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Zoechling, A; Reiter, E; Eder, R; Wendelin, S; Liebner, F; Jungbauer, A.
(2009): The Flavonoid Kaempferol Is Responsible for the Majority of Estrogenic Activity in Red Wine
AMER J ENOL VITICULT. 2009; 60(2): 223-232.

Abstract:: The preventive effect of moderate red wine consumption on cardiovascular and hormone-related diseases and the estrogenic activity of red wines have been attributed to resveratrol. In the present study, we wished to determine which polyphenols in red wine have a high affinity for estrogen receptors (ER). The estrogenicity of the red wines, assessed with ligand binding and yeast transactivation assays, was primarily mediated by estrogen receptor beta (ER beta), with equivalent concentrations ranging from 40 to 140 nmol/L. Estrogenicity was more weakly mediated by estrogen receptor alpha (ER alpha), with equivalent concentrations of similar to 14 nmol/L and minimal ER alpha transactivation. Kaempferol and apigenin strongly bound to ER beta, with inhibitory concentrations (IC50) of 5.1 x 10(-8) M and 3.8 x 10(-1) M, respectively. trans-Resveratrol and quercetin were moderate binders, with IC50 of 4.0 x 10(-6) M and 1.1 x 10(-6) M, respectively; naringenin and myricetin bound with low affinity ER beta (1.0 x 10(-5) M). Most compounds had low affinity to ER alpha, with IC50 greater than 1 x 10(-5) M; the exceptions were kaempferol and apigenin, with IC50 of 8.2 x 10-6 M and 2.3 x 10-6 M, respectively. In this study of eight wines, only 2% of the estrogenic activity was due to trans-resveratrol, thus suggesting revision of the hypothesis that the estrogenicity of red wines is due to trans-resveratrol. In light of the possible positive health effects of ER-beta ligands in red wine, vintners may aim to optimize the polyphenol composition in wines without changing sensory properties.
Authors BOKU Wien:: Jungbauer Alois; Liebner Falk
Find related publications in this database (Keywords): apigenin; estrogen receptor; kaempferol; red wine