C-Glycosylflavones from Avena sativa

Chopin, Jean; Dellamonica, G.; Bouillant, Marie‐Louise; Besset, A.; Popovici, Gheorghe; Weissenböck, Gottfried

doi:10.1016/0031-9422(77)80131-3

Cited by 47 publications

(20 citation statements)

References 11 publications

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“…Avena sativa is used in European folk medicine for rheumatism, gout, liver-and skin diseases (Schneider, 1985). It contains saponins, C-glycosyl flavones, flavonoid-O-glycosides (Chopin et al, 1977). Wenzig et al (2005) isolated three flavano -lignans salcolin A and B and neohydnocarpin.…”

Section: Poaceaementioning

confidence: 99%

Medicinal herbs for the treatment of rheumatic disorders—A survey of European herbals from the 16th and 17th century

Adams

Berset

Kessler

et al. 2009

Journal of Ethnopharmacology

177

105

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Section: Poaceaementioning

confidence: 99%

Medicinal herbs for the treatment of rheumatic disorders—A survey of European herbals from the 16th and 17th century

Adams

Berset

Kessler

et al. 2009

Journal of Ethnopharmacology

177

105

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“…TLC was performed on microcrystalline cellulose (Machery & Nagel, Diiren) using the following solvent systems: (I) chloroform/acetic acid (3 :2, v/v), saturated with water; (11) 15 % acetic acid; (111) n-butanol/acetic/acid/water (5:2: 3, v/v/v).…”

Section: Thin-layer Chromatography Systemsmentioning

confidence: 99%

Purification, characterization, and kinetic mechanism of S‐adenosyl‐l‐methionine: vitexin 2″‐O‐rhamnoside 7‐O‐methyltransferase of Avena sativa L

Knogge

Weissenböck

1984

European Journal of Biochemistry

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An 0-methyltransferase catalyzing the transfer of the methyl group of S-adenosyl-L-methionine to the A-ring 7-hydroxyl group of vitexin 2"-O-rhamnoside has been isolated from oat primary leaves and purified 180-fold by protein fractionation with (NH,),S04 and chromatography on DEAE-cellulose and S-adenosyl-L-homocysteinesepharose. K, values for S-adenosyl-L-methionine and the flavonoid substrate were 1.6 pM and 15 pM, respectively. The lack of methyl transfer to biosynthetic intermediates suggests that the reaction is the last step in the biosynthetic pathway to the oat flavonoid 7-0-methylvitexin 2"-0-rhamnoside. Based on results obtained from kinetic inhibition studies and affinity chromatography a mono-iso Theorell-Chance mechanism is proposed with the nucleotide substrate binding before the flavonoid.Methylation of high and low-molecular-mass substances is a very abundant reaction in animal and plant tissues. The reversible covalent modification of proteins by methyltransfer via S-adenosyl-L-methionine as well as the methylation of DNA and RNAs are discussed as possible tools in cellular regulation [l -31. In plants methyl groups are very common substituents of secondary products. Several N-methyltransferases participate in alkaloid biosynthesis [4]. 0-Methyltransferases are involved in the biosynthesis of plant phenolics [5]. Particularly, numerous flavonoids are known which possess methoxyl groups at different positions of the A and B rings as well as in the 3 position of the heterocycle.Oat is frequently used as test object both in plant physiology and pathology. Several physiological reponses of the plant to light as well as one of the photoreceptors, the phytochrome system, are well known [6,7]. On the other hand, this plant is intensively investigated in the context of its rust diseases [8]. For both fields of research flavonoid biosynthesis could be of special interest.Flavonoids in general are suggested to have a function in the protection of plants against ultraviolet light [9]. Their biosynthesis, at least in part, is photo-controlled [lo]. In oat primary leaves three major flavonoid compounds accumulate : an isovitexin derivative and two structurally related vitexin derivatives one of which is methylated at the 7-hydroxyl group [Ill (Fig. 1). The latter is suggested to be a preformed antifungal substance [8].Whereas several enzymes have been isolated which catalyze the methyl transfer to the 3' position of 3',4'-dihydroxyflavonoids or to the 3 position of flavonols, only very few reports exist on para-methylation of B-ring (4') monoAbbreviations. MVR, 7-0-methylvitexin 2"-0-rhamnoside; VR, vitexin 2"-0-rhamnoside; AdoMet, S-adenosyl-L-methionine; AdoHcy, S-adenosyl-r -homocysteine; TLC, thin-layer chromatography.Enzyme. Flavonoid 0-methyltransferdse, AdoMet : vitexin 2"-0-rhamnoside 7-0-methyltransferase (EC 2.1.1 .-), R2= C-Glc-0-Rha, R3 = H : 7-0-methylvitexin 2-0-rhamnoside (MVR) ; R, = R2 = R3 = H : apigenin, R, = R, = H, R, = C-Glc : vitexin; R1 =CH3, R,=C-Glc, R,=H: 7-0-methylvitexin; R, ...

