Show legend Show as text

Structure type: monomer
Trivial name: vitexin
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_613414,IEDB_983931,SB_192

• Article ID: 6181
  Hussain H, Mamadalieva NZ, Ali I, Elizbit, Green IR, Wang D, Zou L, Simal-Gandara J, Cao H, Xiao J "Fungal glycosides: Structure and biological function" - Trends in Food Science and Technology 110 (2021) 611-651
  

  Background: Natural products acquire vast and intriguing structural diversity and have been recognized as a tremendously diverse source of new lead compounds. Numerous bioactive secondary metabolites are present in the form of glycosylated molecules in which the sugar parts are normally associated with the interaction along with molecular recognition of the cellular target. Scope and approach: The presence of sugar entities are crucial as well as in some cases necessary, for therapeutic effects. Establishing novel and potent glycosylated secondary metabolites has formed a main goal in the natural product field from fungi and bacteria. These compounds possess a diverse range of sugar units. Key findings and conclusions: Fungi is considered one of the important sources for approved drugs with a diverse range of mode of action. The sugar part in numerous pharmacologically active natural products enhances bioavailability, biological potential, reduce toxicity, and improve stability. The vast majority of glyocosides showed antimicrobial effects, cytotoxic, antiviral and antiinflammatory effects. Notably, numerous fungal glycosides presented in this review illustrate significant antimicrobial effects towards various microorganisms especially against plant pathogens. The antimicrobial effects of these fungal glycosides indicate that these metabolites could be employed as natural preservatives in food in order to abolish or control the growth of pathogenic and spoilage microorganisms.

  glycoside, antimicrobial, fungi, food preservative, secondary metabolites

  Publication DOI: 10.1016/j.tifs.2021.02.029
  Journal NLM ID: 9426004
  Publisher: Cambridge, UK: Elsevier Trends Journals
  Correspondence: Hussain H ; Hussain H ; Xiao J ; Xiao J
  Institutions: Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Halle (Saale), Germany, Institute of the Chemistry of Plant Substances of the Academy Sciences of Uzbekistan, Tashkent, Uzbekistan, School of Pharmaceutical Sciences and Key Laboratory for Applied Technology of Sophisticated Analytical Instruments of Shandong Province, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan, China, Department Materials Engineering, National University of Sciences and Technology (NUST) H12, Islamabad, Pakistan, Department of Chemistry and Polymer Science, University of Stellenbosch, Matieland, South Africa, Key Laboratory of Coarse Cereal Processing, Ministry of Agriculture and Rural Affairs, Chengdu University, Chengdu, China, Nutrition and Bromatology Group, Department of Analytical Chemistry and Food Science, Faculty of Food Science and Technology, University of Vigo - Ourense Campus, Ourense, Spain
  
   
  
  Colletotrichum
  CSDB ID 51544 (all data & tools)
• Article ID: 8166
  Zhou SL, Wang MX, Chen SL "Two compounds from the endophytic Colletotrichum sp. of Ginkgo biloba" - Natural Product Communications 6(8) (2011) 1131-1132
  

  Two compounds, apigenin-8-C-β-D-glucopyranoside and 2-(hydroxymethylthio)ethanol, were extracted from the fermentation products of a strain of endophytic fungus, Colletotrichum sp. NTB-2, isolated from the leafstalk of Ginkgo biloba. The structures of the two compounds were determined on the basis of extensive spectroscopic analysis, including 1D and 2D NMR spectral data. The compounds were obtained from microorganisms for the first time

  endophytic fungi, Ginkgo biloba, Colletotrichum, apigenin-8-C-β-D-glucopyranoside, 2-(hydroxymethylthio)ethanol

  NCBI PubMed ID: 21922917
  Journal NLM ID: 101477873
  Publisher: Natural Product Communications
  Correspondence: chenshuanglin@njnu.edu.cn
  Institutions: College of Life Science, Nanjing Normal University, Nanjing, China
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, extraction, elemental analysis, column chromatography, cell growth, melting point determination
  
   
  
  Colletotrichum sp. NTB-2
  CSDB ID 48079 (all data & tools)

Show legend Show as text

Structure type: monomer ; 415.10 [M+H-H2O]+
C₂₁H₂₀O₁₀
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_613414,IEDB_983931,SB_192

• Article ID: 8716
  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 49661 (all data & tools)

Show legend Show as text

Structure type: monomer ; 417.11 [M+H]+
C₂₁H₂₀O₉
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_225177,IEDB_613414,IEDB_885823

