions: Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, Toyama, Japan
Methods: biological assays, extraction, optical rotation measurement, PTLC
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2. Compound ID: 23927
|
a-L-Rhap-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-3)-Subst
Subst = olean-12-en-3β,28-diol = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)CC[C@@]({28}CO)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Trivial name: rivularinin
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9818
Seshadri V, Batta AK, Rangaswami S "Structure of two new saponins from Achyranthes aspera" -
Indian Journal of Chemistry 20 (1981) 773-775
- Article ID: 9913
Hariharan V, Rangaswami S "Structure of saponins A and B from the seeds of Achyranthes aspera" -
Phytochemistry 9 (1970) 409-414
The structure of Achyranthes saponin A has been established as α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→4)-β-D-glucuronopyranosyl(1→3)-oleanolic acid (VI) and that of saponin B as the β-D-galactopyranosyl (1→28) ester of saponin a (VII).
Publication DOI: 10.1016/S0031-9422(00)85154-7Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Chemistry, University of Delhi, Delhi, India
Methods: acid hydrolysis, methylation analysis, PC
- Article ID: 9926
Tiwari KP, Singh RB "Rivularinin, a new saponin from Anemone rivularis" -
Phytochemistry 17 (1978) 1991-1994
A new saponin, rivularinin, has been isolated from the ethanolic extract of Anemone rivularis (Ranunculaceae). The saponin was shown to be [α-l-arabinofuranosyl(1→2)-α-l-rhamnopyranosyl(1→4)-β-d-glucopyranosyl(1→4)-β-d-glucuronopyranosyl(1→3)]-3β-hydroxy-olean-12-en-28-oic acid.
structural determination, Ranunculaceae, Anemone rivularis, rivularinin, [α-l-arabinofuranosyl(1→2)-α-l-rhamnopyranosyl(1→4)-β-d-glucopyranosyl(1→4)-β-d-glucuronopyranosyl(1→3)]-3β-hydroxy-olean-12-en-28-oic acid
Publication DOI: 10.1016/S0031-9422(00)88749-XJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Chemistry, University of Allahabad, Allahabad, India
Methods: periodate oxidation, IR, partial acid hydrolysis, TLC, acid hydrolysis, MS, permethylation, PMR
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3. Compound ID: 23928
|
a-L-Rhap-(1-4)-b-D-Glcp-(1-4)-b-D-GlcpA6Me-(1-3)-Oleanolic
Oleanolic = 3β-hydroxyolean-12-en-28-oic acid |
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Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136105,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9818
Seshadri V, Batta AK, Rangaswami S "Structure of two new saponins from Achyranthes aspera" -
Indian Journal of Chemistry 20 (1981) 773-775
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4. Compound ID: 23929
|
b-D-Glcp-(1-28)-+
|
a-L-Rhap-(1-4)-b-D-Glcp-(1-4)-b-D-GlcpA6Me-(1-3)-Oleanolic
Oleanolic = 3β-hydroxyolean-12-en-28-oic acid |
Show graphically |
Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136105,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9818
Seshadri V, Batta AK, Rangaswami S "Structure of two new saponins from Achyranthes aspera" -
Indian Journal of Chemistry 20 (1981) 773-775
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5. Compound ID: 23930
|
b-D-Glcp-(1-28)-+
|
a-L-Rhap-(1-4)-b-D-Glcp-(1-4)-b-D-GlcpA-(1-3)-Oleanolic
Oleanolic = 3β-hydroxyolean-12-en-28-oic acid |
Show graphically |
Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136105,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9818
Seshadri V, Batta AK, Rangaswami S "Structure of two new saponins from Achyranthes aspera" -
Indian Journal of Chemistry 20 (1981) 773-775
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6. Compound ID: 24086
|
a-L-Rhap-(1-4)-b-D-Glcp-(1-4)-b-D-GlcpA-(1-3)-Oleanolic
Oleanolic = 3β-hydroxyolean-12-en-28-oic acid |
Show graphically |
Structure type: oligomer
Trivial name: rivularinin
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136105,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9913
Hariharan V, Rangaswami S "Structure of saponins A and B from the seeds of Achyranthes aspera" -
Phytochemistry 9 (1970) 409-414
The structure of Achyranthes saponin A has been established as α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→4)-β-D-glucuronopyranosyl(1→3)-oleanolic acid (VI) and that of saponin B as the β-D-galactopyranosyl (1→28) ester of saponin a (VII).