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“…3c, d). Comparison with data reported in the literature about flavonoids isolated in oat suggested the assignment of peak 1 as isoorientin 2-O-glucoside (Chopin et al 1977) and peak 2 as isovitexin 2 00 -O-arabinoside (Saleh et al 1988). The structures are shown in Fig.…”

Section: Identification Of Allelochemical Agentsmentioning

confidence: 73%

“…Analysis of the flavonoid fraction by ESI-MS led to the identification of the flavone C-glycosides isoorientin 2-Oglucoside and isovitexin 2 00 -O-arabinoside which have been previously described from oat (Chopin et al 1977;Saleh et al 1988). …”

Section: Discussionmentioning

confidence: 99%

Bioassay-guided isolation of allelochemicals from Avena sativa L.: allelopathic potential of flavone C-glycosides

et al. 2009

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The allelopathic potential of oat (Avena sativa L., var. Argentina, Poaceae, Cyperales) was investigated under field and laboratory conditions. In field trials, oat plants provided an effective control of weeds, showing a species-specific impact: the most abundant weed species, Picris echioides was reduced by 94% in number of individuals. Aerial parts of oat plants, harvested immediately before soil incorporation, were utilized in a bioassay-guided isolation, which was aimed at identifying the phytotoxic compounds in a methanol/water extract of the aerial parts of the plants. Further partitions of extract gave an active n-butanol portion composed of flavonoids and saponins. Phytotoxic activity was detected for the flavonoid fraction, whereas no activity was found for the saponin mixture. Germination of an indicator species, lettuce (Lactuca sativa L.), was completely inhibited at flavonoid concentrations of 6.7, 10.0, and 20.0 mg/mL, and conversely the number of abnormal seedlings was greatly increased from 2% of control to over 96% at concentrations equal to 6.7 and 10.0 mg/mL. Analysis of the flavonoid fraction by ESI-MS techniques identified two components of the mixture as isoorientin 2-O-glucoside and isovitexin 2″-O-arabinoside. Saponins were characterized as avenacoside A, avenacoside B, 26-desglucoavenacoside A, and 26-desglucoavenacoside B. Both flavone C-glycosides and saponins were isolated previously from oat

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C-Glycosylflavones from Avena sativa

Cited by 47 publications

References 11 publications

Medicinal herbs for the treatment of rheumatic disorders—A survey of European herbals from the 16th and 17th century

Medicinal herbs for the treatment of rheumatic disorders—A survey of European herbals from the 16th and 17th century

Purification, characterization, and kinetic mechanism of S‐adenosyl‐l‐methionine: vitexin 2″‐O‐rhamnoside 7‐O‐methyltransferase of Avena sativa L

Bioassay-guided isolation of allelochemicals from Avena sativa L.: allelopathic potential of flavone C-glycosides

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