Show legend Show as text

Structure type: monomer ; 471.3 [M+Na]+
C₂₁H₂₀O₁₁
Compound class: phenolic glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 8194
  Lin S, Zhu Q, Wen L, Yang B, Jiang G, Gao H, Chen F, Jiang Y "Production of quercetin, kaempferol and their glycosidic derivatives from the aqueous-organic extracted residue of litchi pericarp with Aspergillus awamori" - Food Chemistry 145 (2014) 220-227
  

  Our previous work exhibited Aspergillus awamori fermentation of the litchi pericarp increased significantly antioxidant activity and DNA protection effect. In this present study, the litchi pericarp and its aqueous-organic extracted residues were fermented by A. awamori in order to elucidate the enhanced beneficial effects. The study identified that rutin which present in litchi pericarp could be deglycosylated to form quercetin and quercetin-3-glucoside after the fermentation. Application the standard compounds (rutin, quercetin 3-glucoside, quercetin, kaempferol-3-glucoside and kaempferol) further revealed the effective biotransformation by A. awamori fermentation. It was hypothesised that rutin was initially dehydroxylated to form kaempferol-3-rutinoside and then deglycosylated to form kaempferol-3-glucoside and kaempferol. To our best knowledge, it is the first report on dehydroxylated effect of polyphenols caused by A. awamori fermentation. Thus, A. awamori fermentation can provide an effective way to produce health benefiting value-added products from litchi pericarp in food industry.

  quercetin, Aspergillus awamori, dehydroxylation, kaempferol, litchi, pericarp

  NCBI PubMed ID: 24128471
  Publication DOI: 10.1016/j.foodchem.2013.08.048
  Journal NLM ID: 7702639
  Publisher: Elsevier Applied Science Publishers
  Correspondence: Jiang Y
  Institutions: University of Chinese Academy of Sciences, Beijing, China, Key Laboratory of Plant Resource Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, China, Food Science Institute, Zhejiang Academy of Agricultural Sciences, Hangzhou, China, Department of Food, Nutrition and Packaging Sciences, Clemson University, Clemson, SC, USA
  Methods: 13C NMR, 1H NMR, ESI-MS, GC, UV, statistical analysis, radical scavenging assay, HPLC-DAD, TFA hydrolysis
  
   
  
  Litchi chinensis, Aspergillus awamori GIM 3.4
  CSDB ID 47474 (all data & tools)

Show legend Show as text

Structure type: monomer ; 447 [M-H]-
Trivial name: astragalin
Compound class: flavonol glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 8284
  Zi J, Valiente J, Zeng J, Zhan J "Metabolism of quercetin by Cunninghamella elegans ATCC 9245" - Journal of Bioscience and Bioengineering 112(4) (2011) 360-362
  

  Incubation of quercetin with Cunninghamella elegans ATCC 9245 yielded three metabolites, including quercetin 3-O-β-D-glucopyranoside, kaempferol 3-O-β-D-glucopyranoside and isorhamnetin 3-O-β-D-glucopyranoside. Glucosylation, O-methylation and dehydroxylation were involved in the process, among which dehydroxylation has never been found in Cunninghamella. Quercetin was completely metabolized in 72 h.

  methylation, glucosylation, quercetin, Cunninghamella elegans, dehydroxylation

  NCBI PubMed ID: 21742550
  Publication DOI: 10.1016/j.jbiosc.2011.06.006
  Journal NLM ID: 100888800
  Publisher: Osaka, Japan, Amsterdam, The Netherlands: Society for Bioscience and Bioengineering
  Correspondence: Zhan J
  Institutions: Department of Biological Engineering, Utah State University, Logan, USA
  Methods: 13C NMR, 1H NMR, HPLC, UV, extraction, LC-MS
  
   
  
  Cunninghamella elegans ATCC 9245
  CSDB ID 46694 (all data & tools)
• Article ID: 10859
  Mekkawy SE, Meselhy MR, Kusumoto IT, Kadota S, Hattori M, Namba T "Inhibitory effects of Egyptian folk medicines on human immunodeficiency virus (HIV) reverse transcriptase" - Chemical and Pharmaceutical Bulletin 43(4) (1995) 641-648
  

  Extracts of 41 medicinal plants used in Egyptian folk medicine were screened for their inhibitory effects on human immunodeficiency virus-1 reverse transcriptase. The extracts of fruits of Phyllanthus emblica, Quercus pedunculata, Rumex cyprius, Terminalia bellerica, Terminalia chebula and Terminalia horrida showed significant inhibitory activity with IC_<50>≦50 μg/ml. Through a bioassay guided-fractionation of the methanol extract of the fruit of P. emblica, putranjivain A (1) was isolated as a potent inhibitory substance with IC_<50>=3.9 μM, together with 1,6-di-O-galloyl-β-D-glucose (2), 1-O-galloyl-β-D-glucose (3), kaempferol-3-O-β-D-glucoside (4), quercetin-3-O-β-D-glucoside (5) and digallic acid (6). The inhibitory mode of action by 1,2 and 6 was non-competitive with respect to the substrate but competitive with respect to a template-primer. Furthermore, the stereochemistry of 1 was established in this paper by nuclear magnetic resonance spectroscopy.

