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1. Compound ID: 23165
Structure type: oligomer
Trivial name: glucoluteolin
Compound class: saponin glycoside, glycoside, flavonoid glycoside, flavone glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_613439,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9473
Hirai Y, Sanada S, Ida Y, Shoji J "Studies on the constituents of Palmae plants. I. The constituents of Trachycarpus fortunei (Hook.) H. Wendl. (1)" -
Chemical and Pharmaceutical Bulletin 32(1) (1984) 295-301
The constituents of the leaves, stems and underground parts of Trachycarpus fortunei (HOOK.) H. WENDL. (Palmae) have been investigated. Glucoluteolin (3), luteolin 7-O-rutinoside (=scolymoside, 4) and methyl proto-Pb (6) from the leaves, dioscin (1), Pb (2), methyl protodioscin (5) and methyl proto-Pb (6) from the stems, and dioscin (1) and methyl proto-Pb (6) from the underground parts were isolated and identified. This is the first report of the isolation of steroidal saponins from Palmae plants and these results are interesting from the standpoint of chemotaxonomy.
diosgenin, furostanol oligoside, steroidal saponin, Trachycarpus fortunei, Palmae, proto-diosgenin, flavone glycoside, luteolin, glucoluteolin, scolymoside
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003624618Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, Showa University, Tokyo, Japan
Methods: 13C NMR, 1H NMR, IR, TLC, acid hydrolysis, GLC, enzymatic digestion, melting point determination, acetylation analysis
- Article ID: 9734
Hirai Y, Sanada S, Ida Y, Shoji J "Studies on the constituents of Palmae plants. III. The constituents of Chamaerops humilis L. and Trachycarpus wagnerianus Becc." -
Chemical and Pharmaceutical Bulletin 34 (1986) 82-87
The constituents of the leaves, stems and underground parts of Chamaerops humilis L. and Trachycarpus wagnerianus BECC. (Palmae) have been investigated. We isolated and identified methyl proto-dioscin and methyl proto-Pb from the stems, dioscin, Pb, methyl proto-dioscin, methyl proto-Pb and methyl proto-rhapissaponin from the underground parts, and tricin 7-O-rutinoside and methyl proto-Pb from the leaves of C. humilis L. On the other hand, we isolated and identified methyl proto-dioscin and pseudoproto-dioscin from the stems, Pb, Tg, methyl proto-Pb and pseudoproto-Pb from the underground parts, and glucoluteolin, scolymoside, methyl proto-Pb and pseudoproto-Pb from the leaves of T. wagnerianus BECC. This is the first report of the isolation of tricin 7-O-β-rutinoside, Tg and pseudodiosgenin oligosides from Palmae plants, and also the first discovery of pseudosteroidal saponin from natural sources.
diosgenin, Palmae, flavone glycoside, luteolin, Chamaerops humilis, Trachycarpus wagnerianus, sterodial saponin, pseudoproto-diosgenin, pennogenin, tricin
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003625978Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, Showa University, Japan
Methods: gel filtration, 13C NMR, 1H NMR, IR, TLC, acid hydrolysis, GLC, optical rotation measurement, melting point determination
- Article ID: 9912
Idaka K, Hirai Y, Shoji J "Studies on the constituents of Palmae plants. V. Steroid saponins and flavonoids of leaves of Phoenix rupicola T. Anderson, P. loureirii Kunth, P. reclinata N. J. Jacquin, and Arecastrum romanzoffianum Beccari" -
Chemical and Pharmaceutical Bulletin 39 (1991) 1455-1461
Steroid sponins and flavonoids of leaves of Phoenix rupicola T. ANDERSON, P. loureirii KUNTH, P. reclinata N. J. JACQUIN, and Arecastrum romanzoffianum BECCARI have been investigated. Tricin 7-O, β-D-glucopyranoside (I), vitexin (II), methyl proto-Pb (VII), methyl proto-taccaoside (26- O, β-D-glucopyranosyl (25R)-22-O-methyl-furost-5-en-3β,26-diol 3-O-[α-L-rhamnopyranosyl-(1→2)][α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside, VI), and methyl proto-rupicolaside (26-O, β-D-glucopyranosyl (25R)-22-O-methy-furost-5-en-3β,26-diol 3-O-[β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)][α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside, VIII) from P. rupicola, II, glucoluteolin (III), orientin (IV), isoorientin (V), VII, VIII, and methyl proto-loureiroside (26-O-β-D-glucopyranosyl (25R)-22-O-methyl-furost-5-en-3β,26-diol 3-O-[β-D-glucopyranosyl-(1→5)-α-L-arabinofuranosyl-(1→4)][α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside, IX) from P.loureirii, VII, VIII and methyl proto-reclinatoside (26-O-β-D-glucopyranosyl (25R)-22-O-methyl-furost-5-en-3β,26-diol 3-O-[α-L-rhamnopyranosyl-(1→5)-α-L-arabinofuranosyl-(1→4)][α-L-rhamnopyranosyl(1→2)]-β-D-glucopyranoside, X) from P. reclinata, III and VII from A. romanzoffianum were isolated are identified. VI, VIII, IX and X were the first isolated and characterized from natural sources.
flavonoid, diosgenin, furostanol oligoside, Palmae, proto-diosgenin, Phoenix rupicola, Phoenix loureirii, Phoenix reclinata, Arecastrum romanzoffianum, steroid saponin
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003629361Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, Showa University, Japan
Methods: 13C NMR, 1H NMR, IR, partial acid hydrolysis, TLC, acid hydrolysis, methanolysis, HPLC, enzymatic digestion, methylation analysis
- Article ID: 11495
Cuendet M, Potterat O, Hostettmann K "Iridoid glucosides, phenylpropanoid derivatives and flavonoids from Bartsia alpina" -
Pharmaceutical Biology 37(4) (1999) 318-320
Three iridoid glucosides, two phenylpropanoid derivatives and one flavonoid have been isolated from the methanolic whole plant extract of Bartsia alpina L. (Scrophulariaceae). Their structures were established by spectrometric (UV, D/CI and FAB mass spectrometry, 1H and 13C NMR) and chemical methods. Some of these compounds have radical scavenging activity against DPPH or antioxidant activity against beta-carotene on TLC bioassay.
flavonoid, Antioxidant activity, radical scavenging activity, Scrophulariaceae, Iridoids, phenylpropanoid derivatives, Bartsia alpina
Publication DOI: 10.1076/phbi.37.4.318.5808Journal NLM ID: 9812552Publisher: Lisse, the Netherlands: Swets & Zeitlinger
Correspondence: Hostettmann K
Institutions: Institut de Pharmacognosie et Phytochimie, Université de Lausanne, BEP, CH-1015 Lausanne, Switzerland
Methods: 13C NMR, 1H NMR, TLC, UV, antioxidant activities, MPLC, HPLC-UV
- Article ID: 12348
Santos DYAC, Salatino MLF "Foliar flavonoids of Annonaceae from Brazil: taxonomic significance" -
Phytochemistry 55(6) (2000) 567-573
Foliar flavonoids of 31 species of the Annonaceae native to Brazil, amounting to 76 compounds, were isolated and identified. All phenols found were glycosides of either flavones (apigenin, scutellarein, hispidulin and luteolin) or flavonols (kaempferol, rhamnocitrin, 6-hydroxyrhamnocitrin, quercetin, isorhamnetin and rhamnetin), with the latter predominating. Some members of the tribe Bocageeae are distinctive for accumulating 6-oxygenated flavones and flavonols, in addition to 7-O-methylated flavonols, a feature possibly linked to the assumed advanced condition of the tribe within the family. Members of Duguetia stand out for the apparent absence of quercetin glycosides. Anaxagorea dolichocharpa seemingly lacks flavones and flavonols entirely. A UPGMA analysis based on the distribution of flavonoids does not group the analyzed species according to the available tribal division of the Annonaceae. However, several taxonomically meaningful groupings emerged through the multivariate analysis.
Annonaceae; flavonoids; flavones; flavonols; UPGMA; chemotaxonomy
NCBI PubMed ID: 11130666Publication DOI: 10.1016/s0031-9422(00)00227-2Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: dyacsan@ib.usp.br
Institutions: Institute of Biosciences, University of São Paulo, São Paulo, Brazil
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2. Compound ID: 23166
Structure type: oligomer
Trivial name: glucoluteolin, luteolin 7-O-rutinoside scolymoside, eriocitrin, luteolin 7-rutinoside, scolymoside
Compound class: saponin glycoside, glycoside, flavonoid glycoside, flavonol glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144144,IEDB_146664,IEDB_225177,IEDB_613439,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9473
Hirai Y, Sanada S, Ida Y, Shoji J "Studies on the constituents of Palmae plants. I. The constituents of Trachycarpus fortunei (Hook.) H. Wendl. (1)" -
Chemical and Pharmaceutical Bulletin 32(1) (1984) 295-301
The constituents of the leaves, stems and underground parts of Trachycarpus fortunei (HOOK.) H. WENDL. (Palmae) have been investigated. Glucoluteolin (3), luteolin 7-O-rutinoside (=scolymoside, 4) and methyl proto-Pb (6) from the leaves, dioscin (1), Pb (2), methyl protodioscin (5) and methyl proto-Pb (6) from the stems, and dioscin (1) and methyl proto-Pb (6) from the underground parts were isolated and identified. This is the first report of the isolation of steroidal saponins from Palmae plants and these results are interesting from the standpoint of chemotaxonomy.
diosgenin, furostanol oligoside, steroidal saponin, Trachycarpus fortunei, Palmae, proto-diosgenin, flavone glycoside, luteolin, glucoluteolin, scolymoside
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003624618Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, Showa University, Tokyo, Japan
Methods: 13C NMR, 1H NMR, IR, TLC, acid hydrolysis, GLC, enzymatic digestion, melting point determination, acetylation analysis
- Article ID: 9734
Hirai Y, Sanada S, Ida Y, Shoji J "Studies on the constituents of Palmae plants. III. The constituents of Chamaerops humilis L. and Trachycarpus wagnerianus Becc." -
Chemical and Pharmaceutical Bulletin 34 (1986) 82-87
The constituents of the leaves, stems and underground parts of Chamaerops humilis L. and Trachycarpus wagnerianus BECC. (Palmae) have been investigated. We isolated and identified methyl proto-dioscin and methyl proto-Pb from the stems, dioscin, Pb, methyl proto-dioscin, methyl proto-Pb and methyl proto-rhapissaponin from the underground parts, and tricin 7-O-rutinoside and methyl proto-Pb from the leaves of C. humilis L. On the other hand, we isolated and identified methyl proto-dioscin and pseudoproto-dioscin from the stems, Pb, Tg, methyl proto-Pb and pseudoproto-Pb from the underground parts, and glucoluteolin, scolymoside, methyl proto-Pb and pseudoproto-Pb from the leaves of T. wagnerianus BECC. This is the first report of the isolation of tricin 7-O-β-rutinoside, Tg and pseudodiosgenin oligosides from Palmae plants, and also the first discovery of pseudosteroidal saponin from natural sources.