Publication DOI: 10.1016/S0031-9422(00)85154-7Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Chemistry, University of Delhi, Delhi, India
Methods: acid hydrolysis, methylation analysis, PC
- Article ID: 9926
Tiwari KP, Singh RB "Rivularinin, a new saponin from Anemone rivularis" -
Phytochemistry 17 (1978) 1991-1994
A new saponin, rivularinin, has been isolated from the ethanolic extract of Anemone rivularis (Ranunculaceae). The saponin was shown to be [α-l-arabinofuranosyl(1→2)-α-l-rhamnopyranosyl(1→4)-β-d-glucopyranosyl(1→4)-β-d-glucuronopyranosyl(1→3)]-3β-hydroxy-olean-12-en-28-oic acid.
structural determination, Ranunculaceae, Anemone rivularis, rivularinin, [α-l-arabinofuranosyl(1→2)-α-l-rhamnopyranosyl(1→4)-β-d-glucopyranosyl(1→4)-β-d-glucuronopyranosyl(1→3)]-3β-hydroxy-olean-12-en-28-oic acid
Publication DOI: 10.1016/S0031-9422(00)88749-XJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Chemistry, University of Allahabad, Allahabad, India
Methods: periodate oxidation, IR, partial acid hydrolysis, TLC, acid hydrolysis, MS, permethylation, PMR
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7. Compound ID: 24087
|
b-D-Galp-(1-28)-+
|
a-L-Rhap-(1-4)-b-D-Glcp-(1-4)-b-D-GlcpA-(1-3)-Oleanolic
Oleanolic = 3β-hydroxyolean-12-en-28-oic acid |
Show graphically |
Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_190606,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 9913
Hariharan V, Rangaswami S "Structure of saponins A and B from the seeds of Achyranthes aspera" -
Phytochemistry 9 (1970) 409-414
The structure of Achyranthes saponin A has been established as α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→4)-β-D-glucuronopyranosyl(1→3)-oleanolic acid (VI) and that of saponin B as the β-D-galactopyranosyl (1→28) ester of saponin a (VII).
Publication DOI: 10.1016/S0031-9422(00)85154-7Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Chemistry, University of Delhi, Delhi, India
Methods: acid hydrolysis, methylation analysis, PC
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8. Compound ID: 30423
Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside, flavonol glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136105,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 11783
Park SH, Oh SR, Jung KY, Lee IS, Ahn KS, Kim JG, Lee JJ, Lee HK "Anticomplement activities of oleanolic acid monodesmosides and bisdesmosides isolated from Tiarella polyphylla" -
Archives of Pharmacal Research 22(4) (1999) 428-431
Seven known oleanolic acid glycosides (1-7) were isolated from the MeOH extract of Tiarella polyphylla. The structures were identified to be 3-O-(β-D-glucopyranosyl) oleanolic acid (1), 3-O-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl] oleanolic acid (2), 3-O-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl] oleanolic acid (3), 3-O-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl] oleanolic acid 28-O-β-D-glucopyranosyl ester (4), 3-O-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl] oleanolic acid 28-O-β-D-glucopyranosyl ester (5), 3-O-[a-L-rhamnopyranosyl-(1→3)-β-D-glucuronopyranosyl] oleanolic acid (6), and 3-O-[α-L-rhamnopyranosyl-(1→3)-β-D-glucuronopyranosyl] oleanolic acid 28-O-β-D-glucopyranosyl ester (7) on the basis of physicochemical and spectral data. These triterpene glycosides were tested for the anticomplement activity and hemolytic activity. Bisdesmosidic saponins, 4, 5, and 7, showed anticomplement activity; in contrast, monodesmosidic saponins, 1-3, and 6, showed direct hemolytic activity. Methyl esterified monodesmosidic saponins showed anticomplement activity at a low concentration and hemolytic activity at a high concentration.
