RT Journal Article
SR Electronic
T1 The Flavonoid Kaempferol Is Responsible for the Majority of Estrogenic Activity in Red Wine
JF American Journal of Enology and Viticulture
JO Am J Enol Vitic.
FD American Society for Enology and Viticulture
SP 223
OP 232
DO 10.5344/ajev.2009.60.2.223
VO 60
IS 2
A1 Zoechling, Alfred
A1 Reiter, Evelyne
A1 Eder, Reinhard
A1 Wendelin, Silvia
A1 Liebner, Falk
A1 Jungbauer, Alois
YR 2009
UL http://www.ajevonline.org/content/60/2/223.abstract
AB 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 α (ERα), with equivalent concentrations of ~14 nmol/L and minimal ERα transactivation. Kaempferol and apigenin strongly bound to ERβ, with inhibitory concentrations (IC50) of 5.1 × 10−8 M and 3.8 × 10−7 M, respectively. trans-Resveratrol and quercetin were moderate binders, with IC50 of 4.0 × 10−6 M and 1.1 × 10−6 M, respectively; naringenin and myricetin bound with low affinity ERβ (1.0 × 10−5 M). Most compounds had low affinity to ERα, with IC50 greater than 1 × 10−5 M; the exceptions were kaempferol and apigenin, with IC50 of 8.2 × 10−6 M and 2.3 × 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.