  Hiv-1, reverse transcriptase inhibition, Egyptian folk medicine, Phyllanthus emblica, tannins, putranjivain A

  NCBI PubMed ID: 7541317
  Publication DOI: 10.1248/cpb.43.641
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Research Institute for Wakan-Yaku (Traditional Sino-Japanese Medicines), Japan, Faculty of Pharmacy, Cairo University, Egypt
  Methods: 13C NMR, 1H NMR, FAB-MS, TLC, UV, biological assay
  
   
  
  Phyllanthus emblica
  CSDB ID 120585 (all data & tools)

Show legend Show as text

Structure type: monomer
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 8631
  Sordon S, Popłoński J, Huszcza E "Microbial glycosylation of flavonoids" - Polish Journal of Microbiology 65(2) (2016) 137-151
  

  Flavonoids constitute a large group of polyphenolic compounds naturally found in plants, which have a wide range of biological activity. Although flavonoids are beneficial to human health, their application is limited by their low bioavailability and poor water-solubility. Therefore, recently there has been a particular interest in glycosylated forms of flavonoids, which usually are better soluble, more stable, and more functional compared to their aglycones. Microbial transformation of natural flavonoids may be an attractive way of receiving their glycosylated derivatives in amounts sufficient for the research on the effect of glycoside group on compound properties and for further application of these compounds as ingredients of dietary supplements and pharmaceuticals.

  glycosides, biotransformation, microbial glycosylation, flavonoids

  NCBI PubMed ID: 28517915
  Journal NLM ID: 101229003
  Publisher: Polskie Towarzystwo Mikrobiologow
  Correspondence: sandra.sordon@up.wroc.pl
  Institutions: Faculty of Food Science, Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland
  
   
  
  Cunninghamella echinulata CBS 596.68
  CSDB ID 48943 (all data & tools)

Show legend Show as text

Structure type: monomer ; 441.07 [M+Na]+
C₂₀H₁₈O₁₀
Compound class: glycoside
Contained glycoepitopes: IEDB_114701,IEDB_167188,IEDB_174332

• Article ID: 8894
  Saltarelli R, Palma F, Gioacchini AM, Calcabrini C, Mancini U, De Bellis R, Stocchi V, Potenza L "Phytochemical composition, antioxidant and antiproliferative activities and effects on nuclear DNA of ethanolic extract from an Italian mycelial isolate of Ganoderma lucidum" - Journal of Ethnopharmacology 231 (2019) 464-473
  

  Ganoderma lucidum (Curtis) P. Karst. (also known as Linghzhi and Reishi) is the most appreciated and revered medicinal mushroom across many Asian countries, but its properties have also attracted interest in Western countries. Indeed, in the West, it is now commercially available as a dietary supplement in preparations mainly made from spores, fruiting bodies and mycelia. It is employed in both nutraceutical and pharmacological formulations either for its immuno-modulating anti-inflammatory properties or as an effective adjuvant therapy in the treatment of several chronic diseases as well as in cancer treatment. The aim of this investigation was to show the phytochemical composition and antioxidant and antiproliferative activities of an ethanolic extract from an Italian mycelial isolate of Ganoderma lucidum and to assess its effects on nuclear DNA. LC/ESI-MS and tandem mass spectrometry MSMS were used to obtain structural identification of ethanolic G. lucidum extract constituents. Antioxidant activities were determined by the DPPH method, chelating effect on Fe2+ and lipoxygenase inhibition while cytotoxic activities using the MTT assay. Effects on nuclear DNA were evaluated using the DNA nicking assay in a cell-free system and the fast halo assay performed on oxidatively injured human U937 cells; apoptosis induction was investigated using the non-denaturing fast halo assay and DNA laddering detection. This extract was rich in several bioactive compounds, mainly phenolic and triterpenic acids. It showed antioxidant activity and protective effects in oxidatively injured DNA in cell-free analyses and antiproliferative, genotoxic, and proapoptotic effects in the cell model. Italian G. lucidum mycelium isolate appears to be a source of various natural compounds that may have applications as chemopreventive agents or functional foods.

  Ganoderma lucidum, DPPH, DNA damage, fast halo, MTT assay, U937 cells

  NCBI PubMed ID: 30513345
  Publication DOI: 10.1016/j.jep.2018.11.041
  Journal NLM ID: 7903310
  Publisher: Limerick: Elsevier Sequoia
  Correspondence: Saltarelli R ; Palma F ; Gioacchini AM ; Calcabrini C ; Mancini U ; De Bellis R ; Stocchi V ; Potenza L
  Institutions: Department of Biomolecular Sciences, University of Urbino Carlo Bo, Urbino, Italy, Department for Life Quality Studies, Alma Mater Studiorum-University of Bologna, Rimini, Italy
  Methods: DNA techniques, inhibition studies, extraction, cell growth, LC-ESI-MS/MS, enzymatic assay, antioxidant activities, cell viability assay, centrifugation
  
   
  
  Ganoderma lucidum
  CSDB ID 49664 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 637.1758 [M+H]+
C₂₉H₃₂O₁₆
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_190606,IEDB_225177,IEDB_885823,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88

• Article ID: 9103
  Harwoko H, Hartmann R, Daletos G, Ancheeva E, Frank M, Liu Z, Proksch P "Biotransformation of host plant flavonoids by the fungal endophyte Epicoccum nigrum" - Biological Chemistry and Chemical Biology 4(45) (2019) 13054-13057
  

  Fermentation of the fungus Epicoccum nigrum isolated from leaves of Salix sp. on green lentil solid medium yielded the flavonol kaempferol (3) as well as two kaempferol O-diglyco-sides (1 and 2) including the new compound 1. The fungal flavonoids bear strong structural similarities to kaempferol derivatives such as kaempferol O-glycoside (4) being present in green lentils. Furthermore, feeding experiments were conducted by adding flavonoids (kaempferol and rutin) as precursors to solid rice media followed by HPLC and LC-MS analyses. Fermentation of the fungus on flavonoid free solid rice medium afforded flavonoid free extracts indicating that the fungal flavonoids originate through hydrolytic cleavage of kaempferol glycosides such as 4 followed by glycosylation and acetylation. This study suggests that E. nigrum is capable of biotransformation reactions of plant derived flavonoids whereas de novo biosynthesis of flavonoids is less likely.