saponins, Tiarella polyphylla, Saxifragaceae, anti-complement activity, hemolytic activity
NCBI PubMed ID: 10489887Publication DOI: 10.1007/BF02979071Journal NLM ID: 8000036Publisher: Pharmaceutical Society of Korea
Correspondence: Lee HK
Institutions: Natural Product Biosynthesis Research Unit, Korea Research Institute of Bioscience & Biotechnology, Yusong, P. O. Box 115, 305-600, Taejeon, South Korea, nstitute of Natural Drug Resources, 360-060, Cheongju, Korea
Methods: 13C NMR, 1H NMR, methylation, TLC, hemolytic activity, HCl hydrolysis, anti-complement activity
- Article ID: 12326
Kunert O, Haslinger E, Schmid MG, Reiner J, Bucar F, Mulatu E, Abebe D, Debella A "Three saponins, a steroid, and a flavanol glycoside from Achyrantes aspera" -
Monatshefte für Chemie 131(2) (2000) 195-204
Three bisdesmosidic saponins, 20-hydroxyecdysone, and quercetin-3-O-β-D-galactoside were isolated from the methanol extract of the aerial parts of Achyranthes aspera L. (Amaranthaceae). Their structures were established on the basis of NMR spectroscopic analysis; the complete 1H and 13C assignments of the compounds were achieved by means of 2D NMR studies.
NMR spectroscopy, structure elucidation, natural products, saponins
Publication DOI: 10.1007/PL00010306Journal NLM ID: 0254164Publisher: Wien, New York: Springer-Verlag
Institutions: Institut für Pharmazeutische Chemie, Universität Graz, Graz, Austria, Ethiopian Health and Nutrition Research Institute, Addis Ababa, Ethiopia, Institut für Pharmakognosie, Universität Graz, Graz, Austria, Laboratory for Organic Chemistry I, University of Bayreuth, Bayreuth, Germany
- Article ID: 12480
Michl G, Abebe D, Bucar F, Debella A, Kunert O, Schmid MG, Mulatu E, Haslinger E "New triterpenoid saponins from Achyrantes aspera Linn." -
Helvetica Chimica Acta 83(2) (2000) 359-363
Two new bisdesmosidic triterpenoid saponins, i.e. 1 and 2, were isolated, besides the three known saponins 3–5, from the MeOH extract of the aerial parts of Achyranthes aspera Linn. (Amaranthaceae). Their structures were elucidated as β-D-glucopyranosyl 3β-[O-α-L-rhamnopyranosyl-(1→3)-O-β-D-glucopyranuronosyloxy]machaerinate (1) and β-D-glucopyranosyl 3β-[O-β-D-galactopyranosyl-(1→2)-O-α-D-glucopyranuronosyloxy]machaerinate (2) by NMR spectroscopy, including 2D-NMR experiments (machaerinic acid=3β,21β-dihydroxyolean-12-en-28-oic acid). The other saponins were identified as β-D-glucopyranosyl 3β[O-α-L-rhamnopyranosyl-(1→3)-O-β-D-glucopyranuronosyloxy]oleanolate (3), β-D-glucopyranosyl 3-β-[O-β-D-galactopyranosyl-(1→2)-O-β-D-glucopyranuronosyloxy]oleanolate (4), and β-D-glucopyranosyl 3β-[O-β-D-glucopyranuronosyloxy]oleanolate (5) (oleanolic acid=3β-hydroxyolean-12-en-28-oic acid).
oleanolic acid, triterpenoid saponins, machaerinic acid, Achyranthes aspera
Publication DOI: 10.1002/(SICI)1522-2675(20000216)83:2<359::AID-HLCA359>3.0.CO;2-7Journal NLM ID: 2985094RPublisher: Verlag Helvetica Chimica Acta
Institutions: Institut für Pharmazeutische Chemie, Universität Graz, Graz, Austria, Ethiopian Health and Nutrition Research Institute, Addis Ababa, Ethiopia, Institut für Pharmakognosie, Universität Graz, Graz, Austria, Schering A.G. Berlin, Berlin, Germany
Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, TLC, HPLC, extraction, evaporation, centrifugation, HR-EI-MS
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9. Compound ID: 31534
Structure type: oligomer
Trivial name: chikusetsusaponin IVa, chikusetsusaponin-IVa
Compound class: glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_423153,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 12129
De Rosa S, Iodice C, Mitova M, Handjieva N, Popov S, Anchev M "Triterpene saponins and iridoid glucosides from Galium rivale" -
Phytochemistry 54(8) (2000) 751-756
Three new glycosides of the oleanene-type triterpenes, rivalosides C-E (1-3), along with three known triterpene saponins, momordin IIb (4) and rivalosides A-B (5-6), and five known iridoid glucosides: monotropein, scandoside, deacetylasperulosidic acid, geniposidic acid and asperulosidic acid, were isolated from aerial parts of Galium rivale. The structures of the new compounds were elucidated by spectral methods and chemical means as 2α-acetoxy-3α,19α-dihydroxy-olean-12-en-28-oic acid 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside, 2α,3α,19α-trihydroxy-olean-12-en-28-oic acid 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside and 3-O-β-D-glucuronopyranosyl-24-hydroxy-olean-12-en-28-oic acid 28-O-β-D-glucopyranoside, for rivalosides C-E, respectively. The taxonomic significance of the rivalosides in G. rivale was discussed.
