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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

• 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/s11694-019-00099-3
  Publisher: 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
  
   
  
  Morchella esculenta
  CSDB ID 49696 (all data & tools)
• 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/np50071a030
  Journal NLM ID: 7906882
  Publisher: 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
  
   
  
  Epimedium pubescens
  CSDB ID 51100 (all data & tools)
• 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-K
  Journal NLM ID: 0151434
  Publisher: 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
  
   
  
  Epimedium koreanum
  CSDB ID 50520 (all data & tools)
• 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/jf00035a025
  Journal NLM ID: 0374755
  Publisher: American Chemical Society
  Institutions: Department of Food Science and Technology, Wiegand Hall, Oregon State University, Corvallis, Oregon, USA
  Methods: HPLC
  
   
  
  Rubus idaeus
  CSDB ID 131305 (all data & tools)
• 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)83076-9
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Departamento de Químíca Orgánica, Facultad Químicas, Burjasot, Valencia, Spain
  Methods: 13C NMR, 1H NMR, UV, CC, FD-MS, PC
  
   
  
  Anthyllis onobrychioides
  CSDB ID 145457 (all data & tools)
• 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-V
  Journal NLM ID: 0151434
  Publisher: 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
  
   
  
  Epimedium wushanense
  CSDB ID 295636 (all data & tools)
• 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)00905-9
  Journal NLM ID: 0151434
  Publisher: 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
  
   
  
  Rhododendron ellipticum
  CSDB ID 146800 (all data & tools)
• 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-V
  Journal NLM ID: 0151434
  Publisher: 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
  
   
  
  Zanthoxylum bungeanum
  CSDB ID 146805 (all data & tools)
• 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: 9214739
  Publication DOI: 10.1021/np970025k
  Journal NLM ID: 7906882
  Publisher: 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
  
   
  
  Microtea debilis
  CSDB ID 60257 (all data & tools)
• 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)00017-4
  Journal NLM ID: 0151434
  Publisher: 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
  
   
  
  Acanthopanax divaricatus
  CSDB ID 60260 (all data & tools)
• 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)00842-4
  Journal NLM ID: 0151434
  Publisher: 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
  
   
  
  Byrsonima crassifolia
  CSDB ID 60274 (all data & tools)
• 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)00706-6
  Journal NLM ID: 0151434
  Publisher: 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
  
   
  
  Embelia schimperi
  CSDB ID 60395 (all data & tools)
• 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: 21710340R
  WWW link: http://www.yxxb.com.cn:8081/aps/CN/abstract/abstract9158.shtml
  Publisher: 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
  
   
  
  Prunella vulgaris
  CSDB ID 62393 (all data & tools)
• 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)00496-8
  Journal NLM ID: 0151434
  Publisher: 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
  
   
  
  Saxifraga stellaris
  CSDB ID 62995 (all data & tools)
• 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: 17260291
  Publication DOI: 10.1055/s-2006-960845
  Journal NLM ID: 0066751
  Publisher: 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
  
   
  
  Alchemilla speciosa
  CSDB ID 63007 (all data & tools)
• 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: 10479312
  Publication DOI: 10.1021/np9900674
  Journal NLM ID: 7906882
  Publisher: 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
  
   
  
  Polygonum salicifolium
  CSDB ID 63330 (all data & tools)
• 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)00116-2
  Journal NLM ID: 9884964
  Publisher: Amsterdam; New York: Elsevier
  Correspondence: a.de.jager@fpo.agro.nl
  Institutions: Fruit Research Station, Zetten, The Netherlands
  Methods: UV, extraction, RP-HPLC, spectrophotometry
  
   
  
  Malus domestica cv. Jonagold, Malus domestica cv. Elstar
  CSDB ID 64774 (all data & tools)
• 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)00124-7
  Journal NLM ID: 9882883
  Publisher: 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
  
   
  
  Malus domestica cv. Jonagold, Malus domestica cv. Elstar, Malus domestica cv. Elshof, Malus domestica cv. Red Elstar
  CSDB ID 64783 (all data & tools)
• 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: 21710340R
  Publisher: Beijing: Zhongguo yao xue hui
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, extraction, CC, melting point determination
  
   
  
  Geranium dahuricum
  CSDB ID 65120 (all data & tools)
• 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: 10995297
  Publication DOI: 10.1021/jf0002387
  Journal NLM ID: 0374755
  Publisher: 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
  
   
  
  Lactuca sativa
  CSDB ID 65375 (all data & tools)
• 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: 10746883
  Publication DOI: 10.1016/s0031-9422(99)00598-1
  Journal NLM ID: 0151434
  Publisher: 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
  
   
  
  Cotoneaster orbicularis
  CSDB ID 65397 (all data & tools)
• 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: 10939359
  Publication DOI: 10.1016/s0031-9422(00)00124-2
  Journal NLM ID: 0151434
  Publisher: 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
  
   
  
  Trifolium repens
  CSDB ID 65479 (all data & tools)
• 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: 10890521
  Publication DOI: 10.1016/s0021-9673(00)00059-5
  Journal NLM ID: 9318488
  Publisher: Amsterdam; New York: Elsevier
  Institutions: Research Laboratory of Natural Products Chemistry, A. M. Todd Botanicals, Eugene, USA
  
   
  
  Trifolium pratense, Citrus aurantium, Pueraria lobata, Astragalus, Aesculus hippocastanum, Panax ginseng
  CSDB ID 65725 (all data & tools)
• 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-G
  Journal NLM ID: 0376334
  Publisher: 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
  
   
  
  Malus domestica
  CSDB ID 65827 (all data & tools)
• 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: 10725600
  Publication DOI: 10.1016/s0305-1978(99)00084-8
  Journal NLM ID: 0430442
  Publisher: 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
  
   
  
  Fallopia
  CSDB ID 65976 (all data & tools)
• 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: 10901280
  Publication DOI: 10.1016/s0024-3205(00)00608-1
  Journal NLM ID: 0375521
  Publisher: 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
  
   
  
  Crataegus oxyacantha, Crataegus monogyna
  CSDB ID 65984 (all data & tools)
• 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/PL00010306
  Journal NLM ID: 0254164
  Publisher: 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
  
   
  
  Achyranthes aspera
  CSDB ID 66149 (all data & tools)
• 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:1005582611863
  Journal NLM ID: 7505563
  Publisher: Springer
  Correspondence: mllaitin@cc.joensuu.fi
  Institutions: Finnish Forest Research Institute, Punkaharju Research Station, Punkaharju, Finland, Department of Biology, University of Joensuu, Joensuu, Finland
  
   
  
  Betula pendula
  CSDB ID 66183 (all data & tools)
• 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: 10727823
  Publication DOI: 10.1016/s0367-326x(99)00147-1
  Journal NLM ID: 16930290R
  Publisher: 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
  
   
  
  Ipomoea fistulosa
  CSDB ID 66207 (all data & tools)
• 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: 10650086
  Publication DOI: 10.1021/np990391z
  Journal NLM ID: 7906882
  Publisher: 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
  
   
  
  Alangium chinense
  CSDB ID 66404 (all data & tools)
• 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)00060-5
  Journal NLM ID: 0430442
  Publisher: Pergamon Press
  Correspondence: Ivancheva S
  Institutions: Institute of Botany, Bulgarian Academy of Sciences, Sofia, Bulgaria
  Methods: TLC, extraction, CC, evaporation
  
   
  
  Geranium sylvaticum
  CSDB ID 66414 (all data & tools)
• 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: 11140534
  Publication DOI: 10.1016/s0031-9422(00)00216-8
  Journal NLM ID: 0151434
  Publisher: 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
  