• Article ID: 8716
  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 49662 (all data & tools)

Show legend Show as text

Structure type: monomer ; 485.04 [M+K]+
C₂₁H₁₈O₁₁
Compound class: glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_423153,IEDB_613414

• Article ID: 8716
  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 49665 (all data & tools)

Show legend Show as text

Structure type: monomer ; 445.1138 [M-H]-
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_613414,IEDB_983931,SB_192

• Article ID: 8720
  Sordon S, Popłoński J, Tronina T, Huszcza E "Regioselective O-glycosylation of flavonoids by fungi Beauveria bassiana, Absidia coerulea and Absidia glauca" - Bioorganic Chemistry 93 (2019) ID 102750
  

  In the present study, the species: Beauveria bassiana, Absidia coerulea and Absidia glauca were used in biotransformation of flavones (chrysin, apigenin, luteolin, diosmetin) and flavanones (pinocembrin, naringenin, eriodictyol, hesperetin). The Beauveria bassiana AM 278 strain catalyzed the methylglucose attachment reactions to the flavonoid molecule at positions C7 and C3'. The application of the Absidia genus (A. coerulea AM 93, A. glauca AM 177) as the biocatalyst resulted in the formation of glucosides with a sugar molecule present at C7 and C3' positions of flavonoids skeleton. Nine of obtained products have not been previously reported in the literature.

  biotransformation, Beauveria bassiana, Absidia coerulea, microbial glycosylation, Absidia glauca, flavanones, flavones

  NCBI PubMed ID: 30755333
  Publication DOI: 10.1016/j.bioorg.2019.01.046
  Journal NLM ID: 1303703
  Publisher: Orlando, FL: Academic Press
  Correspondence: Sordon S ; Popłoński J ; Tronina T ; Huszcza E
  Institutions: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, biosynthetic methods, extraction, cell growth, HR-ESI-MS
  
   
  
  Beauveria bassiana AM 278
  CSDB ID 49675 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: cosmosiin, apigenin 7-O-glucoside, rhoifolin, apigenin 7-glucoside, apigetrin
Compound class: glycoside, flavonoid glycoside, flavonol glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_613414,IEDB_983931,SB_192

• Article ID: 8720
  Sordon S, Popłoński J, Tronina T, Huszcza E "Regioselective O-glycosylation of flavonoids by fungi Beauveria bassiana, Absidia coerulea and Absidia glauca" - Bioorganic Chemistry 93 (2019) ID 102750
  

  In the present study, the species: Beauveria bassiana, Absidia coerulea and Absidia glauca were used in biotransformation of flavones (chrysin, apigenin, luteolin, diosmetin) and flavanones (pinocembrin, naringenin, eriodictyol, hesperetin). The Beauveria bassiana AM 278 strain catalyzed the methylglucose attachment reactions to the flavonoid molecule at positions C7 and C3'. The application of the Absidia genus (A. coerulea AM 93, A. glauca AM 177) as the biocatalyst resulted in the formation of glucosides with a sugar molecule present at C7 and C3' positions of flavonoids skeleton. Nine of obtained products have not been previously reported in the literature.

  biotransformation, Beauveria bassiana, Absidia coerulea, microbial glycosylation, Absidia glauca, flavanones, flavones

  NCBI PubMed ID: 30755333
  Publication DOI: 10.1016/j.bioorg.2019.01.046
  Journal NLM ID: 1303703
  Publisher: Orlando, FL: Academic Press
  Correspondence: Sordon S ; Popłoński J ; Tronina T ; Huszcza E
  Institutions: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, biosynthetic methods, extraction, cell growth, HR-ESI-MS
  
   
  
  Absidia caerulea AM 93, Absidia glauca AM 177
  CSDB ID 49687 (all data & tools)
• Article ID: 10438
  Ofman DJ, Markham KR, Vilain C, Molloy BPJ "Flavonoid profiles of New Zealand kauri and other species of Agathis" - Phytochemistry 38 (1995) 1223-1228
  

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

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

  Publication DOI: 10.1016/0031-9422(94)00783-P
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: New Zealand Institute for Industrial Research and Development, Lower Hutt, New Zealand, Manaaki Whenua-Landcare Research, Lincoln, New Zealand
  Methods: 13C NMR, 1H NMR, TLC, LSI-MS, UV, 2D-PC
  
   
  