  Epicoccum nigrum, biotransformation, Salix sp.

  Publication DOI: 10.1002/slct.201903168
  Publisher: Wiley
  Correspondence: Liu Z ; Proksch P
  Institutions: Institute of Pharmaceutical Biology and Biotechnology, Heinrich Heine University, Duesseldorf, Germany, Department of Pharmacy, Faculty of Health Sciences, Universitas Jenderal Soedirman, Purwokerto, Indonesia, Institute of Complex Systems: Strukturbiochemie (ICS-6), Forschungszentrum Jülich, Juelich, Germany
  Methods: 13C NMR, 1H NMR, NMR-2D, UV, biosynthetic methods, extraction, LC-ESI-MS, cell growth, HPLC-DAD
  
   
  
  Epicoccum nigrum
  CSDB ID 50172 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: biorobin
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_190606,IEDB_225177,IEDB_885823,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88

• Article ID: 9103
  Harwoko H, Hartmann R, Daletos G, Ancheeva E, Frank M, Liu Z, Proksch P "Biotransformation of host plant flavonoids by the fungal endophyte Epicoccum nigrum" - Biological Chemistry and Chemical Biology 4(45) (2019) 13054-13057
  

  Fermentation of the fungus Epicoccum nigrum isolated from leaves of Salix sp. on green lentil solid medium yielded the flavonol kaempferol (3) as well as two kaempferol O-diglyco-sides (1 and 2) including the new compound 1. The fungal flavonoids bear strong structural similarities to kaempferol derivatives such as kaempferol O-glycoside (4) being present in green lentils. Furthermore, feeding experiments were conducted by adding flavonoids (kaempferol and rutin) as precursors to solid rice media followed by HPLC and LC-MS analyses. Fermentation of the fungus on flavonoid free solid rice medium afforded flavonoid free extracts indicating that the fungal flavonoids originate through hydrolytic cleavage of kaempferol glycosides such as 4 followed by glycosylation and acetylation. This study suggests that E. nigrum is capable of biotransformation reactions of plant derived flavonoids whereas de novo biosynthesis of flavonoids is less likely.

  Epicoccum nigrum, biotransformation, Salix sp.

  Publication DOI: 10.1002/slct.201903168
  Publisher: Wiley
  Correspondence: Liu Z ; Proksch P
  Institutions: Institute of Pharmaceutical Biology and Biotechnology, Heinrich Heine University, Duesseldorf, Germany, Department of Pharmacy, Faculty of Health Sciences, Universitas Jenderal Soedirman, Purwokerto, Indonesia, Institute of Complex Systems: Strukturbiochemie (ICS-6), Forschungszentrum Jülich, Juelich, Germany
  Methods: 13C NMR, 1H NMR, NMR-2D, UV, biosynthetic methods, extraction, LC-ESI-MS, cell growth, HPLC-DAD
  
   
  
  Epicoccum nigrum
  CSDB ID 50173 (all data & tools)

Show legend Show as text

Structure type: monomer ; 595.1434 [M+H]+
Trivial name: buddlenoid A
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 9193
  Ukaegbu CI, Shah SR, Hamid HA, Alara OR, Sarker MZI "Phenolic compounds of aqueous and methanol extracts of Hypsizygus tessellatus (brown and white var.) and Flammulina velutipes caps: antioxidant and antiproliferative activities" - Pharmaceutical Chemistry Journal 54(2) (2020) 170-183
  

  Since the World Health Organization has suggested the exploration of natural products for cancer management owing to the side effects of chemotherapy and irradiation on humans and breast cancer accounts for the highest number of cancer related deaths globally, this study has examined antiproliferative effects of the aqueous and methanol extracts of Hypsizygus tessellatus (brown and white var.) and Flammulina velutipes caps against two breast cancer cell lines. The antioxidant and antiproliferative activities of these mushroom extracts were evaluated in vitro using chemical-based (for antioxidant activity) and cell (for antiproliferative activity) approaches. Furthermore, the phytochemical composition of the mushroom extracts were identified using mass spectroscopy (UPLC-QTOF/MS). The obtained results showed aqueous extracts of F. velutipes (Enoki) and white H. tessellatus (Bunapi shimeji) caps to possess higher antiodixant activities against DPPH (IC50 = 0.202 and 0.573 mg/mL, respectively), and H2O2 (IC50 = 0.622 and 0.745 mg/mL, respectively) compared tothe methanol extracts. Aqueous extracts of the mushrooms also showed better ferric reducing antioxidant power (FRAP) values against ferric ions compared to the methanol extracts. Finally, the mushroom extracts showed good antiproliferative activities against human breast cancer cell lines. These findings suggest the presence of phytochemicals with antiproliferative and antioxidant acrtivities in the mushroom extracts studied.