   
  
  Asarum canadense
  CSDB ID 66423 (all data & tools)
• 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: 10691640
  Publication DOI: 10.1021/jf991002+
  Journal NLM ID: 0374755
  Publisher: 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
  
   
  
  Trifolium pratense
  CSDB ID 66556 (all data & tools)
• 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: 10949475
  Publication DOI: 10.1016/s0021-9673(00)00555-0
  Journal NLM ID: 9318488
  Publisher: 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
  
   
  
  Hypericum perforatum
  CSDB ID 66578 (all data & tools)
• 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: 11114003
  Publication DOI: 10.1002/1099-1573(200012)14:8<638::aid-ptr681>3.0.co;2-q
  Journal NLM ID: 8904486
  Publisher: Chichester: Wiley
  Institutions: Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Porto Alegre, Brazil
  Methods: biological assays
  
   
  
  Gochnatia polymorpha
  CSDB ID 66947 (all data & tools)
• 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/BF02492820
  Journal NLM ID: 0316520
  Publisher: Friedr. Vieweg Und Sohn Verlags Gmbh
  Institutions: Research Institute for Medicinal Plants, Budakalász, Hungary
  Methods: TLC, HPLC, extraction
  
   
  
  Hypericum perforatum
  CSDB ID 67189 (all data & tools)
• 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: 745047
  Publication DOI: 10.1248/yakushi1947.98.10_1395
  Journal NLM ID: 0413613
  Publisher: 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
  
   
  
  Apocynum venetum var. basikurumon
  CSDB ID 67571 (all data & tools)
• 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: 10793254
  Publication DOI: 10.1016/s0305-1978(99)00093-9
  Journal NLM ID: 0430442
  Publisher: 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
  
   
  
  Cercis chinensis, Cercis chinensis cv. 'Avondale', Cercis chingii, Cercis gigantea, Cercis occidentalis, Cercis reniformis
  CSDB ID 67636 (all data & tools)
• 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)00320-8
  Journal NLM ID: 9883240
  Publisher: 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
  
   
  
  (plant)
  CSDB ID 67949 (all data & tools)
• 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: 9714997
  WWW link: http://kpubs.org/article/articleMain.kpubs?articleANo=E1HSBY_2000_v6n2_82
  Publisher: 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
  
   
  
  Rosa arabica
  CSDB ID 67994 (all data & tools)
• 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: 10.1080/12538078.2000.10515843
  Journal NLM ID: 100955707
  Publisher: 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
  
   
  
  Argania spinosa
  CSDB ID 68087 (all data & tools)
• 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: 11199145
  Publication DOI: 10.1055/s-2000-9779
  Journal NLM ID: 0066751
  Publisher: 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
  
   
  
  Hypericum perforatum var. angustifolium
  CSDB ID 68169 (all data & tools)
• 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: 10763585
  Publication DOI: 10.1055/s-2000-11135
  Journal NLM ID: 0066751
  Publisher: 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
  
   
  
  Apocynum venetum
  CSDB ID 68652 (all data & tools)

Show legend Show as text

Structure type: monomer
C₂₁H₂₀O₁₁
Trivial name: quercitrin, baohuoside-II, quercetin 3-rhamnoside, quercetin 3-O-rhamnoside
Compound class: saponin glycoside, glycoside, flavonoid glycoside, flavonol glycoside
Contained glycoepitopes: IEDB_136105,IEDB_225177,IEDB_885823

• Article ID: 9204
  Liang HR, Vuorela P, Vuorela H, Hiltunen R "Isolation and immunomodulatory effect of flavonol glycosides from Epimedium hunanense" - Planta Medica 63(4) (1997) 316-319
  

  The ethyl acetate and n-butanol fractions from aerial parts of E. hunanense were initially screened to find active fractions with immunomodulatory activity. Nine compounds, tricin (1), luteolin (2), thalictoside (3), icariin I (4), baohuoside I (5), quercitrin (6), icariin (7), epimedin C (8), and B (9) were isolated from this species for the first time, and 3 was isolated for the first time from flavonoid extracts of the genus. Their structures were established by chemical and spectroscopic methods. The immunomodulatory effects of the n-butanol fraction and epimedin C isolated from the fraction were investigated. Hydrocortisone acetate (HCA) was used as an immunosuppressant to inhibit the immune response of mice. The n-butanol fraction and epimedin C significantly enhanced the response of spleen antibody-forming cells (SAFC) to near normal in the mice treated with HCA. They also significantly enhanced lymphocyte proliferation and caused a significant recovery of interleukin-2 (IL-2) production in the mice inhibited with HCA. In conclusion, they are active principles with immunoenhancing effects.

  flavonol glycosides, Epimedium hunanense, immunoenhancing effect, spleen antibody-forming cells (SAFC)

  NCBI PubMed ID: 9270375
  Publication DOI: 10.1055/s-2006-957690
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Institutions: Pharmacognosy Division, Department of Pharmacy, University of Helsinki, Helsinki, Finland
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, biological assays, radiolabeling, radioactivity measurement, HPLC, UV, extraction, CC, cytokine production, centrifugation, recrystallization
  
   
  
  Epimedium hunanense
  CSDB ID 50530 (all data & tools)
• Article ID: 10734
  Pietta P, Mauri P, Bruno A, Zini L "High-performance liquid chromatography and micellar electrokinetic chromatography of flavonol glycosides from Tilia" - Journal of Chromatography A 638 (1993) 357-361
  

  The determination of nine different flavonol glycosides from Tilia using reversed-phase high-performance liquid chromatography (HPLC) and micellar electrokinetic chromatography (MEKC) is described. The analytes were monitored by on-line diode-array UV detection to identify peaks as quercetin or kaempferol derivatives. MEKC is confirmed as a useful complementary technique to HPLC.

  Publication DOI: 10.1016/0021-9673(93)83449-3
  Journal NLM ID: 9318488
  Publisher: Amsterdam; New York: Elsevier
  Institutions: Università degli Studi di Milano, Milan, Italy, ITBA-CNR, Milan, Italy
  Methods: HPLC, UV, hydrolysis, MEKC
  
   
  
  Tilia cordata, Tilia platyphyllos
  CSDB ID 139118 (all data & tools)
• Article ID: 10744
  Ofman DJ, Markham KR, Vilain C, Molloy BPJ "Flavonoid profiles of New Zealand kauri and other species of Agathis" - Phytochemistry 38 (1995) 1223-1228
  

  This paper describes the flavonoid constituents in Agathis australis from a wide geographic range and completes a comprehensive survey of the flavonoid chemistry/chemotaxonomy of New Zealand conifers begun in 1984. Flavonol 3-O-glycosides and biflavones of the cupressuflavone and agathisflavone types are shown to be the predominant flavonoids. NMR data for these biflavones with varying degrees of methylation are presented for the first time. The flavonoid profiles of A. australis and three other species of Agathis show a high level of uniformity, and in this respect are closely related.

  chemotaxonomy, flavonoids, Agathis australis, Araucariaceae, biflavonoids, cupressuflavone, agathisflavone

  Publication DOI: 10.1016/0031-9422(94)00783-P
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: New Zealand Institute for Industrial Research and Development, Lower Hutt, New Zealand, Manaaki Whenua-Landcare Research, Lincoln, New Zealand
  Methods: 13C NMR, 1H NMR, TLC, LSI-MS, UV, 2D-PC
  
   
  
  Agathis atropurpurea, Agathis australis
  CSDB ID 146673 (all data & tools)
• 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-V
  Journal NLM ID: 0151434
  Publisher: 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
  
