Estrogenic/antiestrogenic and scavenging properties of (E)- and (Z)-resveratrol

Life Sci. 2000 Jan 21;66(9):769-77. doi: 10.1016/s0024-3205(99)00650-5.

Abstract

Resveratrol, natural compound found in grapes and wine, has been reported to have a variety of health benefit properties. Based on the structural similarity to the synthetic estrogen diethylstilbestrol, we investigated estrogenic/antiestrogenic effects on human breast cancer cell lines, MCF-7 and MVLN, and scavenging properties using DPPH of both (E)- and (Z)-isomers. Both isomers increased the in vitro growth of MCF-7 cell lines at medium concentrations (10 and 25 microM) whereas the low concentrations (0.1 and 1 microM) had no effect and the high concentration (50 microM) decreased the cell growth and was cytotoxic. The 25 microM (E)-isomer alone was able to reduced the proliferation induced by the estradiol. Low concentrations of (E)- and (Z)-resveratrol (0.1 and 1 microM) and medium concentration 10 microM (Z)-resveratrol did not interfere with the estrogen receptor. In contrast, medium concentrations of (E)-resveratrol (10 and 25 microM) and (Z)-resveratrol (25 microM) functioned as superagonists of estradiol. Whatever the model used, MCF-7 or MVLN cell lines, (Z)-resveratrol was less effective than (E)-resveratrol. Extinction of DPPH and Fe(III) reduction experiments showed that both isomers of resveratrol could act as free radicals scavengers or pro-oxidant compounds. The properties of low concentrations of resveratrol raise the possibility that structure-function studies could lead to the development of more selective estrogen receptor agonists and antagonists, which could be useful as a therapeutic agent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Division / drug effects
  • Computer Simulation
  • Estradiol Congeners / pharmacology*
  • Estrogen Antagonists / pharmacology*
  • Free Radical Scavengers / pharmacology*
  • Genes, Reporter / genetics
  • Humans
  • Iron / metabolism
  • Luciferases / biosynthesis
  • Luciferases / genetics
  • Oxidation-Reduction
  • Receptors, Estrogen / drug effects
  • Resveratrol
  • Stereoisomerism
  • Stilbenes / pharmacology*
  • Tumor Cells, Cultured
  • Vitellogenins / biosynthesis

Substances

  • Estradiol Congeners
  • Estrogen Antagonists
  • Free Radical Scavengers
  • Receptors, Estrogen
  • Stilbenes
  • Vitellogenins
  • Iron
  • Luciferases
  • Resveratrol