  Antioxidant, antiproliferative, phytochemicals, H. tessellatus, F. velutipes

  Publication DOI: 10.1007/s11094-020-02174-2
  Journal NLM ID: 0323156
  Publisher: New York: Springer US
  Correspondence: Ukaegbu CI
  Institutions: Faculty of Industrial Sciences &Technology, Universiti Malaysia Pahang, Gambang, Malaysia, Faculty of Chemical and Natural Resources Engineering, Universiti Malaysia Pahang, Gambang, Malaysia, Faculty of Pharmacy, International Islamic University, Malaysia
  Methods: extraction, calorimetry, antioxidant activities, cell viability assay, evaporation, MTT, filtration, Folin phenol reagent method, UPLC-QTOF-MS, Shinoda test, ferric chloride test, Mayer test, Salkowski test, foam test
  
   
  
  Flammulina velutipes
  CSDB ID 50478 (all data & tools)

Show legend Show as text

Structure type: monomer ; 593 [M-H]-
C₃₀H₂₆O₁₃
Trivial name: buddlenoid A
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 9198
  Kubo I, Yokokawa Y "Two tyrosinase inhibiting flavonol glycosides from Buddleia coriacea" - Phytochemistry 31(3) (1992) 1075-1077
  

  Two new flavonol glycosides, buddlenoids A and B, have been isolated and identified as tyrosinase inhibitors from the aerial parts of Buddleia coriacea. Their structures were deduced from spectroscopic evidence to be kaempferol 7-(6″-p-coumaroylglucoside) and isorhamnetin 7-(6″-p-coumaroylglucoside). Both buddlenoids showed high inhibition of mushroom tyrosinase.

  Buddleia coriacea, Loganiaceae, flavonol glucoside, buddlenoid A, buddlenoid B, tyrosinase inhibitory activity

  Publication DOI: 10.1016/0031-9422(92)80084-R
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Division of Entomology and Parasitology, College of Natural Resources, University of California, Berkeley, USA
  Methods: 13C NMR, 1H NMR, FAB-MS, inhibition studies, extraction, CC, melting point determination, enzymatic assay
  
   
  
  Buddleja coriacea
  CSDB ID 50499 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: buddlenoid A
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 9199
  Kubo I, Yokokawa Y, Kinst-Hori I "Tyrosinase inhibitors from Bolivian medicinal plants" - Journal of Natural Products 58(5) (1995) 739-743
  

  Bioassay-guided fractionation monitored by mushroom tyrosinase (EC 1.14.18.1) activity, afforded six inhibitors from three Bolivian medicinal plants, Buddleia coriacea, Gnaphalium cheiranthifolium, and Scheelea princeps. These inhibitors, which are all known phenolic compounds, inhibited the oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA) mediated by a mushroom tyrosinase.

  Buddleia coriacea, Loganiaceae, flavonol glucoside, buddlenoid A, buddlenoid B, tyrosinase inhibitory activity

  NCBI PubMed ID: 7623048
  Publication DOI: 10.1021/np50119a013
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Institutions: Division of Entomology and Parasitology, College of Natural Resources, University of California, Berkeley, USA
  Methods: 13C NMR, 1H NMR, FAB-MS, inhibition studies, HPLC, extraction, CC, reversed-phase chromatography, enzymatic assay
  
   
  
  Buddleja coriacea
  CSDB ID 50501 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: tiliroside
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 9205
  Nshimo CM, Pezzuto JM, Kinghorn AD, Farnsworth NR "Cytotoxic constituents of Muntingia calabura leaves and stems collected in Thailand" - International Journal of Pharmacognosy 31(1) (1993) 77-81
  

  From samples of Muntingia calabura leaves and stems of Thai origin were obtained the cytotoxic flavonoids chrysin, 2′, 4′-dihydroxychalcone, and galangin 3,7-dimethyl ether. These compounds were active against one or more of a panel of human and murine cell lines. Also isolated were the inactive compounds, 5,7-dihydroxy-8-methoxyflavonol, tiliroside and buddlenoid A.

  cytotoxicity, Muntingia calabura, flavonoid glycoside

  Publication DOI: 10.3109/13880209309082922
  Journal NLM ID: 9107512
  Publisher: Lisse: Swets & Zeitlinger
  Institutions: Program for Collaborative Research in the Pharmaceutical Sciences Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA
  Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, IR, TLC, UV, extraction, optical rotation measurement, CI-MS, CC, melting point determination, cytotoxicity assay, recrystallization
  
   
  
  Muntingia calabura
  CSDB ID 50535 (all data & tools)

Show legend Show as text

Structure type: monomer ; 595 [M+H]+
Trivial name: buddlenoid A
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 9205
  Nshimo CM, Pezzuto JM, Kinghorn AD, Farnsworth NR "Cytotoxic constituents of Muntingia calabura leaves and stems collected in Thailand" - International Journal of Pharmacognosy 31(1) (1993) 77-81
  

  From samples of Muntingia calabura leaves and stems of Thai origin were obtained the cytotoxic flavonoids chrysin, 2′, 4′-dihydroxychalcone, and galangin 3,7-dimethyl ether. These compounds were active against one or more of a panel of human and murine cell lines. Also isolated were the inactive compounds, 5,7-dihydroxy-8-methoxyflavonol, tiliroside and buddlenoid A.

  cytotoxicity, Muntingia calabura, flavonoid glycoside

  Publication DOI: 10.3109/13880209309082922
  Journal NLM ID: 9107512
  Publisher: Lisse: Swets & Zeitlinger
  Institutions: Program for Collaborative Research in the Pharmaceutical Sciences Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA
  Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, IR, TLC, UV, extraction, optical rotation measurement, CI-MS, CC, melting point determination, cytotoxicity assay, recrystallization
  
   
  