   
  
  Epimedium wushanense
  CSDB ID 245636 (all data & tools)
• 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)00905-9
  Journal NLM ID: 0151434
  Publisher: 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
  
   
  
  Rhododendron ellipticum
  CSDB ID 146798 (all data & tools)
• 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-V
  Journal NLM ID: 0151434
  Publisher: 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
  
   
  
  Zanthoxylum bungeanum
  CSDB ID 146807 (all data & tools)
• Article ID: 11090
  Zhong XN, Otsuka H, Ide T, Hirata E, Takushi A, Takeda Y "Three flavonol glycosides from leaves of Myrsine seguinii" - Phytochemistry 46(5) (1997) 943-946
  

  From the leaves of Myrsine seguinii, five flavonol glycosides were isolated. Two were identified as quercitrin and myricitrin, and the structures of the remaining three are quercetin 3-rhamnoside-3'-glucoside,myricetin 3-rhamnoside-3'-glucoside, and myricetin 3,4'-dirhamnoside.

  flavonol glycosides, quercitrin, myricitrin, Myrsine seguinii, Rapanea neriifolia, Myrsinaceae

  Publication DOI: 10.1016/S0031-9422(97)00366-X
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, l-2-3 Kasumi, Minami-ku, Hiroshtma 734, Japan
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, extraction
  
   
  
  Myrsine seguinii
  CSDB ID 60061 (all data & tools)
• 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: 9214739
  Publication DOI: 10.1021/np970025k
  Journal NLM ID: 7906882
  Publisher: 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
  
   
  
  Microtea debilis
  CSDB ID 60256 (all data & tools)
• 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)00017-4
  Journal NLM ID: 0151434
  Publisher: 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
  
   
  
  Acanthopanax divaricatus
  CSDB ID 60259 (all data & tools)
• 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)00706-6
  Journal NLM ID: 0151434
  Publisher: 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
  
   
  
  Embelia schimperi
  CSDB ID 60394 (all data & tools)
• Article ID: 11313
  de Almeida AP, Miranda MMFS, Simoni IC, Wigg MD, Lagrota MHC, Costa SS "Flavonol monoglycosides isolated from the antiviral fractions of Persea americana (Lauraceae) leaf infusion" - Phytotherapy Research 12(8) (1998) 562-567
  

  An infusion of Persea americana leaves (Lauraceae) strongly inhibited herpes simplex virus type 1 (HSV-1), Aujeszky's disease virus (ADV) and adeno virus type 3 (AD3) in cell cultures. Its fractionation, guided by anti-HSV-1 and ADV assays, allowed the isolation and identification of two new flavonol monoglycosides, kaempferol and quercetin 3-O-alpha-D-arabinopyranosides, along with the known kaempferol 3-O-alpha-L-rhamnopyranoside (afzelin), quercetin 3-O-alpha-L-rhamnopyranoside (quercitrin), quercetin 3-O-beta-glucopyranoside and quercetin, The known quercetin 3-O-beta-galactopyranoside was identified in a mixture. Afzelin and quercetin 3-O-alpha-D-arabinopyranoside showed higher activity against acyclovir-resistant HSV-I, Chlorogenic add significantly inhibited the HSV-1 replication without any cytotoxicity. However, all the substances tested were less active than the infusion or fractions. The same substances did not affect ADV replication. Chemical structures were elucidated by the analysis of UV, H-1 and C-13 NMR data, mainly by APT, homo and heteronuclear COSY experiments. The configuration of the D-arabinose unit, not usual in natural plant products, was established on the basis of the optical rotation of the free sugar obtained after acid hydrolysis.

  quercetin, leaves, quercitrin, Persea americana, kaempferol 3-o-alpha-d-arabinopyranoside, quercetin 3-o-alpha-d-arabinopyranoside, afzelin, quercetin 3-o-beta-glucopyranoside, quercetin 3-o-beta-galactopyranoside, chlorogenic acid, herpes simplex virus type 1, aujeszky's disease virus, adenovirus type 3

  Publication DOI: 10.1002/(SICI)1099-1573(199812)12:8<562::AID-PTR356>3.0.CO;2-6
  Journal NLM ID: 8904486
  Publisher: Chichester: Wiley
  Institutions: Núcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil, Instituto de Microbiologia, Departamento de Virologia, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil, Instituto Biológico de São Paulo, Seção de Biologia Celular, São Paulo, Brazil
  Methods: 13C NMR, 1H NMR, TLC, acid hydrolysis, paper chromatography, UV, optical rotation measurement, CC, melting point determination, antiviral assay
  
   
  
  Persea americana
  CSDB ID 61150 (all data & tools)
• Article ID: 11595
  Barakat HH "Chemical investigation of the constitutive phenolics of Ailanthus altissima; The structure of a new flavone glycoside gallate" - Natural Product Sciences 4(3) (1998) 153-157
  

  The aqueous ethanolic leaf extract of Ailanthus altissima was found to contain the new natural product, luteolin 7-O-β-(6'- galloylglucopyranoside), 13, along with fourteen known phenotic metabolites (1-12, 14 and 15). Structures of all compounds (1-15) were established by conventional methods of analysis and confirmed by FAB-MS, 1H- and 13C-NMR spectral analysis.

  13C-NMR, FAB-MS, phenolics, Simaroubaceae, Ailanthus altissima, luteolin 7-O-β-(6'- galloylglucopyranoside)

  Journal NLM ID: 9714997
  Publisher: Seoul, Korea: Korean Society of Pharmacognosy
  Institutions: National Research Centre, Dokki, Cairo, Egypt
  Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, UV, extraction, CC
  
   
  
  Ailanthus altissima
  CSDB ID 63741 (all data & tools)
• Article ID: 11700
  Cimanga K, De Bruyne T, Hu JP, Cos P, Apers S, Pieters L, Tona L, Van Den Berghe D, Vlietinck AJ "Constituents from Morinda morindoides leaves as inhibitors of xanthine oxidase and scavengers of superoxide anions" - Pharmacy and Pharmacology Communications 5(6) (1999) 419-424
  

  Morinda morindoides (Kongobololo or Nkongabululu) is one of the most popular medicinal plants used in the Democratic Republic of Congo. Ten of its constituent flavonoids were evaluated in the xanthine-xanthine oxidase enzymatic system. The compounds were identified by spectroscopic methods as quercetin (1), quercetin 7,4' dimethylether (2), luteolin 7 glucoside (3), apigenin 7 glucoside (4), quercetin 3 rhamnoside (5), kaempferol 3 rhamnoside (6), quercetin 3 rutinoside (7), kaempferol 3 rutinoside (8), chrysoeriol 7 neohesperidoside (9) and kaempferol 7 rhamnosylsophoroside (10). The aglycones chrysoeriol (11), kaempferol (12), luteolin (13) and apigenin (14), obtained by acid hydrolysis of the corresponding glycosides, were also included. Compound 5 exhibited only scavenging activity, 9 and 11 were devoid of any effect against xanthine oxidase and scavenging activity, and the remaining flavonoids exhibited xanthine oxidase inhibiting and superoxide scavenging activity to varying extent. Study of structure activity relationships demonstrated that the activity was not only dependent on the nature of substituents and the substitution site, but also on the nature of the aglycone. These results partially explain and support the use of Morinda morindoides in the treatment of rheumatism.

  flavonoid glycoside, Morinda morindoides, xanthine oxidase inhibition, superoxide anion scavanger

