Anti-mitotic properties of resveratrol analog (Z)-3,5,4'-trimethoxystilbene.
(Z)-3,5,4'-Trimethoxystilbene is a natural polyphenol present in five different plants, Virola cuspidata, Virola elongata, Centipeda minima, Schoenus nigricans and Rheum undulatum. This molecule was prepared in a three-step sequence in good overall yield. The isomerisation from the (E)- to (Z)-isomer is performed using UV irradiation. Biological investigations were conducted on a human colon cancer cell line (Caco-2) with anti-mitotic activities. Growth was completely arrested at an added 0.4 microM level of (Z)-3,5,4'-trimethoxystilbene. This agent is 100-fold more active than resveratrol or (E)-3,5,4'-trihydroxystilbene, and the mechanism of this process involves an inhibition of tubulin polymerisation in a dose dependent manner.
Chabert
Philippe
P
Laboratoire de Chimie des Polyphénols, Université Strasbourg I, Faculté de Chimie, CNRS, UMR 7177, 1 rue Blaise Pascal, 67000 Strasbourg, France.
Fougerousse
André
A
Brouillard
Raymond
R
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000494:pharmacology; D018938:Caco-2 Cells; D002453:Cell Cycle / Q000187:drug effects; D049109:Cell Proliferation / Q000187:drug effects*; D003110:Colonic Neoplasms / Q000378:metabolism / Q000473:pathology; D004305:Dose-Response Relationship, Drug; D004587:Electrophoresis, Agar Gel; D005434:Flow Cytometry; D006801:Humans; D008938:Mitosis / Q000187:drug effects*; D000077185:Resveratrol; D013237:Stereoisomerism; D013267:Stilbenes / Q000737:chemistry / Q000494:pharmacology*; D014404:Tubulin / Q000378:metabolism; D050257:Tubulin Modulators / Q000737:chemistry / Q000494:pharmacology
C497286:3,4',5-trimethoxystilbene; D000972:Antineoplastic Agents, Phytogenic; D013267:Stilbenes; D014404:Tubulin; D050257:Tubulin Modulators; D000077185:Resveratrol