  Agathis australis
  CSDB ID 146675 (all data & tools)
• Article ID: 10666
  Ohe C, Sugino M, Minami M, Hasegawa C, Ashida K, Ogaki K, Kanamori H "Studies on the cultivation and evaluation of chamomilae flos. Seasonal variation in production of the head (capitula) and accumulation of glycosides in the capitula of Matricaria chamomilla L" - Yakugaku Zasshi = Journal of the Pharmaceutical Society of Japan [Japanese] 115 (1995) 130-135
  
  Journal NLM ID: 0413613
  Publisher: Tokyo: Nihon Yakugakkai
  
   
  
  Matricaria chamomilla
  CSDB ID 149840 (all data & tools)
• Article ID: 11289
  Barakat HH "Chemical investigation of the constitutive phenolics of Ailanthus altissima; The structure of a new flavone glycoside gallate" - Natural Product Sciences 4(3) (1998) 153-157
  

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

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

  Journal NLM ID: 9714997
  Publisher: Seoul, Korea: Korean Society of Pharmacognosy
  Institutions: National Research Centre, Dokki, Cairo, Egypt
  Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, UV, extraction, column chromatography
  
   
  
  Ailanthus altissima
  CSDB ID 63751 (all data & tools)
• Article ID: 11374
  Kumar JK, Rao MS, Rao PS, Toth G, Balázs B, Duddeck H "Flavone glycosides from Polygala telephioides and Polygala arvensis" - Natural Product Letters 14(1) (1999) 35-38
  

  A novel flavone C-glucoside, telephioidin, was isolated from Polygala telephioides. Its structure was established by extensive 1D and 2D NMR measurements. Rhoifolin was isolated from Polygala arvensis and polygalitol from both plants.

  flavones, Polygala telephioides, Polygala arvensis, telephioidin, rhoifolin, apigenin, polygalitol, C-glucoside

  Publication DOI: 10.1080/10575639908045432
  Journal NLM ID: 9315615
  Publisher: Taylor & Francis Health Sciences
  Institutions: Department of Chemistry, Kakatiya University, Warangal, 506009, Andra Pradesh, India, Technical Analytical Research Group of the Hungarian Academy of Sciences, Institute for General and Analytical Chemistry of the Technical University, Szent Gellért tér 4, H-1111, Budapest, Hungary, Universität Hannover, Institut für Organische Chemie, Schneiderberg 1B, D-30167, Hannover, Germany
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, UV, optical rotation measurement, HMBC, HMQC, COSY, sulfuric acid hydrolysis
  
   
  
  Polygala arvensis
  CSDB ID 62497 (all data & tools)
• 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: 10.1211/146080899128735009
  Journal NLM ID: 9807134
  Publisher: London: Pharmaceutical Press
  Institutions: Department of Pharmaceutical Sciences, University of Antwerp, Universiteitsplein 1, B 2610, Wilrijk, Antwerp, Belgium, Faculty of Pharmacy, University of Kinshasa, B.P. 212, Kinshasa XI, Congo
  Methods: statistical analysis, antioxidant activities
  
   
  
  Morinda morindoides
  CSDB ID 62553 (all data & tools)
• 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: 10983240
  Publication DOI: 10.1007/bf02903720
  Journal NLM ID: 0376757
  Publisher: 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
  
   
  
  Daucus carota var. boissieri
  CSDB ID 62903 (all data & tools)
• 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.2000.516.20
  Institutions: 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
  
   
  
  Verbena officinalis
  CSDB ID 64986 (all data & tools)
• 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: 11237177
  Publication DOI: 10.1002/biof.5520130126
  Journal NLM ID: 8807441
  Publisher: 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
  
   
  
  Rosmarinus officinalis, Salvia officinalis
  CSDB ID 65809 (all data & tools)
• 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: 4797583
  Publication DOI: 10.1248/yakushi1947.93.9_1231
  Journal NLM ID: 0413613
  Publisher: 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
  
   
  
  Trachelospermum asiaticum var. intermedium
  CSDB ID 65916 (all data & tools)
• Article ID: 11992
  Kisiel W, Zielińska K "Sesquiterpenoids and phenolics from Lactuca perennis" - Fitoterapia 71(1) (2000) 86-87
  

  flavonoids, sesquiterpene lactone glycosides, Lactuca perennis, phenolic acid esters

  NCBI PubMed ID: 11449481
  Publication DOI: 10.1016/s0367-326x(99)00112-4
  Journal NLM ID: 16930290R
  Publisher: Elsevier
  Correspondence: Kisiel W ; Kisiel W
  Institutions: Department of Phytochemistry, Institute of Pharmacology, Polish Academy of Sciences, Krakow, Poland
  