triterpene saponin, Rubiaceae, iridoid glycoside, Galium rivale, rivalosides C-E
NCBI PubMed ID: 11014260Publication DOI: 10.1016/s0031-9422(00)00149-7Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: sderosa@icmib.na.cnr.it
Institutions: Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria, Institute of Botany, Bulgarian Academy of Sciences, Sofia, Bulgaria, Istituto per la Chimica di Molecole di Interesse Biologico del CNR, Napoli, Italy
Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS, TLC, acid hydrolysis, GC, alkaline hydrolysis, extraction, optical rotation measurement, acetylation, reduction, melting point determination, LPLC, DCCC
- Article ID: 12181
Fukuda N, Tanaka H, Shoyama Y "Applications of ELISA, Western blotting and immunoaffinity concentration for survey of ginsenosides in crude drugs of Panax species and traditional Chinese herbal medicines" -
The Analyst 125(8) (2000) 1425-1429
A combination of ELISA, Western blotting and immunoaffinity concentration using an anti-ginsenoside Rb1 monoclonal antibody was applied for qualitative and quantitative surveys of ginsenoside Rb1 and related ginsenosides in roots and traditional Chinese herbal medicines. To improve the low correlation between ELISA and HPLC analysis, the crude extract of roots was immunoaffinity concentrated to make evident the effect of malonyl ginsenoside Rb1. Immunoaffinity column chromatography also concentrated an unknown ginsenoside which had the same cross-reaction with ginsenoside Rb1.
antibody, ELISA, ginsenosides, ginseng, immunoaffinity chromatography
NCBI PubMed ID: 11002925Publication DOI: 10.1039/b002932gJournal NLM ID: 0372652Publisher: Cambridge: Royal Society of Chemistry
Correspondence: shoyama@shoyaku.phar.kyushu-u.ac.jp
Institutions: Department of Pharmacognosy, Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan
Methods: TLC, ELISA, Western blotting, HPLC, extraction, CC, evaporation, sonication, immunoaffinity chromatography
- Article ID: 12326
Kunert O, Haslinger E, Schmid MG, Reiner J, Bucar F, Mulatu E, Abebe D, Debella A "Three saponins, a steroid, and a flavanol glycoside from Achyrantes aspera" -
Monatshefte für Chemie 131(2) (2000) 195-204
Three bisdesmosidic saponins, 20-hydroxyecdysone, and quercetin-3-O-β-D-galactoside were isolated from the methanol extract of the aerial parts of Achyranthes aspera L. (Amaranthaceae). Their structures were established on the basis of NMR spectroscopic analysis; the complete 1H and 13C assignments of the compounds were achieved by means of 2D NMR studies.
NMR spectroscopy, structure elucidation, natural products, saponins
Publication DOI: 10.1007/PL00010306Journal NLM ID: 0254164Publisher: Wien, New York: Springer-Verlag
Institutions: Institut für Pharmazeutische Chemie, Universität Graz, Graz, Austria, Ethiopian Health and Nutrition Research Institute, Addis Ababa, Ethiopia, Institut für Pharmakognosie, Universität Graz, Graz, Austria, Laboratory for Organic Chemistry I, University of Bayreuth, Bayreuth, Germany
- Article ID: 12339
Lavaud C, Voutquenne L, Bal P, Pouny I "Saponins from Chenopodium album" -
Fitoterapia 71(3) (2000) 338-340
The isolation and spectral data of three saponins from the roots of Chenopodium album L. are reported. One of them is a seco-glycoside analogous to compounds that were previously found in species belonging to Caryophyllales.