  Publication DOI: 10.1211/146080899128735009
  Journal NLM ID: 9807134
  Publisher: London: Pharmaceutical Press
  Institutions: Department of Pharmaceutical Sciences, University of Antwerp, Universiteitsplein 1, B 2610, Wilrijk, Antwerp, Belgium, Faculty of Pharmacy, University of Kinshasa, B.P. 212, Kinshasa XI, Congo
  Methods: statistical analysis, antioxidant activities
  
   
  
  Morinda morindoides
  CSDB ID 62554 (all data & tools)
• 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: 17260291
  Publication DOI: 10.1055/s-2006-960845
  Journal NLM ID: 0066751
  Publisher: 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
  
   
  
  Alchemilla speciosa
  CSDB ID 63008 (all data & tools)
• Article ID: 12005
  Ashida H, Fukuda I, Yamashita T, Kanazawa K "Flavones and flavonols at dietary levels inhibit a transformation of aryl hydrocarbon receptor induced by dioxin" - FEBS Letters 476(3) (2000) 213-217
  

  Dioxins invade the body mainly through the diet, and produce toxicity through the transformation of aryl hydrocarbon receptor (AhR). An inhibitor of the transformation should therefore protect against the toxicity and ideally be part of the diet. We examined flavonoids ubiquitously expressed in plant foods as one of the best candidates, and found that the subclasses flavones and flavonols suppressed antagonistically the transformation of AhR induced by 1 nM of 2,3,7,8-tetrachlorodibenzo-p-dioxin, without exhibiting agonistic effects that transform AhR. The antagonistic IC(50) values ranged from 0.14 to 10 μM, close to the physiological levels in human.

  flavonoid, cancer prevention, dioxin antagonist, aryl hydrocarbon receptor, transformation inhibitor, dietary phytochemical

  NCBI PubMed ID: 10913616
  Publication DOI: 10.1016/s0014-5793(00)01730-0
  Journal NLM ID: 0155157
  Publisher: Elsevier
  Correspondence: Kanazawa K
  Institutions: Laboratory of Food and Nutritional Chemistry, Faculty of Agriculture, Kobe University, Kobe, Japan
  Methods: DNA techniques, biological assays, radiolabeling, centrifugation, autoradiography
  
   
  
  (Streptophyta)
  CSDB ID 64752 (all data & tools)
• 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)00116-2
  Journal NLM ID: 9884964
  Publisher: Amsterdam; New York: Elsevier
  Correspondence: a.de.jager@fpo.agro.nl
  Institutions: Fruit Research Station, Zetten, The Netherlands
  Methods: UV, extraction, RP-HPLC, spectrophotometry
  
   
  
  Malus domestica cv. Jonagold, Malus domestica cv. Elstar
  CSDB ID 64775 (all data & tools)
• 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)00124-7
  Journal NLM ID: 9882883
  Publisher: 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
  
   
  
  Malus domestica cv. Jonagold, Malus domestica cv. Elstar, Malus domestica cv. Elshof, Malus domestica cv. Red Elstar
  CSDB ID 64784 (all data & tools)
• Article ID: 12064
  Chang Y-C, Chang F-R, Wu Y-C "The constituents of Lindera glauca" - Journal of the Chinese Chemical Society = Zhongguo hua hsueh hui hui zhi 47(2) (2000) 373-380
  

  Twenty-eight compounds including seven alkaloids, (+)-3-chloro-N-formylnornantenine (1), (+)-N-formylnornantenine (2), (+)-boldine (3), (+)-norboldine (4), (-)-norboldine (5), lycicamine (6), and tetrahydroberberine (7); four flavonoids, kaempferol (8), kaempferol-3-O-arabinoside (9), quercetin (10), and quercetin-3-O-rhamnoside (11); one butanolide, akolactone A (12); one p-quinone, 2,6-dimethoxy-p-quinone (13); one cyclohex-2-en-1-one, blumenol A (14); six benzenoids, methylparaben (15), p-hydroxybenzoic acid (16), vanillic acid (17), syringic acid (18), 3,4,5-trimethoxybenzoic acid (19), and 3-(3,4-dihydroxyphenyl) propionic acid (20); one diterpene, phytol (21); one triterpene, squalene (22); six steroids, (3-sitosterol (23), β-sitostenone (24), stigmasta-4,22-dien-3-one (25), 6β-hydroxy-β-sitostenone (26), 6β-hydroxystigmasterone (27), and β-sitosteryl-D-glucoside (28) were isolated from the aerial part of Lindera glauca. These compounds were characterized and identified by physical and spectral method. All compounds were isolated for the first time from this plant. Among them, (+)-3-chloro-N-formylnornantenine (1) is a new one.

  Lindera glauca

  Publication DOI: 10.1002/jccs.200000050
  Journal NLM ID: 16210600R
  Publisher: Taipei: Chinese Chemical Society
  Institutions: Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan, China, Department of Chemical Engineering, Kao Yuan Institute of Technology, Kaohsiung, Taiwan, China
  Methods: 13C NMR, 1H NMR, EI-MS, IR, UV, extraction, optical rotation measurement, CC, melting point determination, evaporation, PTLC
  
   
  
  Lindera glauca
  CSDB ID 65048 (all data & tools)
• 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: 10995297
  Publication DOI: 10.1021/jf0002387
  Journal NLM ID: 0374755
  Publisher: 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
  
   
  
  Lactuca sativa
  CSDB ID 65379 (all data & tools)
• 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-G
  Journal NLM ID: 0376334
  Publisher: 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
  
   
  
  Malus domestica
  CSDB ID 65829 (all data & tools)
• Article ID: 12246
  Hou AJ, Peng LY, Liu YZ, Lin ZW, Sun HD "Gallotannins and related polyphenols from Pistacia weinmannifolia" - Planta Medica 66(7) (2000) 624-626
  

  Two new gallotannins, pistafolins A (1) and B (2), were isolated from the leaf extract of Pistacia weinmannifolia. Their structures were determined by spectral methods. Four known gallotannins (3 - 6), seven known flavonoid glycosides (7 - 13), along with 1-O-β-D-(6′-O-galloyl)-glucopyranosyl-3-methoxy-5-hydroxybenzene (14), gallic acid (15), methyl gallate (16), (+)-catechin (17), and (+)-gallocatechin (18), were also isolated. Some of these compounds were tested for their cytotoxicity toward K562 cells, and two small molecular phenolic compounds, 15 and 18, showed significant inhibitory effects with IC50 values less than 5 μg/ml.

  cytotoxicity, B, polyphenols, Anacardiaceae, Pistacia weinmannifolia, gallotannin, pistafolins A

  NCBI PubMed ID: 11105566
  Publication DOI: 10.1055/s-2000-8633
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Correspondence: hdsun@mail.kib.ac.cn
  Institutions: Laboratory of Phytochemistry, Kunming Institute of Botany, Academia Sinica, Kunming, China, Department of Phytochemistry, Henan College of Traditional Chinese Medicine, Zhengzhou, China
  Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS, UV, extraction, optical rotation measurement, CC, cytotoxicity assay, evaporation, HR-FAB-MS
  
   
  
  Pistacia weinmannifolia
  CSDB ID 65854 (all data & tools)
• Article ID: 12263
  Kang TH, Jeong SJ, Kim NY, Higuchi R, Kim YC "Sedative activity of two flavonol glycosides isolated from the flowers of Albizzia julibrissin Durazz" - Journal of Ethnopharmacology 71(1-2) (2000) 321-323
  