   
  
  Lactuca perennis
  CSDB ID 66060 (all data & tools)
• 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: 10691640
  Publication DOI: 10.1021/jf991002+
  Journal NLM ID: 0374755
  Publisher: American Chemical Society
  Correspondence: longze.lin@amtbotanicals.com
  Institutions: Research Laboratory of Natural Products Chemistry, A. M. Todd Botanicals, Eugene, USA, Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, The University of Illinois at Chicago, Chicago, IL, USA
  Methods: LC-ESI-MS
  
   
  
  Trifolium pratense
  CSDB ID 66560 (all data & tools)
• 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-100100511
  Journal NLM ID: 9605507
  Publisher: 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
  
   
  
  Ixeris laevigata var. oldhami
  CSDB ID 66606 (all data & tools)
• Article ID: 12273
  Panizzi L, Catalano S, Miarelli C, Cioni PL, Campeol E "In vitro antimicrobial activity of extracts and isolated constituents of Geum rivale" - Phytotherapy Research 14(7) (2000) 561-563
  

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

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

  NCBI PubMed ID: 11054853
  Publication DOI: 10.1002/1099-1573(200011)14:7<561::aid-ptr651>3.0.co;2-h
  Journal NLM ID: 8904486
  Publisher: Chichester: Wiley
  Institutions: Dipartimento di Bioorganica e Biofarmacia, Università di Pisa, Pisa, Italy, Sezione di Biotossicologia, Dipartimento di Prevenzione A.U.S.L., Livorno, Italy
  Methods: biological assays
  
   
  
  Geum rivale
  CSDB ID 67297 (all data & tools)
• 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: 10837985
  Publication DOI: 10.1016/s0378-8741(99)00169-5
  Journal NLM ID: 7903310
  Publisher: 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
  
   
  
  Ligustrum vulgare
  CSDB ID 67356 (all data & tools)
• 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: 10904143
  Publication DOI: 10.1016/s0378-8741(00)00212-9
  Journal NLM ID: 7903310
  Publisher: Limerick: Elsevier Sequoia
  Correspondence: a.b.samuelsen@farmasi.uio.no
  Institutions: Department of Pharmacognosy, School of Pharmacy, University of Oslo, Oslo, Norway
  
   
  
  Plantago major
  CSDB ID 67653 (all data & tools)
• 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: 33863030
  Publication DOI: 10.1046/j.1469-8137.2000.00743.x
  Journal NLM ID: 9882884
  Publisher: 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
  
   
  
  Phillyrea latifolia
  CSDB ID 68164 (all data & tools)
• 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: 10996263
  Publication DOI: 10.1016/s0305-1978(00)00013-2
  Journal NLM ID: 0430442
  Publisher: 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
  
   
  
  Lavandula stoechas ssp. stoechas, Lavandula stoechas ssp. luisieri, Lavandula viridis, Lavandula dentata var. dentata, Lavandula angustifolia ssp. angustifolia, Lavandula angustifolia ssp. pyrenaica, Lavandula angustifolia ssp. delphinensis, Lavandula lanata, Lavandula latifolia, Sabaudia atriplicifolia, Lavandula stoechas ssp. atlantica, Lavandula stoechas ssp. cariensis, Lavandula stoechas ssp. lusitanica, Lavandula stoechas ssp. pedunculata, Lavandula stoechas ssp. sampaiana, Lavandula dentata var. candicans
  CSDB ID 68279 (all data & tools)
• Article ID: 12571
  Yoshikawa M, Uemura T, Shimoda H, Kishi A, Kawahara Y, Matsuda H "Medicinal foodstuffs. XVIII. Phytoestrogens from the aerial part of Petroselinum crispum Mill. (Parsley) and structures of 6''-acetylapiin and a new monoterpene glycoside, petroside" - Chemical and Pharmaceutical Bulletin 48(7) (2000) 1039-1044
  