Chenopodium album, triterpenoids, saponins, seco-glycosides
NCBI PubMed ID: 10844177Publication DOI: 10.1016/s0367-326x(99)00166-5Journal NLM ID: 16930290RPublisher: Elsevier
Institutions: Laboratoire de Pharmacognosie, UPRESA 6013, Faculté de Pharmacie, Reims, France, Institut Pierre Fabre, CRSN, Ramonville, France
- Article ID: 12480
Michl G, Abebe D, Bucar F, Debella A, Kunert O, Schmid MG, Mulatu E, Haslinger E "New triterpenoid saponins from Achyrantes aspera Linn." -
Helvetica Chimica Acta 83(2) (2000) 359-363
Two new bisdesmosidic triterpenoid saponins, i.e. 1 and 2, were isolated, besides the three known saponins 3–5, from the MeOH extract of the aerial parts of Achyranthes aspera Linn. (Amaranthaceae). Their structures were elucidated as β-D-glucopyranosyl 3β-[O-α-L-rhamnopyranosyl-(1→3)-O-β-D-glucopyranuronosyloxy]machaerinate (1) and β-D-glucopyranosyl 3β-[O-β-D-galactopyranosyl-(1→2)-O-α-D-glucopyranuronosyloxy]machaerinate (2) by NMR spectroscopy, including 2D-NMR experiments (machaerinic acid=3β,21β-dihydroxyolean-12-en-28-oic acid). The other saponins were identified as β-D-glucopyranosyl 3β[O-α-L-rhamnopyranosyl-(1→3)-O-β-D-glucopyranuronosyloxy]oleanolate (3), β-D-glucopyranosyl 3-β-[O-β-D-galactopyranosyl-(1→2)-O-β-D-glucopyranuronosyloxy]oleanolate (4), and β-D-glucopyranosyl 3β-[O-β-D-glucopyranuronosyloxy]oleanolate (5) (oleanolic acid=3β-hydroxyolean-12-en-28-oic acid).
oleanolic acid, triterpenoid saponins, machaerinic acid, Achyranthes aspera
Publication DOI: 10.1002/(SICI)1522-2675(20000216)83:2<359::AID-HLCA359>3.0.CO;2-7Journal NLM ID: 2985094RPublisher: Verlag Helvetica Chimica Acta
Institutions: Institut für Pharmazeutische Chemie, Universität Graz, Graz, Austria, Ethiopian Health and Nutrition Research Institute, Addis Ababa, Ethiopia, Institut für Pharmakognosie, Universität Graz, Graz, Austria, Schering A.G. Berlin, Berlin, Germany
Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, TLC, HPLC, extraction, evaporation, centrifugation, HR-EI-MS
- Article ID: 12748
Tanaka O, Han E-C, Yamaguchi H, Matsuura H, Murakami T, Taniyama T, Yoshikawa M "Saponins of plants of Panax species collected in central Nepal, and their chemotaxonomical significance. III." -
Chemical and Pharmaceutical Bulletin 48(6) (2000) 889-892
Panax pseudo-ginseng subsp. pseudo-ginseng has a carrot like root with a small rhizome. It was shown that the saponin composition of roots and rhizomes of this subspecies collected in Tibet and China was extremely poor. From the roots and rhizomes collected in Central Nepal, (specimen-PNct), only a small amount of an oleanolic acid saponin, β-D-glucopyranosyl-oleanolate (2) was isolated together with a polyacetylene-alcohol, panaxynol (3). In another specimen (specimen-PNs), also collected in Central Nepal, two oleanolic acid saponins, stipleanoside R2 (4) and chikusetsusaponin IV (5) were detected. No dammarane saponin was identified in either specimen. P. pseudo-ginseng subsp. himalaicus (Subsp-H) has a big rhizome with a small round root. From rhizomes and roots of this subsp. collected in Central Nepal (specimen-HNct), a fairly large amount of dammarane saponins, ginsenosides-Rb1 (6), -Rd (7), -Re (9) and -Rg1 (10), gypenoside XVII (8), notoginsenoside-R1 (11), majonoside-R2 (12) and pseudo-ginsenoside-F11 (13) were isolated, while no oleanane saponin (oleanolic acid saponin) was identified in this subsp. Based on the present and previous studies, medicinal evaluation and chemogeographical correlation of Himalayan Panax spp. are discussed.
