Procyanidin dimers and trimers from grape seeds

doi:10.1016/S0031-9422(00)95213-0

Phytochemistry

Volume 30, Issue 4, 1991, Pages 1259-1264

https://doi.org/10.1016/S0031-9422(00)95213-0 Get rights and content

Abstract

Fractionation of a grape (Vitis vinifera) seed extract yielded various natural procyanidin dimers and trimers isolated and identified for the first time in grapes: procyanidin dimers B5 [epicatechin-(4β → 6)-epicatechin], B6 [catechin-(4α → 6)-catechin] and B8 [catechin-(4α → 6)-epicatechin]; four procyanidin trimers [epicatechin-(4β → 6)-epicatechin-(4β → 8)-epicatechin], [epicatechin-(4β → 8)-epicatechin-(4β → 6)-catechin], [epicatechin-(4β → 8)-epicatechin-(4β → 6)-epicatechin], [epicatechin-(4β → 6)-epicatechin-(4β → 8)-catechin] along with five galloyl procyanidins: B2 3-O-gallate, B1 3-O-gallate, B4 3′-O-gallate, B2 3,3′-di-O-gallate and [epicatechin-(4β → 8)-epicatechin 3-O-gallate-(4β → 8)-catechin]. The presence of (+)-catechin, (−)-epicatechin, (−)-epicatechin 3-O-gallate, procyanidins dimers B1, B2, B3, B4, B7, B2 3′-O-gallate and procyanidin trimers C1 and [epicatechin-(4β → 8)-epicatechin-(4β → 8)-catechin] was also confirmed. The structures of all these compounds were elucidated by enzymatic hydrolysis, complete acid hydrolysis, partial acid-catalysed degradation with phloroglucinol and phenylmethanethiol, FABMS and ¹H NMR. Separation of procyanidins and of their phloroglucinol or phenylmethanethiol adducts was achieved by TLC on silica plates and HPLC.

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Procyanidin dimers and trimers from grape seeds

Abstract

J. Chromatogr.

Am. -J. Enol. Vitic.

Phytochemistry

Phytochemistry

Liebigs Ann. Chem. Dtsch.

Ann. Chim. (Rome)

Am. J. Enol. Vitic.

Phytochemistry

Phytochemistry

Phytochemistry

Bull. O.I.V.

Am. J. Enol. Vitic.

J. Agric. Food Chem.

Phytochemistry