diosgenin, Palmae, flavone glycoside, luteolin, Chamaerops humilis, Trachycarpus wagnerianus, sterodial saponin, pseudoproto-diosgenin, pennogenin, tricin
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003625978Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, Showa University, Japan
Methods: gel filtration, 13C NMR, 1H NMR, IR, TLC, acid hydrolysis, GLC, optical rotation measurement, melting point determination
- Article ID: 10480
Ooghe WC, Ooghe SJ, Detavernier CM, Huyghebaert A "Characterization of orange juice (Citrus sinensis) by flavanone glycosides" -
Journal of Agricultural and Food Chemistry 42 (1994) 2183-2190
A fast and simple method has been developed to detect orange juice (Citrus sinensis) falsifications on the basis of the flavanone glycoside pattern. After a short sample preparation procedure, gradient HPLC is used, followed by photodiode array detection. Separation is done by means of a 15 cm Waters Novapak RP 18 column and a mobile phase gradient, partly replacing an aqueous phosphate buffer solution by acetonitrile. Peak identification is based on relative retention times as well as on W-vis spectra. On the basis of a minimum hesperididnarirutin ratio of 3, some doubtful technological processes, as further extraction of oranges, may be traced out, as well as the addition of Citrus reticulata and some orange hybrids. Also, the addition to Citrus sinensis of small amounts of Citrus paradisi, Citrus aurantium, andlor Citrus bergamia may be detected by the presence of naringin or some other flavonoids not present in Citrus sinensis.
adulteration, orange juice, flavanone glycosides
Publication DOI: 10.1021/jf00046a020Journal NLM ID: 0374755Publisher: American Chemical Society
Institutions: University of Gent, Gent, Belgium
Methods: HPLC
- Article ID: 11473
Shalaby NMM, Maghraby AS, El-Hagrassy AM "Effect of Daucus carota var. boissieri extracts on immune response of Schistosoma mansoni infected mice" -
Folia Microbiologica 44(4) (1999) 441-448
Isolation and structure elucidation was carried out of flavonoid constituents found in fractionated extracts of the seeds and green leaves of Daucus carota L. var. boissieri (Apiaceae). The flavonoids are mainly apigenin, luteolin, their glycosidic precursors and 2,4,5-trimethoxybenzaldehyde. Fatty acids, hydrocarbons and sterols were identified by GLC. The effect of various carrot extracts on the immune responses of Schistosoma mansoni infected mice was studied. The rate of reduction in worm infestation in mice injected with some fractions indicated a strong protection. Some extracts induced humoral immune response through raising the IgG level at 2, 4 and 6 weeks post-infection as compared with infected control. The phenotypic analysis of the cellular immune response in spleen and mesenteric lymph nodes was accomplished by direct immunofluorescence. The data showed that some extracts stimulated the blastogenesis of CD4+-T splenocytes and mesenteric lymph node cells.
flavonol glycoside, luteolin, apigenin, mesenteric lymph node, praziquantel, worm burden
NCBI PubMed ID: 10983240Publication DOI: 10.1007/bf02903720Journal NLM ID: 0376757Publisher: New York: Springer
Institutions: Laboratory of Natural Products, National Research Centre, Dokki, Cairo, Egypt, Laboratory of Therapeutical Chemistry, National Research Centre, Dokki, Cairo, Egypt
Methods: 1H NMR, GLC, UV, PC
- Article ID: 11493
Felser C, Schimmer O "Flavonoid glycosides from Alchemilla speciosa" -
Planta Medica 65(7) (1999) 668-670
The new flavonol glycosides quercetin 3-O-β-(2-O-α-L-rhamnopyranosyl)-glucopyranoside uronic acid and kaempferol 3-O-β-(2-O-α-L-rhamnopyranosyl)-glucopyranoside uronic acid were isolated from the leaves of Alchemilla speciosa Buser together with 13 known flavonol and flavone glycosides and (+)-catechin. The structures were determined by spectroscopic methods.
flavonol glycosides, Alchemilla speciosa, spectroscopic methods
NCBI PubMed ID: 17260291Publication DOI: 10.1055/s-2006-960845Journal NLM ID: 0066751Publisher: George Thieme
Institutions: Institut für Botanik und Pharmazeutische Biologie, Lehrstuhl Pharmazeutische Biologie, Universität Erlangen-Nürnberg, Erlangen, Germany
Methods: 13C NMR, 1H NMR, methylation, TLC, HPLC, UV, acetylation, HCl hydrolysis
- Article ID: 11977
Kim NM, Kim J, Chung HY, Choi JS "Isolation of luteolin 7-O-rutinoside and esculetin with potential antioxidant activity from the aerial parts of Artemisia montana" -
Archives of Pharmacal Research 23(3) (2000) 237-239
The antioxidant activity of Artemisia montana was determined by measuring the radical scavenging effect on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and inhibitory activity against free radical generation of hepatocytes (AC2F). The methanol extract of A. montana showed strong radical scavenging activity at a concentration of 10.1 μg/ml, and thus fractionated by solvent extraction. Esculetin and luteolin 7-O-rutinoside (scolymoside) were isolated as the active principles from the EtOAc and Interphase fractions, respectively. The antioxidant activity of these compounds were comparable to that of L-ascorbic acid.
Antioxidant activity, Artemisia montana, esculetin, luteolin 7-O-rutinoside
NCBI PubMed ID: 10896054Publication DOI: 10.1007/BF02976451Journal NLM ID: 8000036Publisher: Pharmaceutical Society of Korea
Correspondence: choijs@pknu.ac.kr
Institutions: Faculty of Food Science and Biotechnology, Pukyong National University, Pusan, South Korea, Masan College, Masan, South Korea, College of Pharmacy, Pusan National University, Pusan, South Korea
Methods: 13C NMR, 1H NMR, extraction, EI-MS, column chromatography, melting point determination, antioxidant activities, evaporation
- Article ID: 12187
Miyake Y, Shimoi K, Kumazawa S, Yamamoto K, Kinae N, Osawa T "Identification and antioxidant activity of flavonoid metabolites in plasma and urine of eriocitrin-treated rats" -
Journal of Agricultural and Food Chemistry 48(8) (2000) 3217-3224
Eriocitrin, a flavonoid glycoside present in lemon fruit, is metabolized in vivo to a series of eriodictyol, methylated eriodictyol, 3,4-dihydroxyhydrocinnamic acid, and their conjugates. Plasma antioxidant activity increased following oral administration of aqueous eriocitrin solutions to rats. Eriocitrin metabolites were found in plasma and renal excreted urine through HPLC and LC-MS analyses. Eriocitrin was not detected in plasma and urine, but eriodictyol, homoeriodictyol, and hesperetin in their conjugated forms were detected in plasma of 4.0 h following administration of eriocitrin. In urine for 24 h, both nonconjugates and conjugates of these metabolites were detected. 3,4-Dihydroxyhydrocinnamic acid, which is metabolized from eriodictyol by intestinal bacteria, was detected in slight amounts with each form in 4.0-h plasma and 24-h urine. Eriocitrin was suggested to be metabolized by intestinal bacteria, and then eriodictyol and 3,4-dihydroxyhydrocinnamic of its metabolite were absorbed. Following administration of eriocitrin, plasma exhibited an elevated resistance effect to lipid peroxidation. Eriocitrin metabolites functioning as antioxidant agents are discussed.
flavonoids; eriocitrin; antioxidant; metabolism; rats
NCBI PubMed ID: 10956094Publication DOI: 10.1021/jf990994gJournal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: yoshiaki_miyake@mr.pokka.co.jp
Institutions: Fundamental Technical Laboratory of Pokka Corporation, Ltd., Shikatsu-cho, Japan, School of Food and Nutritional Sciences, University of Shizuoka, Shizuoka, Japan, Laboratory of Food Biodynamics, Nagoya University Graduate School of Bioagricultural Sciences, Nagoya, Japan
Methods: biological assays
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3. Compound ID: 25684
Structure type: oligomer
Compound class: C-glycoside
Contained glycoepitopes: IEDB_581506,IEDB_613439
The structure is contained in the following publication(s):
- Article ID: 10350
Webby RF, Markham KR "Isoswertiajaponin 2''-O-β-arabinopyranoside and other flavone-C-glycosides from the antarctic grass Deschampsia antarctica deschampsia antarctica" -
Phytochemistry 36 (1994) 1323-1326
The major falvonoid constituents of the Antarctic grass, Deschampsia antarctica, are shown to be the C-glycosylfavones, isoswertiajaponin (7-O-methylorientin) 2''-O-β-arabinopyranoside and orientin. These are accompanied by lower levels of orientin 2''-O-arabinopyranoside, isoswertisin (7-O-methylvitexin) 2''-O-β-arabinopyranoside, acylated derivatives, isoswertisin, isoswertiajaponin and tricin. A preliminary study suggests that the overall level of flavonoids in Deschampsia increases during the Antarctic mid-summer.
acylation, Gramineae, Deschampsia antarctica, flavone C-glycosides, isoswertiajaponin 2′'-O-β-arabinopyranoside, isoswertisin 2′'-O-β-arabinopyranoside, orientin 2′'-O-β-arabinopyranoside, light-induced variation
NCBI PubMed ID: 7765369Publication DOI: 10.1016/S0031-9422(00)89660-0Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Industrial Research Ltd., Lower Hutt, New Zealand
Methods: 13C NMR, 1H NMR, TLC, UV, PC, CC
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4. Compound ID: 25685
Structure type: monomer
Compound class: C-glycoside
Contained glycoepitopes: IEDB_581506,IEDB_613439
The structure is contained in the following publication(s):
- Article ID: 10350
Webby RF, Markham KR "Isoswertiajaponin 2''-O-β-arabinopyranoside and other flavone-C-glycosides from the antarctic grass Deschampsia antarctica deschampsia antarctica" -
Phytochemistry 36 (1994) 1323-1326
The major falvonoid constituents of the Antarctic grass, Deschampsia antarctica, are shown to be the C-glycosylfavones, isoswertiajaponin (7-O-methylorientin) 2''-O-β-arabinopyranoside and orientin. These are accompanied by lower levels of orientin 2''-O-arabinopyranoside, isoswertisin (7-O-methylvitexin) 2''-O-β-arabinopyranoside, acylated derivatives, isoswertisin, isoswertiajaponin and tricin. A preliminary study suggests that the overall level of flavonoids in Deschampsia increases during the Antarctic mid-summer.