chemotaxonomy, ginsenoside, araliaceae, saponin, Panax pseudo-ginseng, Himalayan Panax
NCBI PubMed ID: 10866157Publication DOI: 10.1248/cpb.48.889Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Correspondence: Tanaka O
Institutions: Kyoto Pharmaceutical University, Kyoto, Japan, Institute of Pharmaceutical Sciences, Faculty of Medicine, Hiroshima University, Hiroshima, Japan, Korea Wild Ginseng Research Insitute, Gangnung City, South Korea, Health Care Institute of Wakunaga Pharmaceutical Co. Ltd., Hiroshima, Japan
- Article ID: 12875
Yoshikawa M, Matsuda H "Antidiabetogenic activity of oleanolic acid glycosides from medicinal foodstuffs" -
BioFactors 13(1-4) (2000) 231-237
Oleanolic acid glycosides from several medicinal foodstuffs were found to show potent inhibitory activity on the increase of serum glucose levels in oral glucose-loaded rats. By examination of the structure-activity relationships, the 3-O-glucuronide moiety and the 28-carboxyl group in oleanolic acid glycosides were required to exert the hypoglycemic activity. Oleanolic acid glycosides were found to have neither insulin-like nor insulin-releasing activity, but they inhibited gastric emptying and glucose-uptake in the small intestine. Investigation of the mode of action revealed that the inhibition of gastric emptying was mediated by capsaicin-sensitive sensory nerves and the central nervous system. Furthermore, oleanolic acid glycosides were suggested to suppress the gastric emptying by stimulating the release and/or production of dopamine to act through dopamine2 receptors, which in turn causes the release of prostaglandins.
hypoglycemic activity, oleanolic acid glycosides, inhibitory activity, serum glucose
NCBI PubMed ID: 11237187Publication DOI: 10.1002/biof.5520130136Journal NLM ID: 8807441Publisher: Oxford; Washington, DC: IRL Press, International Union of Biochemistry
Correspondence: Yoshikawa M
Institutions: Kyoto Pharmaceutical University, Kyoto, Japan
Methods: biological assays
- Article ID: 12910
Melek FR, Miyase T, el-Gindy MR, Abdel-Khalik SM, Ghaly NS, el-Kady M "Saponins from Fagonia glutinosa" -
Die Pharmazie 55(10) (2000) 772-776
Twelve triterpenoid saponins, including six new, were isolated and identified from the aerial parts of Fagonia glutinosa. The new saponins were characterised as 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D-glucopyranosyl(1-->3)]-alpha-L - arabinopyranosyl-27-hydroxy oleanolic acid 28-O-beta-D-glucopyranosyl ester, 3-O-[beta-D-glucopyranosyl(1-->3)]-alpha-L-arabinopyranosyl ursolic acid, 3-O-alpha-L-arabinopyranosyl ursolic acid 28-O-beta-D-glucopyranosyl ester, 3-O-[beta-D-xylopyranosyl(1-->2)][beta- D-glucopyranosyl(1-->3)]-alpha-L-arabinopyranosyl ursolic acid, 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D- glucopyranosyl(1-->3)]-alpha-L-arabinopyranosyl ursolic acid 28-O-beta-D-glucopyranosyl ester and 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D-glucopyranosyl(1-->3)]-alpha-L - arabinopyranosyl-27-hydroxy ursolic acid 28-O-beta-D-glucopyranosyl ester. The structures of the saponins were established by spectral and chemical evidences. The assignments of the NMR signals were performed by means of HOHAHA, 1H-1H COSY, ROE, HMQC and HMBC experiments.
NCBI PubMed ID: 11082842Journal NLM ID: 9800766Publisher: Eschborn: Govi-Verlag Pharmazautischer Verlag
Institutions: Chemistry of Natural Products Department, University of Shizuoka, Japan
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
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10. Compound ID: 31987
Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136044,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_190606,IEDB_423153,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 12326
Kunert O, Haslinger E, Schmid MG, Reiner J, Bucar F, Mulatu E, Abebe D, Debella A "Three saponins, a steroid, and a flavanol glycoside from Achyrantes aspera" -
Monatshefte für Chemie 131(2) (2000) 195-204
Three bisdesmosidic saponins, 20-hydroxyecdysone, and quercetin-3-O-β-D-galactoside were isolated from the methanol extract of the aerial parts of Achyranthes aspera L. (Amaranthaceae). Their structures were established on the basis of NMR spectroscopic analysis; the complete 1H and 13C assignments of the compounds were achieved by means of 2D NMR studies.