  Muntingia calabura
  CSDB ID 50536 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: robinin
Compound class: saponin glycoside, glycoside, flavonoid glycoside, flavonol glycoside, flavone glycoside
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_190606,IEDB_225177,IEDB_885823,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88

• Article ID: 10000
  Kang SS, Lee YS, Lee EB "Saponins and flavonoid glycosides from yellow sweetclover" - Archives of Pharmacal Research 11 (1988) 197-202
  

  A new saponin, 3-O-[a-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl(1→2)-β-D-glucuronopyranosyl]soyasapogenol B carboxylate (6) has been isolated from the medicinal plant yellow sweetclover together with azukisaponin II(7), robinin(8), and clovin(9). 7, 8, and 9 are reported for the first time from this plant. The new saponin(6) exhibited inhibitory action on leucocyte migration in inflammation.

  flavonoid glycoside, saponin, Leguminosae, yellow sweetclover, azukisaponin V carboxylate, azukisaponin II, robinin, clovin, leucocyte migration inhibitor

  Publication DOI: 10.1007/BF02861309
  Journal NLM ID: 8000036
  Publisher: Pharmaceutical Society of Korea
  Institutions: Natural Products Research Institute, Seoul National University, Seoul, South Korea
  Methods: 13C NMR, 1H NMR, partial acid hydrolysis, acid hydrolysis, methylation analysis, inhibitory action assay
  
   
  
  Melilotus officinalis
  CSDB ID 205104 (all data & tools)
• Article ID: 10632
  Markham KR, Ofman DJ "Lisianthus flavonoid pigments and factors influencing their expression in flower colour" - Phytochemistry 34 (1993) 679-685
  

  NMR, MS and analytical data are cited in support of the newly defined complete structures of the major flavonoid pigments and copigments in lisianthus flowers. The copigments newly characterized and found in flowers of all colours are kaempferol-3-O-β-D-[6-O-rhamnopyranosyl-4-O-E-p-coumaroylgalactopyranoside]-7-O-α-L-rhamnopyranoside, its Z-isomer and by analogy, the lesser isorhamnetin and myricetin equivalents. Purple flower pigments with newly defined structures are: delphinidin-3-O-β-D-[6-O-α-L-rhamnopyranosylgalactopyranoside] 5-O-β-D-[6-E-p-coumaroylglucopyranoside], its Z-isomer, and by analogy the lesser cyanidin equivalent, together with delphinidin-3-O-β-D-galactopyranoside-5-O-β-D-[6-E-p-coumaroylglucopyranoside], its Z-isomer, and by analogy the lesser cyanidin equivalent. Different pigment/copigment compositions are shown to account for the basic colour differences between white, cream, pink, mauve and purple flowers, but other factors involved in stabilizing and fine-tuning the colours are pigment concentration, copigmentation and pH control.

  pH, anthocyanins, flavonol glycosides, Eustoma grandiflorum, Gentianaceae, lisianthus, copigmentation, colour

  NCBI PubMed ID: 7764146
  Publication DOI: 10.1016/0031-9422(93)85339-S
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Industrial Research Ltd., Lower Hutt, New Zealand
  Methods: 13C NMR, 1H NMR, FAB-MS, HPLC, PC
  
   
  
  Eustoma grandiflorum
  CSDB ID 146056 (all data & tools)
• Article ID: 11821
  Rastrelli L, Caceres A, De Simone F, Aquino R "Studies on the constituents of Gliricidia sepium (Leguminosae) leaves and roots: isolation and structure elucidation of new triterpenoid saponins and aromatic compounds" - Journal of Agricultural and Food Chemistry 47(4) (1999) 1537-1540
  

  Our research program on the Central American fooder plant Gliricidia sepium led to the discovery of two new triterpene saponins (1 and 2) and known aromatic compounds. The new compounds possess 3β,21β,24-trihydroxy-22-oxoolean-12-ene as an aglycon. The oligosaccharide moiety linked to C-3 of the aglycon contained two pyranoses (glucuronic acid and xylose); in addition the glucose residue of both 1 and 2 is also linked to C-21. Structure elucidation of these new compounds through the extensive use of 1D and 2D NMR techniques have provided detailed information about the sapogenin and the saccharide chains, inclusive of sugar sequence and the position of glycosylation.

  root, leaves, flavonol glycosides, Leguminosae, triterpenoid saponins, Gliricidia sepium, fooder source, 13C NMR analysis

  NCBI PubMed ID: 10564013
  Publication DOI: 10.1021/jf9808731
  Journal NLM ID: 0374755
  Publisher: American Chemical Society
  Correspondence: Rastrelli L
  Institutions: Dipartimento di Scienze Farmaceutiche, Facoltà di Farmacia, Università di Salerno, Piazza V. Emanuele 9, 84084 Penta di Fisciano (SA), Italy, Departamento de Citohistología, Escuela de Quimíca Biologica, Universidad de San Carlos de Guatemala, Zona 12, 01002 Guatemala
  Methods: 13C NMR, 1H NMR, FAB-MS, TLC, optical rotation measurement, ROESY, TOCSY, RP-HPLC, HMBC, HSQC, DFQ-COSY
  
   
  
  Gliricidia sepium
  CSDB ID 63121 (all data & tools)
• Article ID: 12447
  Markham KR, Ryan KG, Gould KS, Rickards GK "Cell wall sited flavonoids in lisianthus flower petals" - Phytochemistry 54(7) (2000) 681-687
  

  Flavonoids are considered to be located predominantly in the vacuoles of epidermal cells and in the cuticular wax of terrestrial plants. However, recent reports have suggested that flavonoids may also reside elsewhere in the cells of green leaves. In the present study of lisianthus flower petals, it is demonstrated that ca. 30% of the whole petal flavonol glycosides are located in the cell wall. These flavonol glycosides are distinguished from the vacuolar glycosides in that they lack acylation. Evidence from light and confocal microscopy studies is corroborated by HPLC analyses of isolated protoplasts and cell wall digests, these having been produced by enzymic treatment of epidermal peels. This is the first report of the occurrence of flavonoids in petal cell walls, and it describes novel methodology for such studies.