  In the course of our screening for natural estrogenic compounds from Occidental medicinal herbs, the extracts of several herbs were found to show proliferative activity in MCF-7 (an estrogen-sensitive breast cancer cell line). Among these active herbs, the methanolic extract from the aerial parts of Petroselinum crispum (parsley) showed potent estrogenic activity, which was equal to that of isoflavone glycosides from soybean. Through bioassay-guided separation, we isolated several flavone glycosides and a new flavone glycoside, 6"-acetylapiin, with estrogenic activity together with a new monoterpene glucoside, petroside. The structures of 6"-acetylapiin and petroside were characterized by the chemical and physicochemical evidence. Estrogenic activities of these flavone glycosides were found to be enhanced by removal of their glycoside moieties. The EC50 values (concentration needed to enhance the MCF-7 proliferation 50% compared to non-estrogen treated cell) of their aglycones are as follows, apigenin (1.0 μM), diosmetin (2.9 μM), and kaempferol (0.56 μM). The estrogenic activities of these flavones are nearly equal to those of the isoflavones, daidzein (0.61 μM) and genistein (0.60 μM). The methanolic extract of parsley, apiin, and apigenin restored the uterus weight in ovariectomized mice when orally administered for consecutive 7 days.

  flavone glycoside, phytoestrogen, Petroselinum crispum, 6"-acetylapiin, petroside, breast cancer cell line

  NCBI PubMed ID: 10923837
  Publication DOI: 10.1248/cpb.48.1039
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Correspondence: Yoshikawa M
  Institutions: Kyoto Pharmaceutical University, Kyoto, Japan, Research and Development Division, Morishita Jintan Co., Ltd., Osaka, Japan
  Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, TLC, ESI-MS, biological assays, HPLC, extraction, column chromatography
  
   
  
  Petroselinum crispum
  CSDB ID 68829 (all data & tools)
• 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: 10683879
  Journal NLM ID: 9800766
  Publisher: 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
  
   
  
  Ligustrum vulgare
  CSDB ID 68912 (all data & tools)

Show legend Show as text

Structure type: monomer ; 467.0961 [M+Na]+
Trivial name: apigenin-7-O-b-D-glucuronopyranoside
Compound class: glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_423153,IEDB_613414

• Article ID: 9015
  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
  
   
  
  Hypsizygus tessulatus var. white
  CSDB ID 51093 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: vitexin, isovitexin
Compound class: saponin glycoside, glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_613414

• Article ID: 9741
  Idaka K, Hirai Y, Shoji J "Studies on the constituents of Palmae plants. IV. the constituents of the leaves of Sabal causiarum Becc" - Chemical and Pharmaceutical Bulletin 36 (1988) 1783-1790
  

  The constituents of the leaves of Sabal causiarum BECC. have been investigated. Vitexin, methyl proto-deltonin, methyl proto-causiaroside I(=26-O-β-D-glucopyranosyl 22-O-methyl-25(R)-furost-5-en-3β,26-diol 3-O-[α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→4)][α-L-rhamnopyranosyl(1→2)]-β-D-glucopyranoside) and causiaroside II(=3β,16β-dihydroxypregn-5-en-20-one 3-O-[α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosy(1→4)][α-L-rhamnopyranosyl(1→2)]-β-D-glucopyranosyl 16-O-[δ-(β-D-glucopyranosyloxy)-γ-methyl]-valerate) were isolated and identified. This is the first isolation and characterization of the latter two compounds from a natural source, and these results are interesting from the standpoint of the biogenesis of the steroidal glycosides of the Palmae plants.

  steroidal saponin, Palmae, Sabal causiarum, methyl proto-deltonin, methyl proto-causiaroside I, causiaroside II, 20, 22-secofurostanol, C-glycosyl flavonoid, vitexin

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003626991
  Publisher: Pharmaceutical Society Of Japan
  Institutions: School of Pharmaceutical Sciences, Showa University, Japan
  Methods: gel filtration, 13C NMR, 1H NMR, IR, TLC, acid hydrolysis, GLC, methanolysis, enzymatic digestion, partial methanolysis, methylation analysis, melting point determination, acetylation analysis
  
   
  
  Sabal causiarum
  CSDB ID 219440 (all data & tools)
• 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: 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 67688 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: 6'''-feruloylsaponarin
Compound class: flavonol glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_613414,IEDB_983931,SB_192

• Article ID: 9768
  Ohkawa M, Kinjo J, Hagiwara Y, Hagiwara H, Ueyama H, Nakamura K, Ishikawa R, Ono M, Nohara T "Three new anti-oxidative saponarin analogs from young green Barley leaves" - Chemical and Pharmaceutical Bulletin 46(12) (1998) 1887-1890
  

  Three new saponarin analogs, 6'''-sinapoylsaponarin, 6'''-feruloysaponarin and 4'-glucosyl-6'''-sinapoyl-saponarin were isolated together with four known compounds from young green barley (Hordeum vulgare var. nudum) leaves. Their anti-oxidative effects towards superoxide, photo-oxidation of vitamins and the 1,1-diphenyl-2-picrylhydrazyl radical were tested. The superoxide-scavenging activity depended on the number of free hydroxy groups. In contrast, the inhibition of vitamin oxidation seemed to be due to the flavone skeleton. In addition, the sinapoyl moiety seemed to be important for radical-scavenging activity.