NMR spectroscopy, structure elucidation, natural products, saponins
Publication DOI: 10.1007/PL00010306Journal NLM ID: 0254164Publisher: Wien, New York: Springer-Verlag
Institutions: Institut für Pharmazeutische Chemie, Universität Graz, Graz, Austria, Ethiopian Health and Nutrition Research Institute, Addis Ababa, Ethiopia, Institut für Pharmakognosie, Universität Graz, Graz, Austria, Laboratory for Organic Chemistry I, University of Bayreuth, Bayreuth, Germany
- Article ID: 12480
Michl G, Abebe D, Bucar F, Debella A, Kunert O, Schmid MG, Mulatu E, Haslinger E "New triterpenoid saponins from Achyrantes aspera Linn." -
Helvetica Chimica Acta 83(2) (2000) 359-363
Two new bisdesmosidic triterpenoid saponins, i.e. 1 and 2, were isolated, besides the three known saponins 3–5, from the MeOH extract of the aerial parts of Achyranthes aspera Linn. (Amaranthaceae). Their structures were elucidated as β-D-glucopyranosyl 3β-[O-α-L-rhamnopyranosyl-(1→3)-O-β-D-glucopyranuronosyloxy]machaerinate (1) and β-D-glucopyranosyl 3β-[O-β-D-galactopyranosyl-(1→2)-O-α-D-glucopyranuronosyloxy]machaerinate (2) by NMR spectroscopy, including 2D-NMR experiments (machaerinic acid=3β,21β-dihydroxyolean-12-en-28-oic acid). The other saponins were identified as β-D-glucopyranosyl 3β[O-α-L-rhamnopyranosyl-(1→3)-O-β-D-glucopyranuronosyloxy]oleanolate (3), β-D-glucopyranosyl 3-β-[O-β-D-galactopyranosyl-(1→2)-O-β-D-glucopyranuronosyloxy]oleanolate (4), and β-D-glucopyranosyl 3β-[O-β-D-glucopyranuronosyloxy]oleanolate (5) (oleanolic acid=3β-hydroxyolean-12-en-28-oic acid).
oleanolic acid, triterpenoid saponins, machaerinic acid, Achyranthes aspera
Publication DOI: 10.1002/(SICI)1522-2675(20000216)83:2<359::AID-HLCA359>3.0.CO;2-7Journal NLM ID: 2985094RPublisher: Verlag Helvetica Chimica Acta
Institutions: Institut für Pharmazeutische Chemie, Universität Graz, Graz, Austria, Ethiopian Health and Nutrition Research Institute, Addis Ababa, Ethiopia, Institut für Pharmakognosie, Universität Graz, Graz, Austria, Schering A.G. Berlin, Berlin, Germany
Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, TLC, HPLC, extraction, evaporation, centrifugation, HR-EI-MS
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11. Compound ID: 32380
|
b-D-Glcp-(1-28)-+
|
a-L-Rhap-(1-3)-b-D-GlcpA-(1-3)-Subst
Subst = machaerinic acid = SMILES O{3}[C@H]1CC[C@@]2([C@]3(CC=C4[C@@]5(CC({21}[C@@H](O)C[C@@]5(CC[C@]4([C@@]3(CC[C@@]2([H])C1(C)C)C)C){28}C(O)=O)(C)C)[H])[H])C |
Show graphically |
Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136105,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 12480
Michl G, Abebe D, Bucar F, Debella A, Kunert O, Schmid MG, Mulatu E, Haslinger E "New triterpenoid saponins from Achyrantes aspera Linn." -
Helvetica Chimica Acta 83(2) (2000) 359-363
Two new bisdesmosidic triterpenoid saponins, i.e. 1 and 2, were isolated, besides the three known saponins 3–5, from the MeOH extract of the aerial parts of Achyranthes aspera Linn. (Amaranthaceae). Their structures were elucidated as β-D-glucopyranosyl 3β-[O-α-L-rhamnopyranosyl-(1→3)-O-β-D-glucopyranuronosyloxy]machaerinate (1) and β-D-glucopyranosyl 3β-[O-β-D-galactopyranosyl-(1→2)-O-α-D-glucopyranuronosyloxy]machaerinate (2) by NMR spectroscopy, including 2D-NMR experiments (machaerinic acid=3β,21β-dihydroxyolean-12-en-28-oic acid). The other saponins were identified as β-D-glucopyranosyl 3β[O-α-L-rhamnopyranosyl-(1→3)-O-β-D-glucopyranuronosyloxy]oleanolate (3), β-D-glucopyranosyl 3-β-[O-β-D-galactopyranosyl-(1→2)-O-β-D-glucopyranuronosyloxy]oleanolate (4), and β-D-glucopyranosyl 3β-[O-β-D-glucopyranuronosyloxy]oleanolate (5) (oleanolic acid=3β-hydroxyolean-12-en-28-oic acid).