  Eustoma grandiflorum; lisianthus; petals; cell wall flavonoids; CLSM; HPLC

  NCBI PubMed ID: 10975502
  Publication DOI: 10.1016/s0031-9422(00)00180-1
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: k.markham@irl.cri.nz
  Institutions: NZ Institute of Industrial Research and Development, Lower Hutt, New Zealand, School of Biological Sciences, University of Auckland, Auckland, New Zealand, School of Biological Sciences, Victoria University of Wellington, Wellington, New Zealand
  Methods: HPLC, UV, extraction, microscopy
  
   
  
  Eustoma grandiflorum
  CSDB ID 66725 (all data & tools)
• Article ID: 12511
  Murakami T, Kohno K, Kishi A, Matsuda H, Yoshikawa M "Medicinal foodstuffs. XIX. Absolute stereostructures of canavalioside, a new ent-kaurane-type diterpene glycoside, and gladiatosides A1, A2, A3, B1, B2, B3, C1 and C2, new acylated flavonol glycosides, from sword bean, the seeds of Canavalia gladiata" - Chemical and Pharmaceutical Bulletin 48(11) (2000) 1673-1680
  

  A new ent-kaurane-type glycoside, canavalioside, and eight new acylated flavonol glycosides, gladiatosides A1, A2, A3, B1, B2, B3, C1 and C2, were isolated from the seed of Canavalia gladiata together with robinin, kaempferol 3-O-β-D-galactopyranosyl-7-O-α-L-rhamnopyranoside, and kaikasaponin III. The absolute stereostructures of canavalioside and gladiatosides A1, A2, A3, B1, B2, B3, C1 and C2 were elucidated on the basis of chemical and physicochemical evidence.

  acylated flavonol glycoside, canavalioside, gladiatoside, Canavalia gladiata, ent-kaurane-type diterpene, sword bean

  NCBI PubMed ID: 11086895
  Publication DOI: 10.1248/cpb.48.1673
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Correspondence: Yoshikawa M
  Institutions: Kyoto Pharmaceutical University, Kyoto, Japan
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, HPLC, extraction, HR-ESI-MS, evaporation, centrifugation
  
   
  
  Canavalia gladiata
  CSDB ID 66991 (all data & tools)
• Article ID: 12844
  Yahara S, Kohjyouma M, Kohoda H "Flavonoid glycosides and saponins from Astragalus shikokianus" - Phytochemistry 53(4) (2000) 469-471
  

  A new flavonol glycoside, kaempferol 3-O-α-L-rhamnopyranosy1-(1 → 6)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-galactopyranosyl-7-O-α-L-rhamnopyranoside, named astrasikokioside I, was isolated from aerial part of Astragalus shikokianus, together with two flavonol glycosides, kaempferol 3-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-galactopyranosyl-7-O-α-L-rhamnopyranoside, robinin, and three triterpenoid glycosides, soyasaponin I, sophoraflavoside II and robinioside E.

  triterpenoid glycoside, flavonol glycoside, Leguminosae, robinin, clovin, soyasaponin I, sophoraflavoside, Astragalus shikokianus, astrasikokioside I, robinioside E

  NCBI PubMed ID: 10731025
  Publication DOI: 10.1016/s0031-9422(99)00512-9
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: yaharas1@gpo.kumamoto-u.ac.jp
  Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, Kumamoto, Japan, Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima, Japan
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, enzymatic hydrolysis, acid hydrolysis, HPLC, optical rotation measurement, HR-FAB-MS
  
   
  
  Astragalus sikokianus
  CSDB ID 68677 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: astragalin
Compound class: glycoside, flavonoid glycoside, flavonol glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 10024
  Yoshikawa M, Shimada H, Saka M, Yoshizumi S, Yamahara J, Matsuda H "Medicinal foodstuffs. V. Moroheiya. (1): Absolute stereostructures of Corchoionosides A, B, and C, histamine release inhibitors from the leaves of Vietnamese Corchorus olitorius L. (Tiliaceae)" - Chemical and Pharmaceutical Bulletin 45 (1997) 464-469
  

  Three new ionone glucosides named corchoionosides A, B, and C were isolated from the leaves of Corhorus olitorius, commonly called "moroheiya" in Japanese, together with seven known compounds, an ionone glucoside (6S, 9R)-roseoside, a monoterpene glucoside betulalbuside A, two flavonol glucosides astragalin and isoquercitrin, two coumarin glucosides scopolin and cichoriine, and chlorogenic acid. The absolute stereostructures of corchoionosides A, B, and C were determined by chemical and physicochemical evidence, which included the result of application of a modified Mosher's method, the CD helicity rule, and chemical correlation with (6S, 9R)-roseoside. Corchoionosides A and B and (6S, 9R)-roseoside were found to inhibit the histamine release from rat peritoneal exudate cells induced by antigen-antibody reaction.

  histamine release inhibitor, corchoionoside, Corchorus olitorius, ionone glucoside, (6S, 9R)-roseoside, moroheiya

