Isolation, Identification, and Antioxidant Activity of Three Stilbene Glucosides Newly Extracted from Vitis vinifera Cell Cultures

Suspension cultures of Vitis vinifera L. (Vitaceae) produce many hydroxylated stilbene glucosides found in red wine. From these cells, we isolated and characterized glycosylated stilbenes, (Z)-piceatannol (3,5,3',4'-tetrahydroxystilbene) -3-O-beta-d-glucopyranoside (6) and (E)- and (Z)-resveratrol (3,5, 4'-trihydroxystilbene)-4'-O-beta-d-glucopyranoside (2 and 7, respectively), which have not previously reported to be constituents of Vitis vinifera or wine. The ability of these compounds to act as radical scavengers was investigated using 1,1 diphenyl-2-picryl-hydrazyl, a stable free radical. Antioxidant activities were assessed by their capacity to prevent Cu2+-induced lipid peroxidation in human low-density lipoprotein.