oleanolic acid, triterpenoid saponins, machaerinic acid, Achyranthes aspera
Publication DOI: 10.1002/(SICI)1522-2675(20000216)83:2<359::AID-HLCA359>3.0.CO;2-7Journal NLM ID: 2985094RPublisher: Verlag Helvetica Chimica Acta
Institutions: Institut für Pharmazeutische Chemie, Universität Graz, Graz, Austria, Ethiopian Health and Nutrition Research Institute, Addis Ababa, Ethiopia, Institut für Pharmakognosie, Universität Graz, Graz, Austria, Schering A.G. Berlin, Berlin, Germany
Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, TLC, HPLC, extraction, evaporation, centrifugation, HR-EI-MS
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12. Compound ID: 32381
|
b-D-Glcp-(1-28)-+
|
b-D-Galp-(1-3)-b-D-GlcpA-(1-3)-Subst
Subst = machaerinic acid = SMILES O{3}[C@H]1CC[C@@]2([C@]3(CC=C4[C@@]5(CC({21}[C@@H](O)C[C@@]5(CC[C@]4([C@@]3(CC[C@@]2([H])C1(C)C)C)C){28}C(O)=O)(C)C)[H])[H])C |
Show graphically |
Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136044,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_190606,IEDB_423153,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 12480
Michl G, Abebe D, Bucar F, Debella A, Kunert O, Schmid MG, Mulatu E, Haslinger E "New triterpenoid saponins from Achyrantes aspera Linn." -
Helvetica Chimica Acta 83(2) (2000) 359-363
Two new bisdesmosidic triterpenoid saponins, i.e. 1 and 2, were isolated, besides the three known saponins 3–5, from the MeOH extract of the aerial parts of Achyranthes aspera Linn. (Amaranthaceae). Their structures were elucidated as β-D-glucopyranosyl 3β-[O-α-L-rhamnopyranosyl-(1→3)-O-β-D-glucopyranuronosyloxy]machaerinate (1) and β-D-glucopyranosyl 3β-[O-β-D-galactopyranosyl-(1→2)-O-α-D-glucopyranuronosyloxy]machaerinate (2) by NMR spectroscopy, including 2D-NMR experiments (machaerinic acid=3β,21β-dihydroxyolean-12-en-28-oic acid). The other saponins were identified as β-D-glucopyranosyl 3β[O-α-L-rhamnopyranosyl-(1→3)-O-β-D-glucopyranuronosyloxy]oleanolate (3), β-D-glucopyranosyl 3-β-[O-β-D-galactopyranosyl-(1→2)-O-β-D-glucopyranuronosyloxy]oleanolate (4), and β-D-glucopyranosyl 3β-[O-β-D-glucopyranuronosyloxy]oleanolate (5) (oleanolic acid=3β-hydroxyolean-12-en-28-oic acid).
oleanolic acid, triterpenoid saponins, machaerinic acid, Achyranthes aspera
Publication DOI: 10.1002/(SICI)1522-2675(20000216)83:2<359::AID-HLCA359>3.0.CO;2-7Journal NLM ID: 2985094RPublisher: Verlag Helvetica Chimica Acta
Institutions: Institut für Pharmazeutische Chemie, Universität Graz, Graz, Austria, Ethiopian Health and Nutrition Research Institute, Addis Ababa, Ethiopia, Institut für Pharmakognosie, Universität Graz, Graz, Austria, Schering A.G. Berlin, Berlin, Germany
Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, TLC, HPLC, extraction, evaporation, centrifugation, HR-EI-MS
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