  NCBI PubMed ID: 9085554
  Publication DOI: 10.1248/cpb.45.464
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Kyoto Pharmaceutical University, Kyoto, Japan
  Methods: 13C NMR, 1H NMR, gel filtration, FAB-MS, TLC, HPLC, UV, enzymatic digestion, CD, NaBH4 reduction, bioassay, acetylation analysis
  
   
  
  Corchorus olitorius
  CSDB ID 270774 (all data & tools)
• Article ID: 10524
  Cardenas LC, Rodriquez J, Villaverde MC, Riguera R, Cadena R, Otero JA "The analgesic activity of Hedyosmum bonplandianum: Flavonoid glycosides" - Planta Medica 59 (1993) 26-27
  

  Kaempferol 3-O-[α-L-rhamnopyranosyl(1→6)-β-D-glucopyranoside] and kaempferol 3-O-[β-D-glucopyranoside] were isolated from the leaves of Hedyosmum bonplandianum H.B.K. (Chloranthaceae), which is used in Colombian folk medicine as an analgesic. The n-butanol extract and the glycosyl flavonoids isolated exhibited significant analgesic activity in mice.

  NCBI PubMed ID: 8441777
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Institutions: Departamento de Química, Orgánica, Facultad de Química, Universidad de Santiago de Compostela, Spain
  
   
  
  Hedyosmum bonplandianum
  CSDB ID 147282 (all data & tools)
• Article ID: 10620
  Tanaka N, Yuhara H, Wada H, Murakami T, Cambie RC, Braggins JE "Phenolic consituents of Pteridium esculentum" - Phytochemistry 32 (1993) 1037-1039
  

  Two new compounds, (5S,6S,9S,lOS)-lS-hydroxycadina-3,11-dien-2-one and p-hydroxystyrene β-vicianoside, together with p-hydroxystyrene b-D-glucoside, kaempferol 3-O-b-D-glucoside, kaempferol 3-O-(2-0-b-D-xylosyl)-b-D-glucoside, kaempferol 3-0-(6-p-coumaroyl)-b-D-glucoside and chlorogenic acid, were isolated from the fronds of Pteridium esculentum. Their structures were elucidated from spectroscopic data.

  flavonoid, fern, Pteridium esculentum, Pteridaceae, bracken, cadinane, p-hydroxystyrene glycoside

  Publication DOI: 10.1016/0031-9422(93)85251-L
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Faculty of Pharmaceutical Sciences, Science University of Tokyo, Funakawaramachi, Ichigaya, Shinjuku-ku, Tokyo, Japan, Faculty of Industrial Sciences and Technology, Science University of Tokyo, Yamasaki, Noda, Chiba, Japan, Department of Botany, University of Auckland Private Bag, Auckland, New Zealand
  Methods: 13C NMR, 1H NMR, EI-MS, gel filtration, IR, acid hydrolysis, UV, HR-MS
  
   
  
  Pteridium esculentum
  CSDB ID 245850 (all data & tools)
• Article ID: 11226
  Yin R, Han K, Heller W, Albert A, Dobrev PI, Zažímalová E, Schäffner AR "Kaempferol 3-O-rhamnoside-7-O-rhamnoside is an endogenous flavonol inhibitor of polar auxin transport in Arabidopsis shoots" - New Phytologist 201 (2013) 466-475
  

  Polar auxin transport (PAT) plays key roles in the regulation of plant growth and development. Flavonoids have been implicated in the inhibition of PAT. However, the active flavonoid derivative(s) involved in this process in vivo has not yet been identified. Here, we provide evidence that a specific flavonol bis-glycoside is correlated with shorter plant stature and reduced PAT. Specific flavonoid-biosynthetic or flavonoid-glycosylating steps were genetically blocked in Arabidopsis thaliana. The differential flavonol patterns established were analyzed by high-performance liquid chromatography (HPLC) and related to altered plant stature. PAT was monitored in stem segments using a radioactive [3H]-indole-3-acetic acid tracer. The flavonoid 3-O-glucosyltransferase mutant ugt78d2 exhibited a dwarf stature in addition to its altered flavonol glycoside pattern. This was accompanied by reduced PAT in ugt78d2 shoots. The ugt78d2-dependent growth defects were flavonoid dependent, as they were rescued by genetic blocking of flavonoid biosynthesis. Phenotypic and metabolic analyses of a series of mutants defective at various steps of flavonoid formation narrowed down the potentially active moiety to kaempferol 3-O-rhamnoside-7-O-rhamnoside. Moreover, the level of this compound was negatively correlated with basipetal auxin transport. These results indicate that kaempferol 3-O-rhamnoside-7-O-rhamnoside acts as an endogenous PAT inhibitor in Arabidopsis shoots.

