Sulfonation of procyanidin polymers: Evidence of intramolecular rearrangement and aromatic ring substitution

초록

The reaction of Douglas-fir polymeric procyanidins with aqueous sodium hydrogen sulfite was investigated by gel permeation chromatography (GPC) and the Isolation and Identification of sulfonated derivatives. GPC profiles of molecular weight over time indicated that epicatechin-(4β)-sulfonate was rapidly formed initially but did not significantly increase over longer reaction time. Undefined oligomeric materials remained in the reaction mixture, which suggests that other reactions compete with simple acid-catalyzed cleavage of the interflavanoid bond and subsequent formation of 4-substituted flavanoid sulfonates. The Isolation of disodium epicatechin-(4, 5')-disulfonate and a functionalized chromene derivative gave evidence that aromatic ring Sulfonation and flavanoid C-ring isomerization are two such reactions. © 1994 Walter de Gruyter

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