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The Flavonoid Kaempferol Is Responsible for the Majority of Estrogenic Activity in Red Wine

¹ Christian Doppler Laboratory for Receptor Biotechnology, Muthgasse 18, A-1190 Vienna, Austria; ² University of Natural Resources and Applied Life Sciences, Department of Biotechnology, Muthgasse 18, A-1190 Vienna, Austria; ³ Federal College and Research Institute for Viticulture and Pomolgy, A-3400 Klosterneuburg, Austria; and ⁴ University of Natural Resources and Applied Life Sciences, Department of Chemistry, Muthgasse 18, A-1190 Vienna, Austria.

^* Corresponding author (email: alois.jungbauer{at}boku.ac.at; fax: 0043 1 3697615; tel: 0043 1 36006 6226)

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 β (ERβ), with equivalent concentrations ranging from 40 to 140 nmol/L. Estrogenicity was more weakly mediated by estrogen receptor (ER), with equivalent concentrations of ~14 nmol/L and minimal ER transactivation. Kaempferol and apigenin strongly bound to ERβ, with inhibitory concentrations (IC₅₀) of 5.1 x 10^–8 M and 3.8 x 10^–7 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 ERβ (1.0 x 10^–5 M). Most compounds had low affinity to ER, 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-β ligands in red wine, vintners may aim to optimize the polyphenol composition in wines without changing sensory properties.

Key words: apigenin, estrogen receptor, kaempferol, red wine