  Arabidopsis thaliana, flavonol glycoside, flavonol biosynthesis, flavonol glycosyltransferases, plant growth, polar auxin transport

  Publication DOI: 10.1111/nph.12558
  Journal NLM ID: 9882884
  Publisher: Blackwell Publishing
  Correspondence: schaeffner@helmholtz-muenchen.de
  Institutions: Institute of Biochemical Plant Pathology, Helmholtz Zentrum München, Neuherberg, Germany, Research Unit Environmental Simulation, Helmholtz Zentrum München, Neuherberg, Germany, Institute of Experimental Botany, Academy of Sciences of the Czech Republic, Prague 6, Czech Republic, Department of Botany and Plant Biology, University of Geneva, Sciences III, Geneva 4, Switzerland
  Methods: biological assays, HPLC, LC-MS, genetic manipulations
  
   
  
  Arabidopsis thaliana
  CSDB ID 60897 (all data & tools)
• Article ID: 11688
  Yu SC, Wu QL, Wang LW, Yang JS, Xiao PG "Flavonoid glycosides from Thalictrum przewalskii" - Journal of Asian Natural Products Research 1(4) (1999) 301-306
  

  A new flavonoid glycosides, 5,7-dihydroxy-4'-methoxyflavone-7-O-[6-O-(4-O-acetyl-α-L-rhamnosyl)-3-O-β-D-glucosyl]-6-O-acetyl-β-D-glucoside and three known flavonoid glycosides, 5,7-dihydroxy-4'-methoxyflavone-7-O-[6-O-(4-O-acetyl-α-L-rhamnosyl)]-β-D-glucoside, 3,5,7,4'-tetrahydroxyflavonol-3-O-β-D-glucoside and 5,7-dihydroxy-4'-methoxyflavone-7-O-(6-O-α-L-rhamnosyl)-β-D-glucoside were isolated from the whole plant of Thalictrum przewalskii. Their structures were determined on the basis of spectroscopic evidences.

  5, flavonoid glycoside, Thalictrum, Thalictrum przewalskii, 7-dihydroxy-4′-methoxyflavone-7-O-[6-O-(4-O-acetyl-α-L-rhamnosyl)-3-O-β-D-glucosyl]-6-O-acetyl-β-D-glucoside

  NCBI PubMed ID: 11523550
  Publication DOI: 10.1080/10286029908039878
  Journal NLM ID: 100888334
  Publisher: Harwood Academic Publishers; London: Informa Healthcare
  Correspondence: Yu SC
  Institutions: Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Dongbei Wang Haidian District, Beijing, 100094, China
  Methods: 13C NMR, 1H NMR, EI-MS, IR, UV, HMBC, MALDI-TOF HRMS
  
   
  
  Thalictrum przewalskii
  CSDB ID 62517 (all data & tools)
• Article ID: 12654
  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: 11130666
  Publication DOI: 10.1016/s0031-9422(00)00227-2
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: dyacsan@ib.usp.br
  Institutions: Institute of Biosciences, University of São Paulo, São Paulo, Brazil
  
   
  
  Annonaceae
  CSDB ID 67697 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 755.2345 [M+H]+
C₃₄H₄₃O₁₉
Compound class: flavonol glycoside
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_190606,IEDB_225177,IEDB_885823,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88

• Article ID: 10499
  Satake T, Hori K, Kamiya K, Saiki Y, Fujimoto Y, Kimura Y, Maksut C, Mekin T "Studies on the constituents of Turkish plants. I. Flavonol triglycosides from the fruit of Rhamnus thymifolius" - Chemical and Pharmaceutical Bulletin 41(10) (1993) 1743-1745
  

  Two new flavonol glycosides have been isolated from the fruit of Turkish Rhamnus thymifolius (Rhamnaceae) and their structures were elucidated as kaempferol-3-O-α-L-rhamnopyranosyl(1→3)-(4-O-acetyl)-O-α-L-rhamnopyranosyl-(1→6)-O-β-D-galactopyranoside and kaempferol-4'-O-α-L-rhamnopyranosyl(1→3)-O-α-L-rhamnopyranosyl(1→6)-O-β-D-galactopyranoside based on spectral and chemical evidence.

  Rhamnaceae, Rhamnus thymifolius, kaempferol triglycoside, Turkish plant

  Publication DOI: 10.1248/cpb.41.1743
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Department of. Pharmaceutical Sciences, Kobe Gakuin University, Japan, College of Pharmacy, Nihon University, Japan, Faculty of Pharmacy, Ankara University, Turkey
  Methods: 13C NMR, 1H NMR, IR, acid hydrolysis, alkaline hydrolysis, SI-MS
  
   
  
  Rhamnus thymifolius
  CSDB ID 120239 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 783.2359 [M+H]+
C₃₅H₄₃O₂₀
Compound class: flavonol glycoside
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_190606,IEDB_225177,IEDB_885823,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88

• Article ID: 10499
  Satake T, Hori K, Kamiya K, Saiki Y, Fujimoto Y, Kimura Y, Maksut C, Mekin T "Studies on the constituents of Turkish plants. I. Flavonol triglycosides from the fruit of Rhamnus thymifolius" - Chemical and Pharmaceutical Bulletin 41(10) (1993) 1743-1745
  

  Two new flavonol glycosides have been isolated from the fruit of Turkish Rhamnus thymifolius (Rhamnaceae) and their structures were elucidated as kaempferol-3-O-α-L-rhamnopyranosyl(1→3)-(4-O-acetyl)-O-α-L-rhamnopyranosyl-(1→6)-O-β-D-galactopyranoside and kaempferol-4'-O-α-L-rhamnopyranosyl(1→3)-O-α-L-rhamnopyranosyl(1→6)-O-β-D-galactopyranoside based on spectral and chemical evidence.

  Rhamnaceae, Rhamnus thymifolius, kaempferol triglycoside, Turkish plant

  Publication DOI: 10.1248/cpb.41.1743
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Department of. Pharmaceutical Sciences, Kobe Gakuin University, Japan, College of Pharmacy, Nihon University, Japan, Faculty of Pharmacy, Ankara University, Turkey
  Methods: 13C NMR, 1H NMR, IR, acid hydrolysis, alkaline hydrolysis, SI-MS
  
   
  
  Rhamnus thymifolius
  CSDB ID 120240 (all data & tools)