Anti-inflammatory tetramers of resveratrol from the roots of Vitis amurensis and the conformations of the seven-membered ring in some oligostilbenes

Five resveratrol tetramers, amurensins I-M, were isolated from the roots of Vitis amurensis (Rupr.), together with five known resveratrol tetramers, (+)-hopeaphenol, isohopeaphenol, vitisin A, (+)-vitisifuran A, and heyneanol A. Their structures and stereochemistry were determined by chemical and spectroscopic methods, especially by use of 2D NMR analysis. Some-of them had an ampelopsin A or a balanocarpol unit, in which the conformations of the seven-membered carbon ring were described for the first time. The anti-inflammatory activities of the tetramers were also tested. Among them, (+)-hopeaphenol, isohopeaphenol, vitisin A, (+)-vitisifuran A and heyneanol A showed potent inhibition on the biosynthesis of leukotriene B-4 (LTB4), and amurensins I and L showed strong antagonism of the histamine acceptor. (C) 2001 Elsevier Science Ltd. All rights reserved.