  The flowers of Albizzia julibrissin are used as a sedative in oriental traditional medicine. The phytochemical study of this plant allowed the isolation of two flavonol glycosides, quercitrin (1) and isoquercitrin (2). The sedative activity of these compounds was evaluated, and both compounds 1 and 2 increased pentobarbital-induced sleeping time in dose-dependent manner in mice. These results support the use of the flowers of this plant as a sedative agent.

  flavonoids, Leguminosae, Albizzia julibrissin, sedative activity

  NCBI PubMed ID: 10904180
  Publication DOI: 10.1016/s0378-8741(99)00202-0
  Journal NLM ID: 7903310
  Publisher: Limerick: Elsevier Sequoia
  Correspondence: yckim@wonnms.wonkwang.ac.kr
  Institutions: Faculty of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan, College of Pharmacy, Wonkwang University, Iksan, South Korea
  Methods: 13C NMR, 1H NMR, biological assays, UV, extraction, CC, melting point determination
  
   
  
  Albizia julibrissin
  CSDB ID 65927 (all data & tools)
• Article ID: 12269
  Kawanishi K, Farnsworth NR "Current status of the chemistry and synthesis of natural antimalarial compounds and natural substances used to alleviate symptoms of diabetes (aldose reductase and α-glucosidase inhibitors)" - Book: Studies in Natural Products Chemistry (series: Bioactive Natural Products) (2000) Vol. 22, Chapter C, 145-192
  

  Atropine, camptothecin, cocaine, digitoxin, digoxin, morphine, pilocarpine, quinine, taxol, vinblastine and vincristine, among others, are important drugs obtained from higher plants and are used clinically. They have also served as lead compounds for the synthesis and modification of more effective and safer drugs, in many cases. In this chapter, drugs used as antimalarial compounds and for the complications of diabetes (aldose reductase and α-glucosidase inhibitors) will be discussed. Natural product chemists have isolated as little as 1.0 mg of pure compounds from natural sources and have been able to determine their structures using high resolution instrumental techniques. Organic chemists have synthesized thousands of compounds to produce one new drug on the basis of natural product leads, and pharmacologists and biochemists have tested their biological activity. Recently chemists and pharmacologists have worked together to develop techniques for studying structure-activity relationships using computer graphics and have designed new drugs. Biochemists, molecular biologists and pharmacologists have identified many receptors on which drugs act. Thus, mechanisms of drug action at the molecular level are being identified. From the accumulation of these results structure-activity relationships will lead to the preparation of thousands of useful compounds. We must produce drugs in these ways, because we cannot rely on solely on the limited amount of active compounds produced naturally in plants, in many cases, for a number of reasons. However we need to employ plant extracts themselves, because there are millions of people who cannot buy expensive synthetic drugs in the world and these extracts are widely used by them.

  Publication DOI: 10.1016/S1572-5995(00)80025-3
  Publisher: New York: Elsevier
  Editors: Atta-ur-Rahman
  Institutions: Kobe Pharmaceutical University, Kobe, Japan, Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA
  
   
  
  (plant)
  CSDB ID 65942 (all data & tools)
• 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: 10725600
  Publication DOI: 10.1016/s0305-1978(99)00084-8
  Journal NLM ID: 0430442
  Publisher: 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
  
   
  
  Fallopia
  CSDB ID 65979 (all data & tools)
• Article ID: 12320
  Kruthiventi AK, Krishnaswamy NR "Constituents of the flowers of Persea gratissima" - Fitoterapia 71(1) (2000) 94-96
  

  The flowers of Persea gratissima yielded an acylated flavonol 3-O-trans-p-coumaroylkaempferol (1), in addition to quercetin 3-O-rhamnoside (2) and isorhamnetin 3-O-glucoside (3).

  flavonoids, Persea gratissima

  NCBI PubMed ID: 11449484
  Publication DOI: 10.1016/s0367-326x(99)00125-2
  Journal NLM ID: 16930290R
  Publisher: Elsevier
  Institutions: Department of Chemistry, Sri Satya Sai Institute of Higher Learning, Prashantinilayam, India
  
   
  
  Persea gratissima
  CSDB ID 66133 (all data & tools)
• 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:1005582611863
  Journal NLM ID: 7505563
  Publisher: Springer
  Correspondence: mllaitin@cc.joensuu.fi
  Institutions: Finnish Forest Research Institute, Punkaharju Research Station, Punkaharju, Finland, Department of Biology, University of Joensuu, Joensuu, Finland
  
   
  
  Betula pendula
  CSDB ID 66188 (all data & tools)
• Article ID: 12334
  Lamba SS, Buch KY, Lewis III H, Lamba J "Phytochemicals as potential hypoglycemic agents" - Book: Studies in Natural Products Chemistry (series: Bioactive Natural Products) (2000) Vol. 21, Chapter B, 457-496
  

  Diabetes mellitus is a chronic metabolic disorder characterized by a high blood glucose concentration (hyperglycemia) which is due to insulin deficiency and/or insulin resistance. Hyperglycemia occurs because the liver and skeletal muscle cannot store glycogen and the tissues are unable to take up and utilize glucose. Treatment of diabetes is afforded by the following: (i) diet and exercise, (ii) insulin replacement therapy and (iii) the use of oral hypoglycemic agents. In folklore, a variety of plant extracts have been used to treat diabetic patients for centuries. Folklore has given the field of medicine many useful drugs, such pharmacologic prototypes include Digitalis(digitoxin, digoxin), Atropa, Hyoscyamnsand Datura(atropine, scopolamine), Catharanthus(vincristine, vinblastine), Erythroxylon(cocaine), Claviceps(ergonovine, ergotamine), Papaver(morphine, codeine and papaverine), Pilocarpus(pilocarpine) Rauvolfia(reserpine, rescinnamine, deserpidine), and Cinchona(quinine, quinidine); and many others. Obviously evaluation of plants and their active constituents has proven a very useful way of obtaining several useful therapeutic agents. Hence, a logical review of plant constituents having hypoglycemic activity could provide useful clues for obtaining new hypoglycemic agents. Plant constituents reportedly possessing hypoglycemic activity can be classified as follows: 1. Alkaloids; 2. Flavonoids and related compounds; 3. Glycosides/Steroids/Terpenoids; 4. Polysaccharides/ Proteins; and 5. Miscellaneous compounds. Phytoconstituents based upon the above classification are discussed including selected names of plants which are listed alphabetically according to genus. Appropriate data on their pharmacological activity, mechanisms of action (where applicable), and other relevant properties are discussed.

  diabetes mellitus, hypoglycemic activity, natural drugs

  Publication DOI: 10.1016/S1572-5995(00)80012-5
  Publisher: New York: Elsevier
  Editors: Atta-ur-Rahman
  Institutions: Florida A & M University, College of Pharmacy and Pharmaceutical Sciences, Tallahassee, USA, Parke-Davis, Division of Warner-Lambert Company, Morris Plain, USA
  
   
  
  (plant)
  CSDB ID 66190 (all data & tools)
• 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)00060-5
  Journal NLM ID: 0430442
  Publisher: Pergamon Press
  Correspondence: Ivancheva S
  Institutions: Institute of Botany, Bulgarian Academy of Sciences, Sofia, Bulgaria
  Methods: TLC, extraction, CC, evaporation
  
   
  
  Geranium sylvaticum
  CSDB ID 66415 (all data & tools)
• Article ID: 12401
  Lin L-C, Kuo Y-C, Chou C-J "Anti-herpes simplex virus type-1 flavonoids and a new flavanone from the root of Limonium sinense" - Planta Medica 66(4) (2000) 333-336
  

