Two new stilbene dimer glucosides from grape (Vitis vinifera) cell cultures

J Nat Prod. 2001 Jan;64(1):136-8. doi: 10.1021/np000426r.

Abstract

Two new stilbene dimer glucosides, resveratrol (E)-dehydrodimer 11-O-beta-D-glucopyranoside (1) and resveratrol (E)-dehydrodimer 11'-O-beta-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 IC(50) values in the range of 5 microM, whereas compound 4 was approximately 10-fold less active.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Cells, Cultured
  • Cyclooxygenase 1
  • Cyclooxygenase 2
  • Cyclooxygenase 2 Inhibitors
  • Cyclooxygenase Inhibitors / chemistry*
  • Cyclooxygenase Inhibitors / isolation & purification
  • Glucosides / chemistry*
  • Glucosides / isolation & purification
  • Isoenzymes / chemistry
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Prostaglandin-Endoperoxide Synthases / chemistry
  • Rosales / chemistry*
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Stilbenes*

Substances

  • Cyclooxygenase 2 Inhibitors
  • Cyclooxygenase Inhibitors
  • Glucosides
  • Isoenzymes
  • Stilbenes
  • resveratrol dehydrodimer 11-O-glucopyranoside
  • Cyclooxygenase 1
  • Cyclooxygenase 2
  • Prostaglandin-Endoperoxide Synthases