Nutrients 2010, 2(3), 340-354; doi:10.3390/nu2030340
Communication

Comparative Effects of R- and S-equol and Implication of Transactivation Functions (AF-1 and AF-2) in Estrogen Receptor-Induced Transcriptional Activity

1 ENITA de Bordeaux, Unité Micronutriments Reproduction Santé, 1 Cours du Général de Gaulle, CS 40201, F-33175 Gradignan cedex, France 2 CNRS UMR 6026, 35042, Equipe \"Récepteur des œstrogènes et destinée cellulaire\", Rennes cedex, France
* Author to whom correspondence should be addressed.
Received: 4 January 2010; in revised form: 20 February 2010 / Accepted: 25 February 2010 / Published: 15 March 2010
(This article belongs to the Special Issue Food and Function 2009)
PDF Full-text Download PDF Full-Text [396 KB, uploaded 15 March 2010 09:51 CET]
Abstract: Equol, one of the main metabolites of daidzein, is a chiral compound with pleiotropic effects on cellular signaling. This property may induce activation/inhibition of the estrogen receptors (ER) a or b, and therefore, explain the beneficial/deleterious effects of equol on estrogen-dependent diseases. With its asymmetric centre at position C-3, equol can exist in two enantiomeric forms (R- and S-equol). To elucidate the yet unclear mechanisms of ER activation/inhibition by equol, we performed a comprehensive analysis of ERa and ERb transactivation by racemic equol, as well as by enantiomerically pure forms. Racemic equol was prepared by catalytic hydrogenation from daidzein and separated into enantiomers by chiral HPLC. The configuration assignment was performed by optical rotatory power measurements. The ER-induced transactivation by R- and S-equol (0.1–10 µM) and 17b-estradiol (E2, 10 nM) was studied using transient transfections of ERa and ERb in CHO, HepG2 and HeLa cell lines. R- and S-equol induce ER transactivation in an opposite fashion according to the cellular context. R-equol and S-equol are more potent in inducing ERa in an AF-2 and AF-1 permissive cell line, respectively. Involvement of ERa transactivation functions (AF-1 and AF-2) in these effects has been examined. Both AF-1 and AF-2 are involved in racemic equol, R-equol and S-equol induced ERa transcriptional activity. These results could be of interest to find a specific ligand modulating ER transactivation and could contribute to explaining the diversity of equol actions in vivo.
Keywords: equol; enantiomeric forms; estrogen receptor; transactivation function; phytoestrogens

Article Statistics

Load and display the download statistics.

Citations to this Article

Cite This Article

MDPI and ACS Style

Shinkaruk, S.; Carreau, C.; Flouriot, G.; Bennetau-Pelissero, C.; Potier, M. Comparative Effects of R- and S-equol and Implication of Transactivation Functions (AF-1 and AF-2) in Estrogen Receptor-Induced Transcriptional Activity. Nutrients 2010, 2, 340-354.

AMA Style

Shinkaruk S, Carreau C, Flouriot G, Bennetau-Pelissero C, Potier M. Comparative Effects of R- and S-equol and Implication of Transactivation Functions (AF-1 and AF-2) in Estrogen Receptor-Induced Transcriptional Activity. Nutrients. 2010; 2(3):340-354.

Chicago/Turabian Style

Shinkaruk, Svitlana; Carreau, Charlotte; Flouriot, Gilles; Bennetau-Pelissero, Catherine; Potier, Mylène. 2010. "Comparative Effects of R- and S-equol and Implication of Transactivation Functions (AF-1 and AF-2) in Estrogen Receptor-Induced Transcriptional Activity." Nutrients 2, no. 3: 340-354.

Nutrients EISSN 2072-6643 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert