453. Bergenin, a C-glycopyranosyl derivative of 4-O-methylgallic acid

Hay, J. Evelyn; Haynes, L. J.

doi:10.1039/jr9580002231

Cited by 57 publications

(29 citation statements)

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“…3) by 2D 1 H and 13 C NMR. This compound has been previously isolated from roots of Bergenia crassifolia [20]. Compound 2 showed a quasimolecular ion at m/z [M-H] + 448 and MS-MS products (m/z 301, 257, 229 and 185) that correspond to ellagic acid in its ESI-MS.…”

Section: Resultsmentioning

confidence: 97%

Investigating glucosyltransferase inhibitory activities of polyphenols from kapur (Dryobalanops sp.) heartwood extracts

et al. 2007

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The inhibitory effects of 50% aqueous ethanol extracts obtained from 36 tropical woody plants species on glucosyltransferase (GTase) activity were studied. Out of the 36 species examined, those obtained from kapur (Dryobalanops sp.), a species growing in Kalimantan (Indonesia), showed the highest level of GTase inhibition. Kapur extracts were further subjected to fractionation using column chromatography (LH-20 gel, cellulose and C-18 silica gel column). LH-20 gel provided the most successful method of fractionation. The separated fractions showed positive with Folin-Ciocalteau's reagent and negative with vanillin-HCl reagent, indicating that the main constituents of the active fractions were polyphenols but not proanthocyanidin (condensed tannins). Results of the assay for protein precipitating ability with bovine serum albumin (BSA) solution suggested these polyphenols have strong protein-precipitating ability. The predominant compound produced after acid hydrolysis was ellagic acid, indicating that the GTase-inhibitory components were mainly ellagitannins. Two polyphenolic compounds referred to as compounds 1 and 2 were isolated from the water eluate fraction with LH-20 gel column, and these compounds showed comparatively strong GTaseinhibitory activities and relatively low molecular weight. Using a combination of two-dimensional, 1 H and 13 C nuclear magnetic resonance analysis, compound 1 was identified as 4-methoxy-2-[tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)pyran-2-yl]-a-resorcylic acid d-lactone (ber genin), and 2 was identified as 4-O-(a-rhamnopyranosyl) ellagic acid (eschweilenol C). Bergenin has been previously isolated from the roots of Bergenia crassifolia, and eschweilenol C has been isolated from the bark of Eschweilera coriacea. Both compounds were found in kapur for the first time.

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Section: Resultsmentioning

confidence: 97%

Investigating glucosyltransferase inhibitory activities of polyphenols from kapur (Dryobalanops sp.) heartwood extracts

et al. 2007

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“…The UV spectrum showed characteristic absorptions at 220 and 274 nm for methyl 4-O-methylgallate [9]. It did not display any shift with either AcONa or B(OH) 3 Table 2, and their correlations are shown in Fig.…”

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confidence: 86%

Biologically Active Bergenin Derivatives from Bergenia stracheyi

Siddiq

Fatima

Malik

et al. 2012

Chemistry & Biodiversity

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New bergenin derivatives, bergecins A and B (1 and 2, resp.), have been isolated from the AcOEt-soluble fraction of Bergenia stracheyi, along with bergenin (3), and their structures were elucidated on the basis of (1) H- and (13) C-NMR spectra, and by COSY, HMQC, and HMBC experiments. Compound 2 showed potent inhibitory potential against the enzyme lipoxygenase, while 1 was moderately active. On the other hand, both compounds exhibited significant antioxidant activities in 1,1-diphenyl-2-picrylhydrazyl (DPPH) scavenging assay.

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“…In this context the unique structures assigned to vescalin and vescalagin (43,44), castalin and castalagin (41,42), valolaginic acid and isovalolaginic acid (49,51), which are based upon the openchain conformation of the D-glucose molecule, are worthy of comment and particular attention. It is also interesting to note that all these latter polyphenols contain a distinctive structural feature -namely that of a c-glycoside -analogous to that of the c-glucoside bergenin (30). Where a relationship can be discerned (e. g. Chebulinic acid and Chebulagic acid in Myrabolans) this usually involves an extension of one of the basic patterns of gallic acid metabolism (A, B or C) outlined above.…”

Section: Mallotus Japonicusmentioning

confidence: 97%

“…Determination of the absolute configuration of ( + )-hexamethoxydiphenic acid, (33,62) eclipsed conformation of the ester carbonyl oxygen and the adjacent hydrogen atom on the glucose ring (30), and (ii) that in the hexahydroxydiphenoyl group there is a preference for the anti or opposed arrangement of the two carbonyl groups with the C-O dipoles aligned antiparallel (31). O······H ~O~ (30) If these two features dominate the oxidative coupling reactions of galloyl esters of D-glucose then the geometrical restrictions imposed by the sugar ring lead directly to the conclusion that the chirality of the derived hexahydroxydiphenoyl group is determined by the sugar. Molecular models show that the 3,6-bridges [e. g. corilagin (28)] have the R-configuration and 4,6 or 2,3 hexahydroxydiphenoyl linkages (e. g. pedunculagin) have the alternative s configuration.…”

Section: Hexahydroxydiphenoyl Estersmentioning

confidence: 99%

The Metabolism of Gallic Acid and Hexahydroxydiphenic Acid in Higher Plants

Haslam

1982

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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453. Bergenin, a C-glycopyranosyl derivative of 4-O-methylgallic acid

Cited by 57 publications

References 0 publications

Investigating glucosyltransferase inhibitory activities of polyphenols from kapur (Dryobalanops sp.) heartwood extracts

Investigating glucosyltransferase inhibitory activities of polyphenols from kapur (Dryobalanops sp.) heartwood extracts

Biologically Active Bergenin Derivatives from Bergenia stracheyi

The Metabolism of Gallic Acid and Hexahydroxydiphenic Acid in Higher Plants

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