  Publication DOI: 10.1248/cpb.46.1887
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, Hagiwara Institute of Health, Japan Pharmaceutical Development Co. Ltd., Faculty of Research Institute of General Education, Kyushu Tokai University
  Methods: 13C NMR, 1H NMR, UV, HR positive FAB-MS, positive FAB-MS
  
   
  
  Hordeum vulgare var. nudum
  CSDB ID 121041 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: 4'-glucosyl-6'''-sinapoylsaponarin
Compound class: flavonol glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_613414,IEDB_983931,SB_192

• Article ID: 9768
  Ohkawa M, Kinjo J, Hagiwara Y, Hagiwara H, Ueyama H, Nakamura K, Ishikawa R, Ono M, Nohara T "Three new anti-oxidative saponarin analogs from young green Barley leaves" - Chemical and Pharmaceutical Bulletin 46(12) (1998) 1887-1890
  

  Three new saponarin analogs, 6'''-sinapoylsaponarin, 6'''-feruloysaponarin and 4'-glucosyl-6'''-sinapoyl-saponarin were isolated together with four known compounds from young green barley (Hordeum vulgare var. nudum) leaves. Their anti-oxidative effects towards superoxide, photo-oxidation of vitamins and the 1,1-diphenyl-2-picrylhydrazyl radical were tested. The superoxide-scavenging activity depended on the number of free hydroxy groups. In contrast, the inhibition of vitamin oxidation seemed to be due to the flavone skeleton. In addition, the sinapoyl moiety seemed to be important for radical-scavenging activity.

  Publication DOI: 10.1248/cpb.46.1887
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, Hagiwara Institute of Health, Japan Pharmaceutical Development Co. Ltd., Faculty of Research Institute of General Education, Kyushu Tokai University
  Methods: 13C NMR, 1H NMR, UV, HR positive FAB-MS, positive FAB-MS
  
   
  
  Hordeum vulgare var. nudum
  CSDB ID 121042 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: 6'''-sinapoylsaponarin
Compound class: flavonol glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_613414,IEDB_983931,SB_192

• Article ID: 9768
  Ohkawa M, Kinjo J, Hagiwara Y, Hagiwara H, Ueyama H, Nakamura K, Ishikawa R, Ono M, Nohara T "Three new anti-oxidative saponarin analogs from young green Barley leaves" - Chemical and Pharmaceutical Bulletin 46(12) (1998) 1887-1890
  

  Three new saponarin analogs, 6'''-sinapoylsaponarin, 6'''-feruloysaponarin and 4'-glucosyl-6'''-sinapoyl-saponarin were isolated together with four known compounds from young green barley (Hordeum vulgare var. nudum) leaves. Their anti-oxidative effects towards superoxide, photo-oxidation of vitamins and the 1,1-diphenyl-2-picrylhydrazyl radical were tested. The superoxide-scavenging activity depended on the number of free hydroxy groups. In contrast, the inhibition of vitamin oxidation seemed to be due to the flavone skeleton. In addition, the sinapoyl moiety seemed to be important for radical-scavenging activity.

  Publication DOI: 10.1248/cpb.46.1887
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, Hagiwara Institute of Health, Japan Pharmaceutical Development Co. Ltd., Faculty of Research Institute of General Education, Kyushu Tokai University
  Methods: 13C NMR, 1H NMR, UV, HR positive FAB-MS, positive FAB-MS
  
   
  
  Hordeum vulgare var. nudum
  CSDB ID 121043 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: saponarin
Compound class: glycoside, flavonoid glycoside, flavonol glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_613414,IEDB_983931,SB_192

• Article ID: 9768
  Ohkawa M, Kinjo J, Hagiwara Y, Hagiwara H, Ueyama H, Nakamura K, Ishikawa R, Ono M, Nohara T "Three new anti-oxidative saponarin analogs from young green Barley leaves" - Chemical and Pharmaceutical Bulletin 46(12) (1998) 1887-1890
  

  Three new saponarin analogs, 6'''-sinapoylsaponarin, 6'''-feruloysaponarin and 4'-glucosyl-6'''-sinapoyl-saponarin were isolated together with four known compounds from young green barley (Hordeum vulgare var. nudum) leaves. Their anti-oxidative effects towards superoxide, photo-oxidation of vitamins and the 1,1-diphenyl-2-picrylhydrazyl radical were tested. The superoxide-scavenging activity depended on the number of free hydroxy groups. In contrast, the inhibition of vitamin oxidation seemed to be due to the flavone skeleton. In addition, the sinapoyl moiety seemed to be important for radical-scavenging activity.

