Estrogenic/antiestrogenic and scavenging properties of (E)- and (Z)-resveratrol.
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.
Basly
J P
JP
UPRES EA 1085 Biomolécules et cibles cellulaires tumorales, UFR de Pharmacie, Limoges, France. basly@unilim.fr
Marre-Fournier
F
F
Le Bail
J C
JC
Habrioux
G
G
Chulia
A J
AJ
D002455:Cell Division / Q000187:drug effects; D003198:Computer Simulation; D045166:Estradiol Congeners / Q000494:pharmacology*; D004965:Estrogen Antagonists / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000494:pharmacology*; D017930:Genes, Reporter / Q000235:genetics; D006801:Humans; D007501:Iron / Q000378:metabolism; D008156:Luciferases / Q000096:biosynthesis / Q000235:genetics; D010084:Oxidation-Reduction; D011960:Receptors, Estrogen / Q000187:drug effects; D000077185:Resveratrol; D013237:Stereoisomerism; D013267:Stilbenes / Q000494:pharmacology*; D014407:Tumor Cells, Cultured; D014819:Vitellogenins / Q000096:biosynthesis
D045166:Estradiol Congeners; D004965:Estrogen Antagonists; D016166:Free Radical Scavengers; D011960:Receptors, Estrogen; D013267:Stilbenes; D014819:Vitellogenins; D007501:Iron; D008156:Luciferases; D000077185:Resveratrol