acylation, Gramineae, Deschampsia antarctica, flavone C-glycosides, isoswertiajaponin 2′'-O-β-arabinopyranoside, isoswertisin 2′'-O-β-arabinopyranoside, orientin 2′'-O-β-arabinopyranoside, light-induced variation
NCBI PubMed ID: 7765369Publication DOI: 10.1016/S0031-9422(00)89660-0Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Industrial Research Ltd., Lower Hutt, New Zealand
Methods: 13C NMR, 1H NMR, TLC, UV, PC, CC
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5. Compound ID: 26213
Structure type: monomer
Trivial name: glucoluteolin, luteolin 7-glucoside
Compound class: saponin glycoside, glycoside, flavonoid glycoside, flavonol glycoside, flavone glycoside, flavone glucoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_613439,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10482
Igile GO, Oleszek W, Jurzysta M, Burda S, Fafunso M, Fasanmade AA "Flavonoids from Vernonia amygdalina and their antioxidant activities" -
Journal of Agricultural and Food Chemistry 42 (1994) 2445-2448
Journal NLM ID: 0374755Publisher: American Chemical Society
- Article ID: 10583
Hu CQ, Chen K, Shi Q, Kilkuskie RE, Cheng YC, Lee KH "Anti-aids agents, 10. Acacetin-7-O-β-D-galactopyranoside, an anti-HIV principle from Chrysanthemum morifolium and a structure-activity correlation with some related flavonoids" -
Journal of Natural Products 57 (1994) 42-51
An active anti-HIV principle, acacetin-7-O-β-D-galactopyranoside, has been isolated from Chrysanthemum morifolium. Seven additional flavonoids isolated from this plant, 13 known related flavonoids, and 14 synthetic flavonoids were also evaluated as inhibitors of HIV replication in H9 cells. A known flavone, chrysin, was found to be the most promising compound in this series. Flavonoids with hydroxy groups at C-5 and C-7 and with a C-2-C-3 double bond were more potent inhibitors of HIV growth. In general, the presence of substituents (hydroxyl and halogen) in the B-ring increased toxicity and/or decreased activity.
NCBI PubMed ID: 8158164Publication DOI: 10.1021/np50103a006Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Institutions: Natural Products Laboratory, School of Pharmacy, University of North Carolina, Chapel Hill 27599
- Article ID: 10657
Hatam NAR, Seifert K "Favonoids from Achillea micrantha" -
Planta Medica 60 (1994) 600
NCBI PubMed ID: 17236094Publication DOI: 10.1055/s-2006-959589Journal NLM ID: 0066751Publisher: George Thieme
Institutions: Department of Chemistry, College of Sciences, Saddam University for Engineering and Science, Jadiriyah, Baghdad, Iraq
- Article ID: 11394
Cimanga K, De Bruyne T, Hu JP, Cos P, Apers S, Pieters L, Tona L, Van Den Berghe D, Vlietinck AJ "Constituents from Morinda morindoides leaves as inhibitors of xanthine oxidase and scavengers of superoxide anions" -
Pharmacy and Pharmacology Communications 5(6) (1999) 419-424
Morinda morindoides (Kongobololo or Nkongabululu) is one of the most popular medicinal plants used in the Democratic Republic of Congo. Ten of its constituent flavonoids were evaluated in the xanthine-xanthine oxidase enzymatic system. The compounds were identified by spectroscopic methods as quercetin (1), quercetin 7,4' dimethylether (2), luteolin 7 glucoside (3), apigenin 7 glucoside (4), quercetin 3 rhamnoside (5), kaempferol 3 rhamnoside (6), quercetin 3 rutinoside (7), kaempferol 3 rutinoside (8), chrysoeriol 7 neohesperidoside (9) and kaempferol 7 rhamnosylsophoroside (10). The aglycones chrysoeriol (11), kaempferol (12), luteolin (13) and apigenin (14), obtained by acid hydrolysis of the corresponding glycosides, were also included. Compound 5 exhibited only scavenging activity, 9 and 11 were devoid of any effect against xanthine oxidase and scavenging activity, and the remaining flavonoids exhibited xanthine oxidase inhibiting and superoxide scavenging activity to varying extent. Study of structure activity relationships demonstrated that the activity was not only dependent on the nature of substituents and the substitution site, but also on the nature of the aglycone. These results partially explain and support the use of Morinda morindoides in the treatment of rheumatism.
flavonoid glycoside, Morinda morindoides, xanthine oxidase inhibition, superoxide anion scavanger
Publication DOI: 10.1211/146080899128735009Journal NLM ID: 9807134Publisher: London: Pharmaceutical Press
Institutions: Department of Pharmaceutical Sciences, University of Antwerp, Universiteitsplein 1, B 2610, Wilrijk, Antwerp, Belgium, Faculty of Pharmacy, University of Kinshasa, B.P. 212, Kinshasa XI, Congo
Methods: statistical analysis, antioxidant activities
- Article ID: 11466
Sharaf M, El-Ansari MA, Saleh NAM "Flavone glycosides from Mentha longifolia" -
Fitoterapia 70(5) (1999) 478-483
In addition to isoorientin, vicenin-2, hypolaetin, lucenin-1, luteolin 7-O-glucoside and 7-O-neohesperidoside, the aerial parts of Mentha longifolia yielded three new flavonoids, identified as tricetin 7-O-methylether 3'-O glucoside 5'-O-rhamnoside (1), tricetin 3'-O glucoside 5'-O-rhamnoside (2) and tricetin 3'-O-rhamnosyl-(1→4)-rhamnoside (3).
flavonoids, Mentha longifolia, tricetin glycosides
Publication DOI: 10.1016/S0367-326X(99)00062-3Journal NLM ID: 16930290RPublisher: Elsevier
Institutions: Phytochemistry and Plant Systematics Department, National Research Centre, Dokki-12311, Cairo, Egypt
Methods: 13C NMR, 1H NMR, TLC, UV, HCl hydrolysis
- Article ID: 11473
Shalaby NMM, Maghraby AS, El-Hagrassy AM "Effect of Daucus carota var. boissieri extracts on immune response of Schistosoma mansoni infected mice" -
Folia Microbiologica 44(4) (1999) 441-448
Isolation and structure elucidation was carried out of flavonoid constituents found in fractionated extracts of the seeds and green leaves of Daucus carota L. var. boissieri (Apiaceae). The flavonoids are mainly apigenin, luteolin, their glycosidic precursors and 2,4,5-trimethoxybenzaldehyde. Fatty acids, hydrocarbons and sterols were identified by GLC. The effect of various carrot extracts on the immune responses of Schistosoma mansoni infected mice was studied. The rate of reduction in worm infestation in mice injected with some fractions indicated a strong protection. Some extracts induced humoral immune response through raising the IgG level at 2, 4 and 6 weeks post-infection as compared with infected control. The phenotypic analysis of the cellular immune response in spleen and mesenteric lymph nodes was accomplished by direct immunofluorescence. The data showed that some extracts stimulated the blastogenesis of CD4+-T splenocytes and mesenteric lymph node cells.
flavonol glycoside, luteolin, apigenin, mesenteric lymph node, praziquantel, worm burden
NCBI PubMed ID: 10983240Publication DOI: 10.1007/bf02903720Journal NLM ID: 0376757Publisher: New York: Springer
Institutions: Laboratory of Natural Products, National Research Centre, Dokki, Cairo, Egypt, Laboratory of Therapeutical Chemistry, National Research Centre, Dokki, Cairo, Egypt
Methods: 1H NMR, GLC, UV, PC
- Article ID: 11476
Kitanaka S, Takido M "Studies on the constituents of the leaves of Cassia torosa Cav. III. The structures of two new flavone glycosides" -
Chemical and Pharmaceutical Bulletin 40(1) (1992) 249-251
Two new flavone glycosides were isolated along with diosmetin, luteolin, and luteolin 7-O-glucoside, from the leaves of Cassia torosa CAV., and their structures were established as diosmetin 3'-O-β-D-glucopyranoside (1) and torosaflavone B 3'-O-β-D-glucopyranoside (2) (diosmetin 6-C-β-D-oliopyranosyl-3'-O-β-D-glucopyranoside) on the basis of spectroscopic and chemical evidence.
2, flavone glycoside, Leguminosae, Cassia torosa, oliose, 6-dideoxyglycoside, torosaflavone B 3'-O-β-D-glucopyranoside, diosmetin 3'-O-β-D-glucopyranoside
Publication DOI: 10.1248/cpb.40.249Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: College of Pharmacy, Nihon University, 7-7 Narashinodai, Funabashi-shi, Chiba 274, Japan
Methods: 13C NMR, 1H NMR, IR, TLC, enzymatic hydrolysis, UV, optical rotation measurement, CD, FD-MS, HCl hydrolysis
- Article ID: 11493
Felser C, Schimmer O "Flavonoid glycosides from Alchemilla speciosa" -
Planta Medica 65(7) (1999) 668-670
The new flavonol glycosides quercetin 3-O-β-(2-O-α-L-rhamnopyranosyl)-glucopyranoside uronic acid and kaempferol 3-O-β-(2-O-α-L-rhamnopyranosyl)-glucopyranoside uronic acid were isolated from the leaves of Alchemilla speciosa Buser together with 13 known flavonol and flavone glycosides and (+)-catechin. The structures were determined by spectroscopic methods.
flavonol glycosides, Alchemilla speciosa, spectroscopic methods
NCBI PubMed ID: 17260291Publication DOI: 10.1055/s-2006-960845Journal NLM ID: 0066751Publisher: George Thieme
Institutions: Institut für Botanik und Pharmazeutische Biologie, Lehrstuhl Pharmazeutische Biologie, Universität Erlangen-Nürnberg, Erlangen, Germany
Methods: 13C NMR, 1H NMR, methylation, TLC, HPLC, UV, acetylation, HCl hydrolysis
- Article ID: 11584
Ozipek M, Saracoglu I, Kojima K, Ogihara Y, Calis I "Fuhsioside, a new phenylethanoid glucoside from Veronica fuhsii" -
Chemical and Pharmaceutical Bulletin 47(4) (1999) 561-562
Fushioside, a new phenylethanoid glucoside, 2-(3,4-dihydroxyphenyl)ethyl 6-O-protocatechuoyl-β-D-glucopyranoside was isolated from the methanolic extract of the aerial parts of Veronica fuhsii along with a known phenylethanoid glycoside, plantamajoside, and a flavone glucoside, luteolin 7-O-glucoside.