  Publication DOI: 10.1248/cpb.46.1887
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, Hagiwara Institute of Health, Japan Pharmaceutical Development Co. Ltd., Faculty of Research Institute of General Education, Kyushu Tokai University
  Methods: 13C NMR, 1H NMR, UV, HR positive FAB-MS, positive FAB-MS
  
   
  
  Hordeum vulgare var. nudum
  CSDB ID 121044 (all data & tools)
• Article ID: 12240
  Nørbæk R, Brandt K, Kondo T "Identification of flavone C-glycosides including a new flavonoid chromophore from barley leaves (Hordeum vulgare L.) by improved NMR techniques" - Journal of Agricultural and Food Chemistry 48(5) (2000) 1703-1707
  

  Six flavone C-glycosides were isolated from young leaves of barley. One of the C-glucosides has a new type of nucleus, a 2‘,4‘,5,5‘,7-penta-OH-substituted flavone bearing a 6-C-β-d-glucoside, which has apparently never been isolated before. One mono- and two di-C-glycosyl flavones were isolated for the first time from barley and identified as isoscoparin 7-O-β-d-glucoside, carlinoside, and shaftoside, respectively. Other flavones were 7-O-β-d-glucosides of isoorientin and isovitexin. The known problematic NMR structure elucidation of C-glycosyl flavonoids has been solved by using both a temperature close to the freezing point of the solvent (22.5 °C in DMSO-d6) and a high temperature (70, 90 °C) for comparison during NMR measurements. Structural determination of all the compounds was achieved by employing 1D and 2D NMR techniques.

  NOE, barley; Hordeum vulgare; C-glycosyl flavone; phenolic hydroxyl group; NMR

  NCBI PubMed ID: 10820082
  Publication DOI: 10.1021/jf9910640
  Journal NLM ID: 0374755
  Publisher: American Chemical Society
  Correspondence: rikke.norbaek@agrsci.dk
  Institutions: Danish Institute of Agricultural Sciences, Department of Fruit, Vegetable and Food Science, Aarslev, Denmark, Chemical Instrument Center, Nagoya University, Nagoya, Japan
  Methods: 13C NMR, 1H NMR, TLC, ESI-MS, HPLC, extraction, derivatization, evaporation, HR-EI-MS
  
   
  
  Hordeum vulgare cv. Alexis
  CSDB ID 67166 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: isovitexin 4',7-diglucoside
Compound class: flavonol glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_613414,IEDB_983931,SB_192

• Article ID: 9768
  Ohkawa M, Kinjo J, Hagiwara Y, Hagiwara H, Ueyama H, Nakamura K, Ishikawa R, Ono M, Nohara T "Three new anti-oxidative saponarin analogs from young green Barley leaves" - Chemical and Pharmaceutical Bulletin 46(12) (1998) 1887-1890
  

  Three new saponarin analogs, 6'''-sinapoylsaponarin, 6'''-feruloysaponarin and 4'-glucosyl-6'''-sinapoyl-saponarin were isolated together with four known compounds from young green barley (Hordeum vulgare var. nudum) leaves. Their anti-oxidative effects towards superoxide, photo-oxidation of vitamins and the 1,1-diphenyl-2-picrylhydrazyl radical were tested. The superoxide-scavenging activity depended on the number of free hydroxy groups. In contrast, the inhibition of vitamin oxidation seemed to be due to the flavone skeleton. In addition, the sinapoyl moiety seemed to be important for radical-scavenging activity.

