Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 12, Issue 6, Pages 1559-1567Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2003.11.035
Keywords
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Funding
- NCI NIH HHS [5R01 CA19118, 5R01 CA77355] Funding Source: Medline
- NIDDK NIH HHS [5R37 DK15556] Funding Source: Medline
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Equol is a metabolite produced in vivo from the soy phytoestrogen daidzein by the action of gut microflora. It is known to be estrogenic, so human exposure to equol could have significant biological effects. Equol is a chiral molecule that can exist as the enantiomers R-equol and S-equol. To study the biological activity of racemic (+/-)-equol, as well as that of its pure enantiomers, we developed an efficient and convenient method to prepare (+/-)-equol from available isollavanoid precursors. Furthermore, we optimized a method to separate the enantiomers of equol by chiral HPLC, and we studied for the first time, the activities of the enantiomers on the two estrogen receptors, ERalpha and ERbeta. In binding assays, S-equol has a high binding affinity, preferential for ERbeta (K-i[ERbeta] = 16 nM; beta/alpha = 13 fold), that is comparable to that of genistein (K-i[ERbeta] = 6.7 nM; beta/alpha= 16), whereas R-equol binds more weakly and with a preference for ERalpha (K-i[ERalpha] = 50 nM; beta/alpha = 0.29). All equol isomers have higher affinity for both ERs than does the biosynthetic precursor daidzein. The availability an the in vitro characterization of the equol enantiomers should enable their biological effects to be studied in detail. (C) 2004 Elsevier Ltd. All rights reserved.
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