phenylethanoid glycoside, Scrophulariaceae, Veronica fuhsii, fuhsioside
Publication DOI: 10.1248/cpb.47.561Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Department of Pharmacognosy, Faculty of Pharmaceutical Sciences, Nagoya City University, Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Nizuho-ku, Nagoya 467-8603 Japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, UV, HMBC, HMQC, COSY
- Article ID: 11588
Yoshikawa M, Morikawa T, Murakami T, Toguchida I, Harima S, Matsuda H "Medicinal flowers. I. Aldose reductase inhibitors and three new eudesmane-type sesquiterpenes, kikkanols A, B, and C, from the flowers of Chrysanthemum indicum L." -
Chemical and Pharmaceutical Bulletin 47(3) (1999) 340-345
The methanolic extract from the flowers of Chrysanthemum indicum L., Chrysanthemi Indici Flos, was found to show inhibitory activity against rat lens aldose reductase. By bioassay-guided separation, the active components, such as flavone and flavone glycosides, were isolated from the extract together with three new eudes-mane-type sesquiterpenes, kikkanols A, B, and C. The structures of kikkanols A, B, and C were elucidated on the basis of chemical and physicochemical evidence, which included application of the modified Mosher's method.
flavonoid, aldose reductase inhibitor, kikkanol, Chrysanthemum indicum, medicinal flower, eudesmane-type sesquiterpene
NCBI PubMed ID: 10212384Publication DOI: 10.1248/cpb.47.340Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Kyoto Pharmaceutical University, Kyoto, Japan
Methods: inhibition studies, TLC, HPLC, HPTLC
- Article ID: 11653
Ma JY, Wang ZT, Xu LS, Xu GJ "A sesquiterpene lactone glucoside from Ixeris denticulata f. pinnatipartita" -
Phytochemistry 50(1) (1999) 113-115
An extract from the entire Ixriss denticulata f. pinnatipartita plant afforded the guaianolide sesquiterpene lactone glucoside, 8β,15-dihydroxy-1(10),3,11(13)-guaiatrien-12,6-olide-15-O-glucopyranoside, along with the known flavonoids luteolin-7-O-glucoside and luteolin-7-O-glucuronide-6'-methyl ester; their structures were determined by spectroscopic methods. Ixerin Y inhibited the growth of human breast cancer MCF7 and MDA468 cell lines.
cytotoxicity, compositae, Ixeris denticulata f. pinnatipartita Kitag, ixerin Y, luteolin-7-O-glucoside, luteolin-7-O-glucuronide-6′-methyl ester
NCBI PubMed ID: 9891935Publication DOI: 10.1016/S0031-9422(98)00452-XJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Pharmanex Shanghai R&D Center, 12th Floor, Zhidao Tower, Shanghai Medical University, 200032 Shanghai, China, Department of Pharmacognosy, China Pharmaceutical University, No. 1 Shennong Rd, Nangjing 210038, China
Methods: 13C NMR, 1H NMR, IR, TLC, UV, EI-MS, cytotoxicity assay, HMBC, HMQC, DEPT, COSY, NOESY, hydrolysis
- Article ID: 11677
Agata I, Sekizaki H, Sakushima A, Nishibe S, Hisada S, Kimura K "Studies on the constituents of medicinal plants in Hokkaido. I. On the whole herb of Swertia tetrapetala Pall." -
Yakugaku Zasshi = Journal of the Pharmaceutical Society of Japan [Japanese] 101(11) (1981) 1067-1071
NCBI PubMed ID: 7343662Publication DOI: 10.1248/yakushi1947.101.11_1067Journal NLM ID: 0413613Publisher: Tokyo: Nihon Yakugakkai
Institutions: Faculty of Pharmaceutical Sciences, Higashi Nippon Gakuen University, Tobetsu, Japan
Methods: 13C NMR, 1H NMR, IR, MS, UV, extraction, column chromatography, melting point determination, derivatization, evaporation
- Article ID: 11742
Calvo MI, Crespo A, Fernández M "Seasonal variations of the iridoids, flavonoids and verbascoside content from Verbena officinalis L" -
Acta Horticulture 516(516) (2000) 169-176
The aim of this work is the quantitative determinations of iridoids, flavonoids and verbascoside by HPLC in leaves of Verbena officinalis during three vegetative periods. The effects of plant age, date of harvest, type of soil, climate, as well as a comparision between two different locations, Ilundain and Lezaun, are been investigated in order to evaluate the development and content of major compounds in Verbena leaves, verbenalin mainly, because it is the active principle. The highest amount of iridoids and flavonoids was found in the leaves during the pre-flowering period. After flowering the total compound content in the leaves decreases, whereas verbascoside content increases. The amount of iridoids and phenolic components are increasing by the years. Verbenalin content is greater in Lezaun than in Ilundain every vegetative cycle.
HPLC, flavonoids, Verbenaceae, verbascoside, Iridoids, Verbena officinalis, experimental field, verbenalin
Publication DOI: 10.17660/ActaHortic.2000.516.20Institutions: Institut de pharmacognosie et phytochimie, Ecole de Pharmacie, Université de Lausanne, Lausanne, Switzerland, Dpto. Farmacia y Tecnologiá Farmaceútica (Farmacognosia), Facultad de Farmacia, Universidad de Navarra, Pamplona, Spain
Methods: HPLC, UV, extraction, derivatization, evaporation
- Article ID: 11932
Ho CT, Wang M, Wei GJ, Huang TC, Huang MT "Chemistry and antioxidative factors in rosemary and sage" -
BioFactors 13(1-4) (2000) 161-166
Rosemary and sage are common spices used in food. In our recent search of cancer chemopreventive agents from spices, the alcohol extracts of rosemary and sage showed strong antumorigenic activities. Rosemary and sage extracts contain active antioxidative factors such as phenolic diterpenes, flavonoids and phenolic acids. Here we discuss chromatographic methods used to separate and purify compounds from these spices and MS and NMR spectrometry to identify the isolated compounds. Several new compounds isolated from sage were determined to be 6-O-caffeoyl-β-D-fructofuranosyl-(2→1)-β-glucopyranoside, 1-O-caffeoyl-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside, 1-O-p-hydroxybenzoyl-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside, 1-O-(3-methyl-2,3,4-trihydroxybutyl)-6-O-feruloyl-β-D-glucopyranoside, 4-hydroxyacetophenone 4-O-[5-O-(3,5-dimethoxy-4-hydroxybenzoyl)-β-D-apiofuranosyl]-(1→2)-β-D-glucopyranoside and 1-O-[2-hydroxy-5-(2-hydroxyethyl)phenyl]-6-O-trans-caffeoyl-β-D-glucopyranoside.
Antioxidant activity, phenolic glycosides, flavonoids, rosemary, sage
NCBI PubMed ID: 11237177Publication DOI: 10.1002/biof.5520130126Journal NLM ID: 8807441Publisher: Oxford; Washington, DC: IRL Press, International Union of Biochemistry
Correspondence: Ho CT
Institutions: Department of Food Science, Rutgers University, New Brunswick, NJ, USA, Department of Food Science and Technology, National Pingtung University of Science and Technology, Pingtung, Taiwan, Laboratory for Cancer Research, College of Pharmacy, Rutgers University, Piscataway, USA
- Article ID: 11941
Hu C, Zhang Y, Kitts DD "Evaluation of antioxidant and prooxidant activities of bamboo Phyllostachys nigra var. henonis leaf extract in vitro" -
Journal of Agricultural and Food Chemistry 48(8) (2000) 3170-3176
Solvent-extracted bamboo leaf extract (BLE) containing chlorogenic acid, caffeic acid, and luteolin 7-glucoside was evaluated in vitro for free radical scavenging and antioxidant activities using a battery of test methods. BLE exhibited a concentration-dependent scavenging activity of DPPH radical. BLE prolonged the lag phase and suppressed the rate of propagation of liposome peroxidation initiated by peroxyl radical induced by 2,2‘-azobis(2-amidinopropane dihydrochloride (AAPH) at 37 °C. BLE also prevented human low-density lipoprotein oxidation, mediated by Cu2+, which was monitored by the lower formation of conjugated diene and fluorescence and a reduced negative charge of apo-B protein. Finally, BLE protected supercoiled DNA strand against scission induced by AAPH-mediated peroxyl radical. Prooxidant activity of BLE was seen in a Cu2+-induced peroxidation of structured phosphatidylcholine liposome, indicating catalytic peroxidation due to a relatively high reducing power of BLE. It was concluded that the BLE has both antioxidant activity and prooxidant activity; the antioxidant activity was attributed to free radical scavenging activity, and the prooxidant activity, albeit minor, resulted from the reducing power of plant phenolics in the presence of transitional metal ions.
Antioxidant, bamboo leaf extract, free radical scavenging, peroxyl radical, prooxidant, reducing power, cupric ion
NCBI PubMed ID: 10956087Publication DOI: 10.1021/jf0001637Journal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: ddkitts@interchange.ubc.ca
Institutions: Food, Nutrition and Health, Faculty of Agricultural Science, University of British Columbia, Vancouver, Canada, Department of Food Science and Nutrition, School of Agricultural Engineering and Food Science, Zhejiang University, Hangzhou, China
Methods: biological assays, HPLC, extraction, evaporation, antioxidant activity test
- Article ID: 11952
Inagaki I, Hisada S, Nishibe S, Sakushima A "Studies on the constituents of the leaves of Trachelospermum asiaticum var. intermedium. I. Isolation of flavones and flavone glycosides" -
Yakugaku Zasshi = Journal of the Pharmaceutical Society of Japan [Japanese] 93(9) (1973) 1231-1234
The methanol extract of the leaves of Trachelospermum asiaticum NAKAI var. intermedium NAKAI was treated (Chart 1) and from the ethyl acetate-soluble fraction, succinic acid, apigenin, luteolin, arctigenin, apigenin 7-glucoside, luteolin 7-glucoside, and luteolin 4'-glucoside were isolated and identified respectively with authentic samples.
flavonoid glucosides, Trachelospermum asiaticum
NCBI PubMed ID: 4797583Publication DOI: 10.1248/yakushi1947.93.9_1231Journal NLM ID: 0413613Publisher: Tokyo: Nihon Yakugakkai
Institutions: Faculty of Pharmaceutical Sciences, Nagoya City University, Nagoya, Japan
Methods: 13C NMR, 1H NMR, IR, TLC, UV, extraction, elemental analysis, column chromatography, melting point determination
- Article ID: 12073
Ivancheva S, Petrova A "A chemosystematic study of eleven Geranium species" -
Biochemical Systematics and Ecology 28(3) (2000) 255-260
The flavonoids of 11 species from six sections (Geranium, Batrachioides, Lucida, Unguiculata, Robertium, Erodioideae) of the genus Geranium have been studied. Quercetin and its derivatives were the most common aglycones with lesser amounts of kaempferol, myricetin and luteolin. Glycosylation was found mainly in the 3 or 4′ positions and to a lesser extent in the 7 position. Chemosystematic relationships are discussed. The occurrence of exudate flavonoids various methyl ether of kaempferol, quercetin and myricetin has been detected in all the 11 species surveyed.
flavonoid glycosides, chemosystematics, Geranium, flavonoid aglycones
Publication DOI: 10.1016/S0305-1978(99)00060-5Journal NLM ID: 0430442Publisher: Pergamon Press
Correspondence: Ivancheva S
Institutions: Institute of Botany, Bulgarian Academy of Sciences, Sofia, Bulgaria
Methods: TLC, extraction, column chromatography, evaporation
- Article ID: 12091
Kamel MS, Mohamed KM, Hassanean HA, Ohtani K, Kasai R, Yamasaki K "Iridoid and megastigmane glycosides from Phlomis aurea" -
Phytochemistry 55(4) (2000) 353-357
From the leaves of Phlomis aurea, two new iridoids of unique structures named 3-epiphlomurin (1) and phlomurin (2), a new megastigmane glucoside phlomuroside (3) and a new benzyl alcohol glycoside having the structure benzyl alcohol-O-β-xylopyranosyl-(1→2)-β-glucopyranoside (4) have been isolated together with four known iridoids auroside, lamiide, 8-epiloganin and ipolamiide, two known phenolic glycosides acteoside (verbascoside) and syringin, one known phenylethanoid glycoside 2-phenylethyl-O-β-xylopyranosyl-(1→2)-β-glucopyranoside, one known lignan liriodendrin and three known flavonoids chrysoeriol-7-O-β-glucopyranoside, acacetin-7-O-β-glucopyranoside and luteolin-7-O-β-glucopyranoside. The structures of the isolated compounds were verified by means of mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectral analyses.
