Lignan and phenylpropanoid glycerol glucosides in wine

Abstract Three glycoconjugates, 1-O-(β- D -glucopyranosyl)-2-[2-methoxy-4-(ω-hydroxypropyl)-phenoxy]-propan-3-ol, 1,2,3,4-tetrahydro-7-hydroxy-1-(4′-β-glucopyranosyl-3′-metho1xyphenyl)-6-methoxy-2,3-naphthalenedimethanol (isolariciresinol-β-4′-O-glucopyranoside) and, tentatively, 2,3-bis(4′-hydroxy-3′-methoxybenzyl)-butane-1,4-diol-β- D -glucoside (seco-isolariciresinol-β- D -glucoside) have been detected in Riesling wine by FAB-mass spectrometry/mass spectrometry and subsequently isolated and identified by spectral and chemical studies. The first of these compounds is a new shikimic acid metabolite of wine, and the latter two lignans represent a new category of wine phenols.