Anti-mitotic properties of resveratrol analog (Z)-3,5,4'-trimethoxystilbene

Issue title: Free Radicals in Biology and Medicine: From Inflammation to Biotechnology

Article type: Research Article

Authors: Chabert, Philippe | Fougerousse, André | Brouillard, Raymond

Affiliations: Laboratoire de Chimie des Polyphénols, Université Strasbourg I, Faculté de Chimie, CNRS, UMR 7177, 1, rue Blaise Pascal, 67000 Strasbourg, France

Note: [] Corresponding author. Tel.: + 33 390 241 342; Fax: +33 390 241 341; E-mail: brouil@chimie.u-strasbg.fr

Abstract: (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 μM 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.

Keywords: Polyphenol, resveratrol, anti-mitotic, Caco-2 cells, colon cancer, tubulin

Journal: BioFactors, vol. 27, no. 1-4, pp. 37-46, 2006