  From the root of Limonium sinense (Girard) Ktze a new (2R,3S)-3,5,7,4′-tetrahydroxy-3′,5′-dimethoxyflavanone was isolated and named isodihydrosyringetin (3), together with nine other known compounds, (-)-epigallocatechin 3-O-gallate (1), samarangenin B (2), myricetin (4), myricetin 3-O-α-rhamnopyranoside (5), quercetin 3-O-α-rhamnopyranoside (6), (-)-epigallocatechin (7), gallic acid (8), N-trans-caffeoyltyramine (9), and N-trans-feruloyltyramine (10). All of them were examined for their inhibitory effects on herpes simplex virus type-1 (HSV-1) replication in Vero cells. Both compounds 1 and 2 exhibited potent inhibitory activities in HSV-1 replication. Comparison of the IC50 values indicated that compounds 1 and 2 had higher inhibitory activities than the positive control acyclovir (38.6 ± 2.6 vs. 55.4 ± 5.3 μM, P < 0.001; 11.4 ± 0.9 vs. 55.4 ± 5.3 μM, P < 0.0005). Cytotoxicity was unlikely involved because no cell deaths were observable in the Vero cells following 5 day treatments with compound 1 or 2.

  inhibition, Limonium sinense, Plumbaginaceae, isodihydrosyringetin, herpes simplex virus type-1

  NCBI PubMed ID: 10865449
  Publication DOI: 10.1055/s-2000-8540
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Correspondence: lclin@cma23.nricm.edu.tw
  Institutions: National Research Institute of Chinese Medicine, Taipei, Taiwan, China
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, acid hydrolysis, biological assays, HPLC, alkaline hydrolysis, extraction, CI-MS, HR-ESI-MS, cytotoxicity assay, evaporation, centrifugation
  
   
  
  Limonium sinense
  CSDB ID 66506 (all data & tools)
• Article ID: 12402
  Lin L-C, Chou C-J "Flavonoids and phenolics from Limonium sinense" - Planta Medica 66(4) (2000) 382-383
  

  From the aerial part of Limonium sinense (Girard) Ktze, a new flavonol glycoside, myricetin 3-O-(2″-O-p-hydroxybenzoyl)-α-rhamnopyranoside has been isolated together with known flavonols, flavonol glycosides, flavonol glycoside gallates, flavones, flavanones, flavan-3-ols and gallic acid. The structural determinations of these compounds were based on spectral analyses.

  structural determination, phenolics, flavonoid glycosides, Limonium sinense

  NCBI PubMed ID: 10865464
  Publication DOI: 10.1055/s-2000-8547
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Correspondence: lclin@cma23.nricm.edu.tw
  Institutions: National Research Institute of Chinese Medicine, Taipei, Taiwan, China
  Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, TLC, HPLC, extraction, evaporation, centrifugation, HR-EI-MS
  
   
  
  Limonium sinense
  CSDB ID 66515 (all data & tools)
• 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: 10949475
  Publication DOI: 10.1016/s0021-9673(00)00555-0
  Journal NLM ID: 9318488
  Publisher: 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
  
   
  
  Hypericum perforatum
  CSDB ID 66579 (all data & tools)
• Article ID: 12487
  Min BS, Nakamura N, Miyashiro H, Kim Y-H, Hattori M "Inhibition of human immunodeficiency virus type 1 reverse transcriptase and ribonuclease H activities by constituents of Juglans mandshurica" - Chemical and Pharmaceutical Bulletin 48(2) (2000) 194-200
  

  From the stem-bark of Juglans mandshurica, two new naphthalenyl glucopyranosides, 1, 4, 8-trihydroxy-nahthalene 1-O-[α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside] (1) and 1, 4, 8-trihydroxynaphthalene 1-O-β-D[6'-O-(3", 5"-dihydroxy-4"-methoxybenzoyl)]glucopyranoside (4), and two new α-tetralonyl glucopyranosides, 4α, 5, 8-trihydroxy-α-tetralone 5-O-β-D-[6'-O-(3", 5"-dihydroxy-4"-methoxybenzoyl)glucopyranoside (7) and 4α, 5, 8-trihydroxy-α-tetralone 5-O-β-D-[6'-O-(3", 4", 5"-trihydroxybenzoyl)glucopyranoside (8), were isolated together with three known naphthalenyl glucopyranosides (2, 3 and 5), one α-tetralonyl glucopyranoside (6), four flavonoids (9-12), and two gaalloyl glucopyranosides (13, 14).Amongst the isolated compounds, 1, 2, 6-trigalloylglucopyranose (13) and 1, 2, 3, 6-tertagalloylglucopyranose (14) exhibited the most potent inhibition of reverse transcriptase (RT) activity with IC50 values of 0.067 and 0.040 μM, respectively, while the latter compound also inhibited ribonuclease H (RNase H) activity with an IC50 of 39 μM, comparable in potency to illimaquinone used as a positive contorl. 1, 4, 8-Trihydroxy-naphthalene 1-O-β-D-glucopyranoside (2), 1, 4, 8-trihydroxynaphthalene 1-O-β-D-[6'-O-(4"-hydroxy-3", 5"-dimethoxybenzoyl)]glu-copyranoside (3) and 8 showed moderate inhibition against both enyzme activities, and inhibitory potency of 2 against RNase H activity (IC50=156 μM) was slightly greater than that against the RT activity (IC50=290 μM).The inhibitory potencies of 4α, 5, 8-trihydroxy-α-tetralone 5-O-β-D-[6'-O-4"-hydroxy-3", 5"-dimethoxybenzoyl)] glucopyranoside (6), 7 and 8 against RT activity increased accompanied by an increase in the number of free hydroxyls on the galloyl residues, as represented by the IC50 values of >500, 330 and 5.8 μM, respectively.

  reverse transcriptase, Juglans mandshurica, human immunodeficienc virus, naphthalenyl glucopyranoside, ribonuclease H, α-tetralonyl glucopyranoside

  NCBI PubMed ID: 10705503
  Publication DOI: 10.1248/cpb.48.194
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: College of Pharmacy, Chungnam National University, Taejeon, South Korea, Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, Toyama, Japan
  Methods: biological assays
  
   
  
  Juglans mandshurica
  CSDB ID 66894 (all data & tools)
• Article ID: 12501
  Morand C, Manach C, Crespy V, Rémésy C "Respective bioavailability of quercetin aglycone and its glycosides in a rat model" - BioFactors 12(1-4) (2000) 169-174
  

  A large number of flavonoids, mostly O-glycosides, are found in foods of plant origin. The bound sugar moiety is known to influence their bioavailability. We examined here the effect of the nature of the sugar on the absorption of the glycosides. Four groups of rats (n=6) received a meal containing 20 mg of quercetin equivalents supplied as aglycone, quercetin 3-glucoside, quercetin 3-rhamnoside or rutin. Plasma were hydrolysed by a βglucuronidase/sulfatase and analyzed by HPLC coupled to UV detection at 370 nm. Four hours after the beginning of the meal, the quercetin metabolites present in plasma were identical in all groups but their total concentrations were quite different. With pure quercetin the circulating levels were 11.7± 1.8 μM, but this level was three fold higher when quercetin was supplied as quercetin 3-glucoside (33.2± 3.5 μM). By contrast, the plasma concentrations of quercetin metabolites was quite low with the rutin meal (about 3 μM) and undetectable after the quercetin 3-rhamnoside meal. These data suggest that the 3-O-glucosylation improves the absorption of quercetin in the small intestine, whereas the binding of a rhamnose or of a glucose-rhamnose moiety to the aglycone markedly depressed its absorption. Additionnal experiments have shown that the higher plasma levels measured after the meal containing quercetin 3-glucoside compared to quercetin were maintained throughout a 24 hour period following the meal. In conclusion, the nature of the glycosylation markedly influences the efficiency of quercetin absorption in rats. Quercetin 3-glucose can be absorbed in the small intestine and is better absorbed than quercetin itself. By contrast, glycosides containing a rhamnose moiety could not be absorbed in the small intestine.