  Publication DOI: 10.1248/cpb.46.1887
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, Hagiwara Institute of Health, Japan Pharmaceutical Development Co. Ltd., Faculty of Research Institute of General Education, Kyushu Tokai University
  Methods: 13C NMR, 1H NMR, UV, HR positive FAB-MS, positive FAB-MS
  
   
  
  Hordeum vulgare var. nudum
  CSDB ID 121045 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: isovitexin 7-rhamnosylglucoside
Compound class: flavonol glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144144,IEDB_146664,IEDB_225177,IEDB_613414,IEDB_885823,IEDB_983931,SB_192

• Article ID: 9768
  Ohkawa M, Kinjo J, Hagiwara Y, Hagiwara H, Ueyama H, Nakamura K, Ishikawa R, Ono M, Nohara T "Three new anti-oxidative saponarin analogs from young green Barley leaves" - Chemical and Pharmaceutical Bulletin 46(12) (1998) 1887-1890
  

  Three new saponarin analogs, 6'''-sinapoylsaponarin, 6'''-feruloysaponarin and 4'-glucosyl-6'''-sinapoyl-saponarin were isolated together with four known compounds from young green barley (Hordeum vulgare var. nudum) leaves. Their anti-oxidative effects towards superoxide, photo-oxidation of vitamins and the 1,1-diphenyl-2-picrylhydrazyl radical were tested. The superoxide-scavenging activity depended on the number of free hydroxy groups. In contrast, the inhibition of vitamin oxidation seemed to be due to the flavone skeleton. In addition, the sinapoyl moiety seemed to be important for radical-scavenging activity.

  Publication DOI: 10.1248/cpb.46.1887
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, Hagiwara Institute of Health, Japan Pharmaceutical Development Co. Ltd., Faculty of Research Institute of General Education, Kyushu Tokai University
  Methods: 13C NMR, 1H NMR, UV, HR positive FAB-MS, positive FAB-MS
  
   
  
  Hordeum vulgare var. nudum
  CSDB ID 121046 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: vitexin, isovitexin
Compound class: glycoside, flavonoid glycoside, flavonol glycoside
Contained glycoepitopes: IEDB_613414

• Article ID: 9768
  Ohkawa M, Kinjo J, Hagiwara Y, Hagiwara H, Ueyama H, Nakamura K, Ishikawa R, Ono M, Nohara T "Three new anti-oxidative saponarin analogs from young green Barley leaves" - Chemical and Pharmaceutical Bulletin 46(12) (1998) 1887-1890
  

  Three new saponarin analogs, 6'''-sinapoylsaponarin, 6'''-feruloysaponarin and 4'-glucosyl-6'''-sinapoyl-saponarin were isolated together with four known compounds from young green barley (Hordeum vulgare var. nudum) leaves. Their anti-oxidative effects towards superoxide, photo-oxidation of vitamins and the 1,1-diphenyl-2-picrylhydrazyl radical were tested. The superoxide-scavenging activity depended on the number of free hydroxy groups. In contrast, the inhibition of vitamin oxidation seemed to be due to the flavone skeleton. In addition, the sinapoyl moiety seemed to be important for radical-scavenging activity.

  Publication DOI: 10.1248/cpb.46.1887
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, Hagiwara Institute of Health, Japan Pharmaceutical Development Co. Ltd., Faculty of Research Institute of General Education, Kyushu Tokai University
  Methods: 13C NMR, 1H NMR, UV, HR positive FAB-MS, positive FAB-MS
  
   
  
  Hordeum vulgare var. nudum
  CSDB ID 121047 (all data & tools)
• Article ID: 12335
  Sakushima A, Maoka T, Ohno K, Coskun M, Guvenc A, Erdurak CS, Ozkan AM, Seki K-i, Ohkura K "Major antioxidative substances in Boreava orientalis (Cruciferae)" - Natural Product Letters 14(6) (2000) 441-446
  

  Antioxidative activities for lipid peroxidation of C-glycosylflavones isolated from the fruits of Boreava orientalis and related compounds were studied. C-glycosylflavones, especially isovitexin and isoorientin, were found to be antioxidative constituents of the fruits of B. orientulis. The activity of isoorientin was stronger than that of isovitexin.

  antioxidative activity, fruits, Cruciferae, isoorientin, Boreava orientalis, phenol compounds, C-glycosylflavone, isovitexin, benzofuran lignan

  Publication DOI: 10.1080/10575630008043782
  Journal NLM ID: 9315615
  Publisher: Taylor & Francis Health Sciences
  Institutions: Kyoto Pharmaceutical University, Kyoto, Japan, Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Japan, Department of Pharmaceutical Botany, Faculty of Pharmacy, Ankara University, Ankara, Turkey
  Methods: HPLC, extraction, antioxidation activities
  
   
  
  Boreava orientalis
  CSDB ID 67630 (all data & tools)
• 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: 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 67689 (all data & tools)