Lamiaceae, Iridoids, Phlomis aurea, megastigmane, benzyl alcohol glycosides
NCBI PubMed ID: 11117884Publication DOI: 10.1016/s0031-9422(00)00331-9Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: mkamel@mailcity.com
Institutions: Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima, Japan, Department of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut, Egypt
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, extraction, optical rotation measurement, column chromatography, MPLC, HR-FAB-MS
- Article ID: 12097
Lin Y-L, Wang W-Y, Kuo Y-H, Chen C-F "Nonsteroidal constituents from Solanum incanum L." -
Journal of the Chinese Chemical Society = Zhongguo hua hsueh hui hui zhi 47(1) (2000) 247-251
Sixteen compounds were isolated from the aerial parts of Solanum incanum L. These compounds included ten flavonoids (1-10), chlorogenic acid (11), adenosine (12), benzyl-O-β-D-xylopyranosyl(1→2)-β-D-glucopyranoside (13), and three phenylalkanoic acids (14-16). The structures were determined from their physical and spectral data. Among these compounds, kaempferol 3-O-(6″′-O-2,5-dihydroxycinnamoyl)-β-D-glucopyranosyl (1→2) β-D-glucopyranoside (10) was identified as a new compound.
flavonoids, aerial parts, Solanum incanum L., ch1orogenic acid, miscellaneous compounds
Publication DOI: 10.1002/jccs.200000029Journal NLM ID: 16210600RPublisher: Taipei: Chinese Chemical Society
Institutions: National Research Institute ofChinese Medicine, Taipei, Taiwan, China, Department ofChemistry, National Taiwan University, Taipei, Taiwan, China
Methods: 13C NMR, 1H NMR, TLC, ESI-MS, HPLC, extraction, derivatization, evaporation, HR-EI-MS
- Article ID: 12099
Lin LZ, He XG, Lindenmaier M, Yang J, Cleary M, Qiu SX, Cordell GA "LC-ESI-MS study of the flavonoid glycoside malonates of red clover (Trifolium pratense)" -
Journal of Agricultural and Food Chemistry 48(2) (2000) 354-365
High-performance liquid chromatography−electrospray ionization−mass spectrometry (LC-ESI-MS) was applied to the analysis of the flavonoids and their glycoside malonates of the flowers and leaves of red clover (Trifolium pratense). Through LC-MS comparative studies on the plant extracts and their malonate-free extracts, ∼20 flavonoid glycoside malonates were detected in the flower extract. Eight were identified as genistin 6‘‘-O-malonate (39), formononetin 7-O-β-D-glucoside 6‘‘-O-malonate (40), biochanin A 7-O-β-D-glucoside 6‘‘-O-malonate (41), trifoside 6‘‘-O-malonate (42), irilone 4‘-O-β-D-glucoside 6‘‘-O-malonate (43), pratensein 7-O-β-D-glucoside 6‘‘-O-malonate (44), isoquercitrin 6‘‘-O-malonate (45), and 3-methylquercetin 7-O-β-D-glucoside 6‘‘-O-malonate (46). About 15 other flavonoids and clovamides were proved to be present in this extract. The study also found that the flowers contained flavones as the major flavonoids, whereas the leaves had isoflavones as the major flavonoids. This is the first detection of the six malonates (39 and 42−46) in the extracts of red clover, and among them, 42, 43, and 46 are new compounds.
flavonoids, Leguminosae, Trifolium pratense, red clover, flavonoid glycoside malonates, clovamides, LC-ESI-MS analysis
NCBI PubMed ID: 10691640Publication DOI: 10.1021/jf991002+Journal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: longze.lin@amtbotanicals.com
Institutions: Research Laboratory of Natural Products Chemistry, A. M. Todd Botanicals, Eugene, USA, Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, The University of Illinois at Chicago, Chicago, IL, USA
Methods: LC-ESI-MS
- Article ID: 12117
Lu K-L, Ku Y-R, Wen K-C, Ho L-K, Chang Y-S "Analysis of flavonoids and coumarins in Ixeris laevigata var. oldhami by HPLC" -
Journal of Liquid Chromatography & Related Technologies 23(16) (2000) 2573-2583
Tao-shang-tsao is the dried entire plant of Ixeris laevigata var. oldhami (Compositae) and a commonly used folk herb in Taiwan. To evaluate the quality of I. laevigata var. oldhami, a simple, rapid, and accurate high-performance liquid chromatographic (HPLC) method was developed for the assay of four flavonoids, apigenin, apigenin-7-O-glucoside, luteolin, and luteolin-7-O-glucoside, and two coumarins, esculetin and esculin. The present HPLC system uses an Inertsil ODS-2 column by gradient elution with acetonitrile and 0.1% (v/v) phosphoric acid as the mobile phase. Ethylparaben was used as an internal standard and detected at 254 nm. Regression equations revealed good linear relationships (correlation coefficients: 0.9998–0.9999) between the peak-area ratios of each constituent to ethylparaben. The relative standard deviations of these six constituents ranged between 0.56–3.04% (intra-day) and 0.79–4.39% (inter-day). The contents of six constituents of I. laevigata var. oldhami in 7 crude drugs have been determined. This study also compared their constituents with those of similar folk herbs, I. chinensis and Taraxacum formosanum, commonly used as an adulterant, by their HPLC chromatograms.
HPLC, coumarins, flavonoids, esculin, esculetin, Ixeris laevigata var. oldhami
Publication DOI: 10.1081/JLC-100100511Journal NLM ID: 9605507Publisher: Monticello, NY: Marcel Dekker
Institutions: Institute of Chinese Pharmaceutical Sciences, China Medical College, Taichung, Taiwan, China, National Laboratories of Foods and Drugs, Department of Health, Executive Yuan, Nankang, Taipei, Taiwan, China, Chung Hwa Institute of Technology, Jen-Teh Hsiang, Taiwan, China, Department and Institute of Pharmacology, National Yang-Ming University, Taipei, Taiwan, China
Methods: HPLC, extraction
- Article ID: 12119
Lu Y, Foo LY "Flavonoid and phenolic glycosides from Salvia officinalis" -
Phytochemistry 55(3) (2000) 263-267
Two novel phenolic glycosides cis-p-coumaric acid 4-O-(2′-O-β-d-apiofuranosyl)-β-d-glucopyranoside and trans-p-coumaric acid 4-O-(2′-O-β-d-apiofuranosyl)-β-d-glucopyranoside were isolated and identified from Salvia officinalis together with 4-hydroxyacetophenone 4-O-(6′-O-β-d-apiofuranosyl)-β-d-glucopyranoside, luteolin 7-O-β-d-glucoside, 7- and 3′-O-β-d-glucuronide, 6-hydroxyluteolin 7-O-β-d-glucoside and 7-O-glucuronide, and 6,8-di-C-β-d-glucosylapigenin (vicenin-2). The luteolin glucuronides and vicenin-2 were identified as new sage constituents.
phenolic glycosides, flavonoids, Labiatae, Salvia offcinalis, cis- and trans-p-coumaric acid 4-O-(2'-O-apiosyl)glucoside
NCBI PubMed ID: 11142853Publication DOI: 10.1016/s0031-9422(00)00309-5Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: y.lu@irl.cri.nz
Institutions: Industrial Research Limited, Lower Hutt, New Zealand
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, HPLC, extraction, HR-ESI-MS, evaporation, centrifugation
- Article ID: 12209
Na M-K, Huong HTT, An RB, Lee S-M, Kim Y-H, Lee J-P, Seong R-S, Lee K-S, Bae K-H "Quality evaluation of Lonicerae Flos" -
Saengyak Hakhoechi = Korean journal of pharmacognosy [Korean] 31(3) (2000) 340-344
Lonicerae Flos, the flower of Lonicera japonica Thunb., has been used as a diuretic, stomachic, antipyretic, analgesic and anti-inflammatory agent in Korea. In order to evaluate the quality of Lonicerae Flos, the method of isolation and quantitative determination of luteolin 7−O−β−D−glucoside as a reference standard compound has been developed. Different specimens of Lonicerae Flos were collected from twenty Korean markets and were analyzed with HPLC using the mobile phase of MeOH-4.5% acetic acid solution (16.5:83.5). The average content of luteolin 7−O−β−D−glucoside from Lonicerae Flos in Korean markets was 0.43±0.34.
Lonicera japonica Thunb.; Lonicerae Flos; luteolin 7−O−β−D−glucoside; HPLC; quantitative determination
Journal NLM ID: 9713418WWW link: https://koreascience.kr/article/JAKO200003041286076.pagePublisher: Seoul : Hanguk Saengyak Hakhoe
Institutions: College of Pharmacy, Chungnam National University, Taejeon, South Korea, College of Pharmacy, Chungbuk National University, Cheongju, South Korea, Korea Food & Drug Administration, Seoul, South Korea
Methods: HPLC
- Article ID: 12292
Pieroni A, Pachaly P, Huang Y, Van Poel B, Vlietinck AJ "Studies on anti-complementary activity of extracts and isolated flavones from Ligustrum vulgare and Phillyrea latifolia leaves (Oleaceae)" -
Journal of Ethnopharmacology 70(3) (2000) 213-217
Polar fractions and flavones isolated from methanolic extracts of the leaves of Ligustrum vulgare and Phillyrea latifolia (Oleaceae), whose popular use as an anti-inflammatory is well-known in Mediterranean historical medicine and ethnobotany, showed significant in vitro complement inhibiting effect on the classical pathway of the complement system. Among the isolated flavonoidic structures, apigenin-7-O-glucoside, apigenin-7-O-rutinoside, luteolin-4'-O-glucoside, luteolin-7-O-glucoside and ligustroflavone presented remarkable activity.