  quercetin, quercetin glycosides, intestinal absorption, plasma metabolites

  NCBI PubMed ID: 11216481
  Publication DOI: 10.1002/biof.5520120127
  Journal NLM ID: 8807441
  Publisher: Oxford; Washington, DC: IRL Press, International Union of Biochemistry
  Correspondence: cmorand@clermont.inra.fr
  Institutions: Unité des Maladies Métaboliques et des Micronutriments, INRA Theix, Ceyrat, France
  Methods: biological assays, HPLC
  
   
  
  (plant)
  CSDB ID 66945 (all data & tools)
• 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/BF02492820
  Journal NLM ID: 0316520
  Publisher: Friedr. Vieweg Und Sohn Verlags Gmbh
  Institutions: Research Institute for Medicinal Plants, Budakalász, Hungary
  Methods: TLC, HPLC, extraction
  
   
  
  Hypericum perforatum
  CSDB ID 67191 (all data & tools)
• Article ID: 12559
  Okada Y, Miyauchi N, Suzuki K, Kobayashi T, Tsutsui C, Mayuzumi K, Nishibe S, Okuyama T "Search for naturally occurring substances to prevent the complications of diabetes. II. Inhibitory effect of coumarin and flavonoid derivatives on bovine lens aldose reductase and rabbit platelet aggregation" - Chemical and Pharmaceutical Bulletin 43(8) (1995) 1385-1387
  

  An EtOAc extract of Artemisiae Capillari Spica inhibited both bovine lens aldose reductase (bovine-LAR) and rabbit platelet aggregation. Two simple coumarins, scoparone (1) and scopoletin (2), and three flavonoids, capillarisin (21), cirsimaritin (22) and rhamnocitrin (23), were isolated from this extract. Scoparone (1) and scopoletin (2) exhibit a potent inhibitory effect on rabbit platelet aggregation induced by four types of agent, ADP, PAF, sodium arachidonate and/or collagen. Capillarisin (21) exhibits a potent inhibitory effect on bovine-LAR. In addition, thirteen simple coumarins, five coumarin glycosides and two flavonoids were tested for their inhibitory effect against bovine-LAR and rabbit platelet aggregation.

  flavonoid, diabetic complication, platelet aggregation, coumarin, Artemisiae Capillari Spica, bovine lens aldose reductase

  NCBI PubMed ID: 7553983
  Publication DOI: 10.1248/cpb.43.1385
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Department of Pharmacognosy and Phytochemistry, Meiji College of Pharmacy Research Laboratories of Biological Science, Kodama Limited Department of Pharmacognosy, Faculty of Pharmaceutical Sciences, Health Science University of Hokkaido
  Methods: inhibition studies, biological assays, extraction
  
   
  
  Artemisia capillaris
  CSDB ID 67216 (all data & tools)
• Article ID: 12578
  Palomino O, Gómez-Serranillos MP, Slowing K, Carretero E, Villar A "Study of polyphenols in grape berries by reversed-phase high-performance liquid chromatography" - Journal of Chromatography A 870(1-2) (2000) 449-451
  

  Several polyphenols have been tested in grape berries from Spain. The flavonoid content is important because of the pharmacological properties of these compounds, whereas resveratrol has been proved to be an antifungal, antiinflammatory and an anticarcinogenic compound. A reversed-phase HPLC method has been developed and applied to determine resveratrol, quercetine, quercitrine and rutine content in several grape berries samples in a single analysis. Covering the grapes with a preservative paper yields a healthier product, but one which has a lower polyphenol content than unprotected grapes.

  fruits; food analysis; polyphenols; flavonoids

  NCBI PubMed ID: 10722101
  Publication DOI: 10.1016/s0021-9673(99)01225-x
  Journal NLM ID: 9318488
  Publisher: Amsterdam; New York: Elsevier
  Correspondence: Gómez-Serranillos MP
  Institutions: Department of Pharmacology, Faculty of Pharmacy, Universidad Complutense de Madrid, Madrid, Spain
  Methods: extraction, RP-HPLC
  
   
  
  Vitis vinifera
  CSDB ID 67291 (all data & tools)
• Article ID: 12579
  Panizzi L, Catalano S, Miarelli C, Cioni PL, Campeol E "In vitro antimicrobial activity of extracts and isolated constituents of Geum rivale" - Phytotherapy Research 14(7) (2000) 561-563
  

  The antimicrobial activity of extracts of Geum rivale (Rosaceae) and that of some isolated constituents, on bacteria and fungi, was evaluated. The activity was concentrated in the triterpenes fraction and, for gram+ and gram- bacteria, also in the flavonoids fraction.

  Geum rivale; Rosaceae; triterpenes; flavonoids; tannins; antimicrobial activity

  NCBI PubMed ID: 11054853
  Publication DOI: 10.1002/1099-1573(200011)14:7<561::aid-ptr651>3.0.co;2-h
  Journal NLM ID: 8904486
  Publisher: Chichester: Wiley
  Institutions: Dipartimento di Bioorganica e Biofarmacia, Università di Pisa, Pisa, Italy, Sezione di Biotossicologia, Dipartimento di Prevenzione A.U.S.L., Livorno, Italy
  Methods: biological assays
  
   
  
  Geum rivale
  CSDB ID 67293 (all data & tools)
• 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: 10793254
  Publication DOI: 10.1016/s0305-1978(99)00093-9
  Journal NLM ID: 0430442
  Publisher: 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
  
   
  
  Cercis canadensis, Cercis canadensis ssp. mexicana, Cercis chinensis cv. 'Avondale', Cercis chingii, Cercis gigantea, Cercis reniformis, Cercis siliquastrum
  CSDB ID 67634 (all data & tools)
• 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: 9714997
  WWW link: http://kpubs.org/article/articleMain.kpubs?articleANo=E1HSBY_2000_v6n2_82
  Publisher: 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
  
   
  
  Rosa arabica
  CSDB ID 67996 (all data & tools)
• Article ID: 12721
  Strick R, Strissel PL, Borgers S, Smith SL, Rowley JD "Dietary bioflavonoids induce cleavage in the MLL gene and may contribute to infant leukemia" - Proceedings of the National Academy of Sciences of the USA 97(9) (2000) 4790-4795
  

  Chromosomal translocations involving the MLL gene occur in about 80% of infant leukemia. In the search for possible agents inducing infant leukemia, we identified bioflavonoids, natural substances in food as well as in dietary supplements, that cause site-specific DNA cleavage in the MLL breakpoint cluster region (BCR) in vivo. The MLL BCR DNA cleavage was shown in primary progenitor hematopoietic cells from healthy newborns and adults as well as in cell lines; it colocalized with the MLL BCR cleavage site induced by chemotherapeutic agents, such as etoposide (VP16) and doxorubicin (Dox). Both in vivo and additional in vitro experiments demonstrated topoisomerase II (topo II) as the target of bioflavonoids similar to VP16 and Dox. Based on 20 bioflavonoids tested, we identified a common structure essential for topo II-induced DNA cleavage. Reversibility experiments demonstrated a religation of the bioflavonoid as well as the VP16-induced MLL cleavage site. Our observations support a two-stage model of cellular processing of topo II inhibitors: The first and reversible stage of topo II-induced DNA cleavage results in DNA repair, but also rarely in chromosome translocations; whereas the second, nonreversible stage leads to cell death because of an accumulation of DNA damage. These results suggest that maternal ingestion of bioflavonoids may induce MLL breaks and potentially translocations in utero leading to infant and early childhood leukemia.

