Two New Stilbene Dimer Glucosides from Grape (Vitis vinifera) Cell Cultures

Abstract

Two new stilbene dimer glucosides, resveratrol (E)-dehydrodimer 11-O-β-d-glucopyranoside (1) and resveratrol (E)-dehydrodimer 11‘-O-β-d-glucopyranoside (2), were isolated together with the known resveratrol (E)-dehydrodimer (3) and pallidol (4) from Vitis vinifera cell cultures. The structures and stereochemistry of the new compounds were determined on the basis of spectroscopic data analysis. Compounds 1 and 2 are dimers that belong to a new type of oligostilbene formed from a resveratrol unit and a resveratrol glucoside unit. Compounds 1 and 3 exhibited nonspecific inhibitory activity against cyclooxygenase-1 and -2, with IC₅₀ values in the range of 5 μM, whereas compound 4 was approximately 10-fold less active.