Ligustrum vulgare; Phillyrea latifolia; mediterranean ethnomedicine; flavones; anti-complementary activity
NCBI PubMed ID: 10837985Publication DOI: 10.1016/s0378-8741(99)00169-5Journal NLM ID: 7903310Publisher: Limerick: Elsevier Sequoia
Correspondence: Pieroni A
Institutions: Department of Pharmaceutical Sciences, University of Antwerp (UIA), Antwerp, Belgium, Pharmazeutisches Institut der Rheinischen Friedrich-Wilhelms-Universität Bonn, Bonn, Germany, Dipartimento di Scienza del Suolo e Nutrizione della Pianta, Università degli Studi di Firenze, Firenze, Italy
Methods: inhibition studies, HPLC, extraction
- Article ID: 12293
Pistelli L, Giachi I, Potenza D, Morelli I "A new isoflavone from Genista corsica" -
Journal of Natural Products 63(4) (2000) 504-506
A new isoflavone (1), dihydroisoderrondiol [(3"S,4"R)-5,7,3",4"-tetrahydroxy-2",2"-dimethyl-3",4"-dihydropyrano(5",6";3",4")isoflavone], was isolated from aerial parts of Genista corsica, together with 11 previously known compounds [daidzein, isoprunetin, isoderrone (2), ficuisoflavone (3), luteolin, luteolin 4'-O-β-glucoside, luteolin 7-O-β-glucoside, taxifolin, 5-methoxytaxifolin, sucrose, and D-pinitol]. The structure of 1 was elucidated by spectroscopic methods.
flavonoid glycosides, Genista corsica, dihydroisoderrondiol
NCBI PubMed ID: 10785424Publication DOI: 10.1021/np990282kJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: Pistelli L
Institutions: Dipartimento di Chimica Organica e Industriale, Universitá di Milano, Milano, Italy, Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Pisa, Italy
Methods: 13C NMR, 1H NMR, TLC, ESI-MS, HPLC, extraction, derivatization, evaporation, HR-EI-MS
- Article ID: 12341
Samuelsen AB "The traditional uses, chemical constituents and biological activities of Plantago major L. A review" -
Journal of Ethnopharmacology 71(1-2) (2000) 1-21
Plantago major L. leaves have been used as a wound healing remedy for centuries in almost all parts of the world and in the treatment of a number of diseases apart from wound healing. These include diseases related to the skin, respiratory organs, digestive organs, reproduction, the circulation, against cancer, for pain relief and against infections. P. major contains biologically active compounds such as polysaccharides, lipids, caffeic acid derivatives, flavonoids, iridoid glycosides and terpenoids. Alkaloids and some organic acids have also been detected. A range of biological activities has been found from plant extracts including wound healing activity, anti-inflammatory, analgesic, antioxidant, weak antibiotic, immuno modulating and antiulcerogenic activity. Some of these effects may attribute to the use of this plant in folk medicine.
traditional uses; chemical constituents; biological activities; Plantago major L
NCBI PubMed ID: 10904143Publication DOI: 10.1016/s0378-8741(00)00212-9Journal NLM ID: 7903310Publisher: Limerick: Elsevier Sequoia
Correspondence: a.b.samuelsen@farmasi.uio.no
Institutions: Department of Pharmacognosy, School of Pharmacy, University of Oslo, Oslo, Norway
- Article ID: 12399
Smith GJ, Thomsen SJ, Markham KR, Andary C, Cardon D "The photostabilities of naturally occurring 5-hydroxyflavones, flavonols, their glycosides and their aluminium complexes" -
Journal of Photochemistry and Photobiology. A, Chemistry 136(1-2) (2000) 87-91
The photostabilities of luteolin, in solution, in the presence of aluminium ions, and deposited on a cellulosic substrate have been determined and compared with those of quercetin and other 5-hydroxyflavonols and their 3-O-glycosides. In aqueous methanol solution, luteolin and flavonol 3-glycosides exhibited no degradation over periods of up to 15 h of UV irradiation. However, the flavonols studied were all found to degrade and their relative photostabilities correlate with their redox potentials. Quercetin was the least stable. In the presence of aluminium ions, all the flavonoids, including luteolin, were degraded by UV irradiation. In contrast to the absorption spectra in dilute solution, the reflectance spectra of both quercetin and luteolin deposited on a cellulosic substrate exhibited strong absorptions beyond 400 nm. On this substrate these flavonoids displayed the characteristic yellow colour associated with flavonoids in some environments. Although the quercetin yellow faded rapidly on exposure to UV radiation, the colour of luteolin darkened. This was due to the formation of a photoproduct absorbing maximally at 450 nm. The relevance of these observations to cellulosic dyeing and flower colouration are discussed.
5-hydroxyflavones; flavonols; luteolin; quercetin
Publication DOI: 10.1016/S1010-6030(00)00320-8Journal NLM ID: 9883240Publisher: Lausanne, Switzerland: Elsevier Sequoia
Institutions: New Zealand Institute for Industrial Research, Lower Hutt, New Zealand, Laboratoire de Botanique, Phytochimie et Mycologie, Université Montpellier 1, Montpellier, France, CNRS, Lyon, France
Methods: UV, spectrophotometry
- Article ID: 12445
Tattini M, Gravano E, Pinelli P, Mulinacci N, Romani A "Flavonoids accumulate in leaves and glandular trichomes of Phillyrea latifolia exposed to excess solar radiation" -
New Phytologist 148(1) (2000) 69-77
Experiments were conducted on Phillyrea latifolia plants grown under a dense overstorey of Pinus pinea (shade plants) or on seashore dunes (sun plants) in a coastal area of Tuscany (42° 46′ N, 10° 53′ E). Total integrated photon flux densities averaged 1.67 and 61.4 m mol/m^2/d for shade and sun sites, respectively. A leaf morphological–structural analysis, a qualitative and quantitative analysis of phenylpropanoids of leaf tissue and leaf surface, and a histochemical localization of flavonoids were conducted. The area of sun leaves reached 57% of that of shade leaves, whereas leaf angle (β), sclerophylly index (ratio of leaf d. wt:leaf area), and trichome frequency (trichome number mm−2 ) were markedly greater in leaves exposed to full solar radiation than in leaves acclimated to shade. The total thickness of sun leaves was 78% higher than that of shade leaves, mostly owing to a greater development of both palisade parenchyma and spongy mesophyll. The concentration, but not the composition, of leaf tissue phenylpropanoids varied significantly between sun and shade leaves, with a marked increase in flavonoid glycosides in sun leaves. Flavonoids occurred almost exclusively in the upper epidermal cells of shade leaves. By contrast, flavonoids largely accumulated in the upper and lower epidermis, as well as in the mesophyll tissue of leaves that were acclimated to full sunlight. Flavonoid glycosides were found exclusively in the secretory products of glandular trichomes of P. latifolia leaves exposed to high levels of light; luteolin 7-O- glucoside and quercetin 3-O-rutinoside were the major constituents. By contrast, verbascoside and an unidentified caffeic acid derivative constituted 72% of total phenylpropanoids secreted by glandular trichomes of shade leaves, whereas they were not detected in glandular trichomes of sun leaves. These findings suggest that the light-induced synthesis of flavonoids in glandular trichomes of P. latifolia probably occurs in situ and concomitantly inactivates other branch pathways of the general phenylpropanoid metabolism. This is the first report of the key role of glandular trichomes and of flavonoid glycosides in the integrated mechanisms of acclimation of P. latifolia to excess light.
flavonol glycosides, Oleaceae, phenylpropanoids, fluorescence microscopy, glandular trichomes
NCBI PubMed ID: 33863030Publication DOI: 10.1046/j.1469-8137.2000.00743.xJournal NLM ID: 9882884Publisher: Blackwell Publishing
Correspondence: tattini@ipsl.fi.cnr.it
Institutions: Dipartimento di Scienze Farmaceutiche, Università di Firenze, Florence, Italy, Istituto sulla Propagazione delle Specie Legnose - Consiglio Nazionale delle Ricerche, Scandicci, Italy, Dipartimento di Biologia Vegetale, Università di Firenze, Florence, Italy
Methods: ESI-MS, HPLC, UV, extraction, HPTLC, HPLC-MS, spectrophotometry
- Article ID: 12472
Upson TM, J Grayer R, Greenham JR, A Williams C, Al-Ghamdi F, Chen F "Leaf flavonoids as systematic characters in the genera Lavandula and Sabaudia" -
Biochemical Systematics and Ecology 28(10) (2000) 991-1007
A comprehensive survey of the leaf flavonoids of the genus Lavandula and the related Sabaudia group was carried out using two-dimensional paper chromatography and high-performance liquid chromatography. The flavonoid patterns obtained were found to be systematically informative at the infrageneric level. Three main groupings were identified: the first containing sections Lavandula, Dentata and Stoechas characterised by the accumulation of flavone 7-glycosides; the second containing sections Pterostoechas, Subnuda and Chaetostachys characterised by the accumulation of 8-hydroxylated flavone 7-and 8-glycosides; the third encompassing the Sabaudia group and accumulating both flavone and 8-hydroxylated flavone 7- glycosides. Such a grouping of taxa is congruent with data from other disciplines, although it is not recognised in any present classifications. The taxonomic and evolutionary implications of the flavonoid data are discussed.
Lavandula; Sabaudia; lavender; Lamiaceae; flavonoids; chemotaxonomy
NCBI PubMed ID: 10996263Publication DOI: 10.1016/s0305-1978(00)00013-2Journal NLM ID: 0430442Publisher: Pergamon Press
Correspondence: christine.williams@reading.ac.uk
Institutions: Department of Botany, University of Reading, Reading, UK, Jodrell Laboratory, Royal Botanic Gardens, Richmond, UK
Methods: HPLC, UV, extraction, paper electrophoresis, PPC, 2D paper chromatography
- Article ID: 12594
Pieroni A, Pachaly P "Isolation and structure elucidation of ligustroflavone, a new apigenin triglycoside from the leaves of Ligustrum vulgare L." -
Die Pharmazie 55(1) (2000) 78-80
A new flavone, apigenin-7-O-β-(2",6"-di-α-rhamnopyranosyl)-glucopyranoside , named ligustroflavone, was isolated from the leaves of common privet (Ligustrum vulgare L., Oleaceae), whose popular use was well known in the Mediterranean historical medicine and ethnomedicine as anti-inflammatory. The structures of other five apigenin and luteolin derivates, isolated from the polar fractions of the methanolic leaf extracts, were elucidated.