  doxorubicin, acute myelogenous leukemia, acute lymphoblastic leukemia, etoposide, topoisomerase II

  NCBI PubMed ID: 10758153
  Publication DOI: 10.1073/pnas.070061297
  Journal NLM ID: 7505876
  Publisher: National Academy of Sciences
  Correspondence: Strick R ; Strissel PL
  Institutions: University of Chicago, Department of Medicine, Section of Hematology/Oncology, Chicago, IL, USA
  Methods: biological assays
  
   
  
  (plant)
  CSDB ID 68029 (all data & tools)
• 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: 10.1080/12538078.2000.10515843
  Journal NLM ID: 100955707
  Publisher: 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
  
   
  
  Argania spinosa
  CSDB ID 68085 (all data & tools)
• 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: 11199145
  Publication DOI: 10.1055/s-2000-9779
  Journal NLM ID: 0066751
  Publisher: 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
  
   
  
  Hypericum perforatum var. angustifolium
  CSDB ID 68171 (all data & tools)
• Article ID: 12881
  Yu SJ, Abo-Elghar GE "Allelochemicals as inhibitors of glutathione S-transferases in the fall armyworm" - Pesticide Biochemistry and Physiology 68(3) (2000) 173-183
  

  Glutathione S-transferases (GSTs) isolated from larval midguts of the fall armyworm, Spodoptera frugiperda, were used to study their sensitivity to inhibition by 44 chemicals, most of which were plant allelochemi cals. Many flavonoids, other phenols, and α,β-unsaturated carbonyl compounds were potent inhibitors of the enzymes. For the flavonoids, apigenin was the best inhibitor among those studied, showing an I50 value of 0.82 μM. In general, flavonols exhibited higher inhibitory potencies than flavones; flavonoid glycosides were less inhibitory than their corresponding aglycones. In the case of phenols, tannic acid was the best inhibitor among those tested, showing an I50 value of 0.2 μM. The organotin compound chlorotriphenyltin was an potent as tannic acid in inhibiting the transferases. For the αβ-unsaturated carbonyl compounds, ethacrynic acid was the most potent inhibitor among those examined, showing an I50 value of 0.15 μM. However, the isothiocyanates were found to be marginal inhibitors of GSTs. GSTs isolated from larval fat bodies showed differential sensitivity to inhibition by some selected inhibitors compared with midgut GSTs. Kinetic studies of midgut GSTs revealed that ellagic acid exhibited a noncompetitive inhibition toward 1-chloro-2, 4-dinitrobenzene (CDNB) but a competitive inhibition toward glutathione (GSH). In contrast, inhibition by tannic acid and ethacrynic acid were noncompetitive toward both CDNB and GSH. Diethyl maleate did not affect GSH levels in midguts when larvae were topically treated with this compound for up to 24 h.

  inhibition, flavonoids, glutathione S-transferase, Spodoptera frugiperda

  Publication DOI: 10.1006/pest.2000.2514
  Journal NLM ID: 1301573
  Publisher: New York: Academic Press
  Institutions: Department of Entomology and Nematology, University of Florida, Gainesville, USA
  Methods: biological assays
  
   
  
  (plant)
  CSDB ID 68847 (all data & tools)
• Article ID: 12885
  Yuldashev MP, Batirov EK "A novel isoflavone glycoside from Caragana alaica" - Russian Journal of Bioorganic Chemistry 26(11) (2000) 787-789
  

  3-O-Rhamnopyranosylisorhamnetin, 3-O-glucopyranosylisorhamnetin, 7-O-galactopyranosylluteolin, quercitrin, isoquercitrin, wistin, and a novel isoflavonoid, 3′-hydroxy-6,4′-dimethoxy-7-O-β-D-glucopyranosylisoflavone, were isolated from the aerial parts of Caragana alaica. Of these, the previously described compounds were identified on the basis of their physicochemical and spectral characteristics, whereas the spectral analysis and conversion to a known compound, cladrastin, allowed the structural elucidation of the novel isoflavone glycoside.

  Caragana alaica, 3′-hydroxy-6, 4′-dimethoxy-7-O-β-D-glucopyranosylisoflavone, 3-O-rhamnopyranosylisorhamnetin, 3-O-glucopyranosylisorhamnetin, 7-O-galactopyranosylluteolin

  NCBI PubMed ID: 11696899
  Publication DOI: 10.1007/BF02759633
  Journal NLM ID: 9420101
  Publisher: Springer Science and Business Media
  Institutions: Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Republic of Uzbekistan, Tashkent, Uzbekistan
  Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, enzymatic hydrolysis, acid hydrolysis, HPLC, UV, extraction, optical rotation measurement, melting point determination, HR-FAB-MS
  
   
  
  Caragana alaica
  CSDB ID 68864 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 955 [M-H]-
C₄₈H₇₆O₁₉
Trivial name: protochiisanoside
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_136105,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_241101,IEDB_885823,IEDB_983931,SB_192

• 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)00017-4
  Journal NLM ID: 0151434
  Publisher: 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
  
   
  
  Acanthopanax divaricatus
  CSDB ID 60261 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: protochiisanoside
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_136105,IEDB_141806,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_225177,IEDB_241101,IEDB_885823,IEDB_983931,SB_192

• 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)00017-4
  Journal NLM ID: 0151434
  Publisher: 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
  
   
  
  Acanthopanax divaricatus
  CSDB ID 60262 (all data & tools)
• Article ID: 11815
  Zhu M, Li RC "Receptor binding activities of Schefflera triterpenoids and oligosaccharides" - Planta Medica 65(2) (1999) 99-103
  

  Roots and leaves of Schefflera bodinieri were studied for their activity in the central nervous system (CNS) by bioassay-guided isolation in conjunction with receptor binding assays. As demonstrated in preliminary screening, ethanol extracts of leaves and roots of S. bodinieri showed strong binding affinity to a number of CNS receptors. Chemical investigation of this plant species was then conducted and fourteen plant ingredients were obtained. In this study, nine of these isolated compounds were tested by fifteen receptor binding assays for their CNS activities. Results showed that three compounds, namely bodinone, bodinone glycoside and D-sorbitol, were able to selectively bind to muscarine receptors, a trisaccharide bound to Ca2+ channel and 5HT-2 receptors, stigmasterol 3-O-glucoside bound to 5HT- 2 receptors, and bodirin A bound to dopamine-2 receptors with IC50 values at μM level. In the drug-interaction studies, bodinone, bodinone glycoside, bodirin A, bodinitin A and the trisaccharide were found to affect binding affinity of certain specific binding agents to the 5HT1C, 5HT2, opiate, β- adrenergic and histamine 1 receptors. These observations suggest interactions between the plant ingredients and receptors as well as synergistic effect of various compounds at receptor level.

  interaction, araliaceae, Schefflera bodinieri, plant ingredients, receptor binding assay

  NCBI PubMed ID: 10193197
  Publication DOI: 10.1055/s-1999-13967
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Correspondence: Zhu M
  Institutions: Department of Pharmacy, Faculty of Medicine, The Chinese University of Hong Kong, Shatin, N.T., Hong Kong, China
  Methods: NMR, HPLC, binding assays
  
   
  
  Schefflera bodinieri
  CSDB ID 63101 (all data & tools)