NCBI PubMed ID: 10683879Journal NLM ID: 9800766Publisher: Eschborn: Govi-Verlag Pharmazautischer Verlag
Correspondence: Pieroni A
Institutions: Pharmaceutical Institute, University of Bonn, Bonn, Germany
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, enzymatic hydrolysis, acid hydrolysis, HPLC, optical rotation measurement, HR-FAB-MS
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6. Compound ID: 26214
Structure type: monomer
Compound class: glycoside, flavonoid glycoside, flavone glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_423153,IEDB_613439
The structure is contained in the following publication(s):
- Article ID: 10482
Igile GO, Oleszek W, Jurzysta M, Burda S, Fafunso M, Fasanmade AA "Flavonoids from Vernonia amygdalina and their antioxidant activities" -
Journal of Agricultural and Food Chemistry 42 (1994) 2445-2448
Journal NLM ID: 0374755Publisher: American Chemical Society
- Article ID: 10511
Bucar F, Kartnig T "Flavone glucuronides of Lycopus virginicus" -
Planta Medica 61 (1995) 378-380
From the ethanolic extract of the aerial parts of Lycopus virginicus (L.) Michx. (Lamiaceae) the 7-O-β-D-glucuronides of apigenin, acacetin, and luteolin as well as the methyl ester of apigenin 7-O-β-D-glucuronide could be isolated. Quantification of luteolin 7-O-β-D-glucuronide by HPLC in crude methanolic extracts from L. virginicus, L. europaeus, and L. exaltatus showed contents of 0.017-0.22%.
NCBI PubMed ID: 17238089Publication DOI: 10.1055/s-2006-958111Journal NLM ID: 0066751Publisher: George Thieme
- Article ID: 11436
Huang Y, De Bruyne T, Apers S, Ma Y, Claeys M, Pieters L, Vlietinck A "Flavonoid glucuronides from Picria fel-terrae" -
Phytochemistry 52(8) (1999) 1701-1703
Three flavonoid glucuronides are reported from a n-BuOH extract of Picria fel-terrae (Scrophulariaceae). The structures were established by UV, one- and two-dimensional NMR and mass spectrometry as apigenin 7-O-β-glucuronide, luteolin 7-O-β-glucuronide and apigenin 7-O-β-(2"-O-α-rhamnosyl)glucuronide, the latter one being a new compound.
flavonoid glycosides, Scrophulariaceae, Picria fel-terrae, flavonoid glucuronides, apigenin 7-O-β-glucuronide, luteolin 7-O-β-glucuronide, apigenin 7-O-β-(2″-O-α-rhamnosyl)glucuronide
Publication DOI: 10.1016/S0031-9422(99)00242-3Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Pharmaceutical Sciences, University of Antwerp, Universiteitsplein 1, B-2610 Antwerp, Belgium
Methods: 13C NMR, 1H NMR, FAB-MS, TLC, acid hydrolysis, UV, PC, HMBC, COSY, HSQC
- Article ID: 11588
Yoshikawa M, Morikawa T, Murakami T, Toguchida I, Harima S, Matsuda H "Medicinal flowers. I. Aldose reductase inhibitors and three new eudesmane-type sesquiterpenes, kikkanols A, B, and C, from the flowers of Chrysanthemum indicum L." -
Chemical and Pharmaceutical Bulletin 47(3) (1999) 340-345
The methanolic extract from the flowers of Chrysanthemum indicum L., Chrysanthemi Indici Flos, was found to show inhibitory activity against rat lens aldose reductase. By bioassay-guided separation, the active components, such as flavone and flavone glycosides, were isolated from the extract together with three new eudes-mane-type sesquiterpenes, kikkanols A, B, and C. The structures of kikkanols A, B, and C were elucidated on the basis of chemical and physicochemical evidence, which included application of the modified Mosher's method.
flavonoid, aldose reductase inhibitor, kikkanol, Chrysanthemum indicum, medicinal flower, eudesmane-type sesquiterpene
NCBI PubMed ID: 10212384Publication DOI: 10.1248/cpb.47.340Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Kyoto Pharmaceutical University, Kyoto, Japan
Methods: inhibition studies, TLC, HPLC, HPTLC
- Article ID: 12119
Lu Y, Foo LY "Flavonoid and phenolic glycosides from Salvia officinalis" -
Phytochemistry 55(3) (2000) 263-267
Two novel phenolic glycosides cis-p-coumaric acid 4-O-(2′-O-β-d-apiofuranosyl)-β-d-glucopyranoside and trans-p-coumaric acid 4-O-(2′-O-β-d-apiofuranosyl)-β-d-glucopyranoside were isolated and identified from Salvia officinalis together with 4-hydroxyacetophenone 4-O-(6′-O-β-d-apiofuranosyl)-β-d-glucopyranoside, luteolin 7-O-β-d-glucoside, 7- and 3′-O-β-d-glucuronide, 6-hydroxyluteolin 7-O-β-d-glucoside and 7-O-glucuronide, and 6,8-di-C-β-d-glucosylapigenin (vicenin-2). The luteolin glucuronides and vicenin-2 were identified as new sage constituents.
phenolic glycosides, flavonoids, Labiatae, Salvia offcinalis, cis- and trans-p-coumaric acid 4-O-(2'-O-apiosyl)glucoside
NCBI PubMed ID: 11142853Publication DOI: 10.1016/s0031-9422(00)00309-5Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: y.lu@irl.cri.nz
Institutions: Industrial Research Limited, Lower Hutt, New Zealand
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, HPLC, extraction, HR-ESI-MS, evaporation, centrifugation
- Article ID: 12472
Upson TM, J Grayer R, Greenham JR, A Williams C, Al-Ghamdi F, Chen F "Leaf flavonoids as systematic characters in the genera Lavandula and Sabaudia" -
Biochemical Systematics and Ecology 28(10) (2000) 991-1007
A comprehensive survey of the leaf flavonoids of the genus Lavandula and the related Sabaudia group was carried out using two-dimensional paper chromatography and high-performance liquid chromatography. The flavonoid patterns obtained were found to be systematically informative at the infrageneric level. Three main groupings were identified: the first containing sections Lavandula, Dentata and Stoechas characterised by the accumulation of flavone 7-glycosides; the second containing sections Pterostoechas, Subnuda and Chaetostachys characterised by the accumulation of 8-hydroxylated flavone 7-and 8-glycosides; the third encompassing the Sabaudia group and accumulating both flavone and 8-hydroxylated flavone 7- glycosides. Such a grouping of taxa is congruent with data from other disciplines, although it is not recognised in any present classifications. The taxonomic and evolutionary implications of the flavonoid data are discussed.
Lavandula; Sabaudia; lavender; Lamiaceae; flavonoids; chemotaxonomy
NCBI PubMed ID: 10996263Publication DOI: 10.1016/s0305-1978(00)00013-2Journal NLM ID: 0430442Publisher: Pergamon Press
Correspondence: christine.williams@reading.ac.uk
Institutions: Department of Botany, University of Reading, Reading, UK, Jodrell Laboratory, Royal Botanic Gardens, Richmond, UK
Methods: HPLC, UV, extraction, paper electrophoresis, PPC, 2D paper chromatography
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7. Compound ID: 26253
Structure type: monomer
; 610 [M+]
Trivial name: lutonarin
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_613439,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10504
Krauze-Baranowska M, Cisowski W "Flavone C-glycosides from Bryonia alba and B-dioica" -
Phytochemistry 39 (1995) 727-729
Lutonarin was isolated from Bryonia alba and B. dioica. Five further C-glycosides: vitexin, isovitexin, isoorientin, saponarin were isolated from B. dioica together with saponarin caffeic ester, a new natural product.
Cucurbitaceae, flavone C-glycosides, Bryonia alba, Bryonia dioica, apigenin 6-C-glucoside-7-0-(6″-caffeoyl)glucoside)
Publication DOI: 10.1016/0031-9422(95)00069-JJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Pharmacognosy, Medical University, Gdańsk, Poland
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8. Compound ID: 26277
Structure type: oligomer
Trivial name: lonicerin, veronicastroside, veronicastroside
Compound class: glycoside, flavonoid glycoside, flavone glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_613439,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10513
Kraut L, Scherer B, Mues R, Sim-Sim M "Flavonoids from some Frullania species (Hepaticae)" -
Zeitschrift für Naturforschung. C, Journal of Biosciences 50 (1995) 345-352
Journal NLM ID: 8912155Publisher: Verlag der Zeitschrift für Naturforschung
- Article ID: 11466
Sharaf M, El-Ansari MA, Saleh NAM "Flavone glycosides from Mentha longifolia" -
Fitoterapia 70(5) (1999) 478-483
In addition to isoorientin, vicenin-2, hypolaetin, lucenin-1, luteolin 7-O-glucoside and 7-O-neohesperidoside, the aerial parts of Mentha longifolia yielded three new flavonoids, identified as tricetin 7-O-methylether 3'-O glucoside 5'-O-rhamnoside (1), tricetin 3'-O glucoside 5'-O-rhamnoside (2) and tricetin 3'-O-rhamnosyl-(1→4)-rhamnoside (3).
flavonoids, Mentha longifolia, tricetin glycosides
Publication DOI: 10.1016/S0367-326X(99)00062-3Journal NLM ID: 16930290RPublisher: Elsevier
Institutions: Phytochemistry and Plant Systematics Department, National Research Centre, Dokki-12311, Cairo, Egypt
Methods: 13C NMR, 1H NMR, TLC, UV, HCl hydrolysis
- Article ID: 11953
Inagaki I, Sakushima A, Hisada S, Nishibe S, Morita N "Comparison of lonicerin and veronicastroside" -
Yakugaku Zasshi = Journal of the Pharmaceutical Society of Japan [Japanese] 94(4) (1974) 524-525
A direct comparison was made between lonicerin (luteolin 7-rhamnoglucoside) from Lonicera japonica THUNB. (Caprifoliaceae) and veronicastroside (luteolin 7-neohesperidoside) from Trachelospermum asiaticum NAKAI var. intermedium NAKAI (Apocynaceae) and it was found that they are identical in all respects. Therefore, lonicerin is luteolin 7-neohesperidoside
identification, flavonoid glycosides, lonicerin, veronicastroside
NCBI PubMed ID: 4473018Publication DOI: 10.1248/yakushi1947.94.4_524Journal NLM ID: 0413613Publisher: Tokyo: Nihon Yakugakkai
Institutions: Faculty of Pharmaceutical Sciences, Nagoya City University, Nagoya, Japan
Methods: IR, TLC, paper chromatography, UV, melting point determination
- Article ID: 12326
Sakushima A, Hisada S, Nishibe S, Inagaki I "Studies on the constituents of the leaves of Trachelospermum asiaticum var. intermedium. II. isolation and structure of a new flavone glycoside" -
Yakugaku Zasshi = Journal of the Pharmaceutical Society of Japan [Japanese] 93(9) (1973) 1127-1130
After treating the methanol extractive of the leaves of Trachelospermum asiaticum NAKAI var.intermedium NAKAI with ethyl acetate, the mother liquor was extracted with butanol. Three flavone diglycosides (VIII, IX, and X) were isolated from butanol extract by column chromatography over silica gel. VIII and X were respectively identified with the authentic rhoifolin and luteolin 7-neohesperidoside (veronicastroside) in all respects. IX is a new compound, which was elucidated as apigenin 7-gentiobioside.
NCBI PubMed ID: 4797566Publication DOI: 10.1248/yakushi1947.93.9_1127Journal NLM ID: 0413613Publisher: Tokyo: Nihon Yakugakkai
Institutions: Faculty of Pharmaceutical Sciences, Nagoya City University, Nagoya, Japan
Methods: C3
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9. Compound ID: 26327
Structure type: monomer
; 449 [M+H]+
Trivial name: glucoluteolin
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_613439,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10543
Kubo M, Sasaki H, Endo T, Taguchi H, Yosioka I "The constituents of Schizonepeta tenuifolia BRIQ. II. Structure of a new monoterpene glucoside, Schizonepetoside C" -
Chemical and Pharmaceutical Bulletin 34(8) (1987) 3097-3101
Besides three known flavonoid glycosides, a new monoterpene glucoside named schizonepetoside C (3) was isolated from the spikes of Schizonepeta tenuifolia BRIQ. (Labiatae), as an amorphous powder. The structure of 3 was established as (1S,4E)-9-O-β-D-glucopyranosyl-p-menth-4(8)-en-3-one by chemical methods and spectral analyses.
13C NMR, Labiatae, monoterpene glucoside, Schizonepeta tenuifolia, schizonepetoside C, (1S, 4E)-9-O-β-D-glucopyranosyl-p-menth-4(8)-en-3-one, apigenin-7-O-β-D-glucoside, luteolin-7-O-β-D-glucoside, hesperidin
Publication DOI: 10.1248/cpb.34.3097Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Tsumura Laboratory, Japan
Methods: 13C NMR, 1H NMR, IR, TLC, HPLC, UV, enzymatic digestion, reduction, FD-MS, acetylation analysis
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10. Compound ID: 26402
Structure type: monomer
Trivial name: lutonarin
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_613439,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10566
Krauze-Baranowska M, Cisowski W "High-performance liquid chromatographic determination of flavone C-glycosides in some species of the Cucurbitaceae family" -
Journal of Chromatography A 675 (1994) 240-243
Flavonoid complexes occurring in the medicinal plants Bryonia alba, Bryonia dioica and Lagenaria siceraria were found to be flavone C-glycosides. Flavonoids of these species were compared by HPLC and separation conditions were elaborated for C-glycosides using isocratic and gradient elution. The content of the major C-glycoside, saponarin, was determined. The highest saponarin level (2.481%) was found in Bryonia dioica.
Publication DOI: 10.1016/0021-9673(94)85278-2Journal NLM ID: 9318488Publisher: Amsterdam; New York: Elsevier
Institutions: Department of Pharmacognosy, Medical Academy, Gdańsk, Poland
Methods: HPLC, UV
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11. Compound ID: 26408
Structure type: monomer
Trivial name: isoorientin
Compound class: glycoside
Contained glycoepitopes: IEDB_613439
The structure is contained in the following publication(s):
- Article ID: 10566
Krauze-Baranowska M, Cisowski W "High-performance liquid chromatographic determination of flavone C-glycosides in some species of the Cucurbitaceae family" -
Journal of Chromatography A 675 (1994) 240-243
Flavonoid complexes occurring in the medicinal plants Bryonia alba, Bryonia dioica and Lagenaria siceraria were found to be flavone C-glycosides. Flavonoids of these species were compared by HPLC and separation conditions were elaborated for C-glycosides using isocratic and gradient elution. The content of the major C-glycoside, saponarin, was determined. The highest saponarin level (2.481%) was found in Bryonia dioica.
Publication DOI: 10.1016/0021-9673(94)85278-2Journal NLM ID: 9318488Publisher: Amsterdam; New York: Elsevier
Institutions: Department of Pharmacognosy, Medical Academy, Gdańsk, Poland
Methods: HPLC, UV
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12. Compound ID: 26444
Structure type: monomer
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_613439,IEDB_983931,SB_192,SB_61
The structure is contained in the following publication(s):
- Article ID: 10583
Hu CQ, Chen K, Shi Q, Kilkuskie RE, Cheng YC, Lee KH "Anti-aids agents, 10. Acacetin-7-O-β-D-galactopyranoside, an anti-HIV principle from Chrysanthemum morifolium and a structure-activity correlation with some related flavonoids" -
Journal of Natural Products 57 (1994) 42-51
An active anti-HIV principle, acacetin-7-O-β-D-galactopyranoside, has been isolated from Chrysanthemum morifolium. Seven additional flavonoids isolated from this plant, 13 known related flavonoids, and 14 synthetic flavonoids were also evaluated as inhibitors of HIV replication in H9 cells. A known flavone, chrysin, was found to be the most promising compound in this series. Flavonoids with hydroxy groups at C-5 and C-7 and with a C-2-C-3 double bond were more potent inhibitors of HIV growth. In general, the presence of substituents (hydroxyl and halogen) in the B-ring increased toxicity and/or decreased activity.
NCBI PubMed ID: 8158164Publication DOI: 10.1021/np50103a006Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Institutions: Natural Products Laboratory, School of Pharmacy, University of North Carolina, Chapel Hill 27599
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13. Compound ID: 26445
Structure type: monomer
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_613439,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10583
Hu CQ, Chen K, Shi Q, Kilkuskie RE, Cheng YC, Lee KH "Anti-aids agents, 10. Acacetin-7-O-β-D-galactopyranoside, an anti-HIV principle from Chrysanthemum morifolium and a structure-activity correlation with some related flavonoids" -
Journal of Natural Products 57 (1994) 42-51
An active anti-HIV principle, acacetin-7-O-β-D-galactopyranoside, has been isolated from Chrysanthemum morifolium. Seven additional flavonoids isolated from this plant, 13 known related flavonoids, and 14 synthetic flavonoids were also evaluated as inhibitors of HIV replication in H9 cells. A known flavone, chrysin, was found to be the most promising compound in this series. Flavonoids with hydroxy groups at C-5 and C-7 and with a C-2-C-3 double bond were more potent inhibitors of HIV growth. In general, the presence of substituents (hydroxyl and halogen) in the B-ring increased toxicity and/or decreased activity.
NCBI PubMed ID: 8158164Publication DOI: 10.1021/np50103a006Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Institutions: Natural Products Laboratory, School of Pharmacy, University of North Carolina, Chapel Hill 27599
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14. Compound ID: 26495
Structure type: monomer
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_613439,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10604
Tiller SA, Parry AD, Edwards R "Changes in the accumulation of flavonoid and isoflavonoid conjugates associated with plant age and nodulation in alfalfa (Medicago sativa)" -
Physiologia Plantarum 91 (1994) 27-36
Medicarpin 3-O-glucoside-6″-O-malonate (MGM), formononetin 7-O-glucoside-6″-O-malonate (FGM) and two glycosides of coumestrol (CG), one of which was characterised as a malonylated glucoside, have been identified as major isoflavonoid metabolites in the roots of healthy alfalfa (Medicago sativa) plants. Foliage contained a conjugate of the flavonoid apigenin, very low levels of medicarpin and MGM, and depending on the cultivar studied, formononetin and FGM. In the foliage the isoflavonoids were restricted to the stems. Seeds contained conjugates of quercetin, luteolin and 7,4′-dihydroxyflavone but no isoflavonoid conjugates. When alfalfa plants were grown under controlled conditions, isoflavonoid conjugates were first observed in the roots 24 h after emerging, and continued to accumulate as the plants matured over a 57 day period. Inoculating the plants with a commercial formulation of Rhizobium meliloti (Nodulaid) reduced FGM accumulation in the roots but did not affect MGM or CG content. Under field conditions plants accumulated higher concentrations of the isoflavonoid conjugates in both leaves and roots than plants grown under controlled conditions. Field-grown plants which were not inoculated with Nodulaid contained higher levels of both MGM and FGM in the roots than nodulated plants. The conjugation of isoflavonoids in alfalfa cell cultures resembled that of the roots in that they accumulated FGM and MGM as major metabolites. However, cultures accumulated a higher proportion of their conjugated isoflavonoids as MGM and formononetin glucoside than did the roots and did not synthesise coumestrol. Comparisons with clover species revealed that FGM and MGM were common metabolites in forage legumes but alfalfa was unusual in having negligible levels of isoflavonoid conjugates in the foliage. Our results clarify the nature and distribution of isoflavonoid conjugates in alfalfa and demonstrate that their accumulation is regulated in response to both plant age and nodulation.
nodulation, development, alfalfa, isoflavonoid conjugates, Medicago sativa
Publication DOI: 10.1111/j.1399-3054.1994.tb00655.xJournal NLM ID: 1256322Publisher: Copenhagen: Scandinavian Society For Plant Physiology
Institutions: Department of Biological Sciences, University of Durham, Durham, UK
Methods: 1H NMR, TLC, HPLC, UV, enzymatic digestion
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15. Compound ID: 26556
Structure type: monomer
; 461 [M-H]-
Compound class: glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_423153,IEDB_613439
The structure is contained in the following publication(s):
- Article ID: 10620
Okamura N, Haraguchi H, Hashimoto K, Yagi A "Flavonoids in Rosmarinus officinalis leaves" -
Phytochemistry 37 (1994) 1463-1466
Three new flavonoid glucuronides, luteolin 3'-O-β-D-glucuronide, luteolin 3'-O-(4"-O-acetyl)-β-D-glucuronide, and luteolin 3'-O-(3"-O-acetyl)-β-D-glucuronide, together with hesperidin, were isolated from 50% aqueous MeOH extract of the leaves of rosemary. The structures were established by chemical and spectroscopic methods. Their antioxidant activities were evaluated by a ferric thiocyanate method with hesperidin showing the greatest activity.
Antioxidant activity, flavonoid glycosides, Labiatae, hesperidin, Rosmarinus officinalis, rosemary, luteolin 3′-O-β-d-glucuronide, luteolin 3′-O-(4″-O-acetyl)-β-d-glucuronide, luteolin 3′-O-(3″-O-acetyl)-β-d-glucuronide
NCBI PubMed ID: 7765765Publication DOI: 10.1016/S0031-9422(00)90434-5Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Hiroshima, Japan, Engineering, Fukuyama University, Fukuyama, Hiroshima, Japan
Methods: 13C NMR, 1H NMR, FAB-MS, TLC, acid hydrolysis, alkaline hydrolysis, UV, enzymatic digestion, CC
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