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  • Title: SAR Study on Estrogen Receptor α/β Activity of (Iso)flavonoids: Importance of Prenylation, C-Ring (Un)Saturation, and Hydroxyl Substituents.
    Author: Mbachu OC, Howell C, Simmler C, Malca Garcia GR, Skowron KJ, Dong H, Ellis SG, Hitzman RT, Hajirahimkhan A, Chen SN, Nikolic D, Moore TW, Vollmer G, Pauli GF, Bolton JL, Dietz BM.
    Journal: J Agric Food Chem; 2020 Sep 30; 68(39):10651-10663. PubMed ID: 32945668.
    Abstract:
    Many botanicals used for women's health contain estrogenic (iso)flavonoids. The literature suggests that estrogen receptor beta (ERβ) activity can counterbalance estrogen receptor alpha (ERα)-mediated proliferation, thus providing a better safety profile. A structure-activity relationship study of (iso)flavonoids was conducted to identify ERβ-preferential structures, overall estrogenic activity, and ER subtype estrogenic activity of botanicals containing these (iso)flavonoids. Results showed that flavonoids with prenylation on C8 position increased estrogenic activity. C8-prenylated flavonoids with C2-C3 unsaturation resulted in increased ERβ potency and selectivity [e.g., 8-prenylapigenin (8-PA), EC50 (ERβ): 0.0035 ± 0.00040 μM], whereas 4'-methoxy or C3 hydroxy groups reduced activity [e.g., icaritin, EC50 (ERβ): 1.7 ± 0.70 μM]. However, nonprenylated and C2-C3 unsaturated isoflavonoids showed increased ERβ estrogenic activity [e.g., genistein, EC50 (ERβ): 0.0022 ± 0.0004 μM]. Licorice (Glycyrrhiza inflata, [EC50 (ERα): 1.1 ± 0.20; (ERβ): 0.60 ± 0.20 μg/mL], containing 8-PA, and red clover [EC50 (ERα): 1.8 ± 0.20; (ERβ): 0.45 ± 0.10 μg/mL], with genistein, showed ERβ-preferential activity as opposed to hops [EC50 (ERα): 0.030 ± 0.010; (ERβ): 0.50 ± 0.050 μg/mL] and Epimedium sagittatum [EC50 (ERα): 3.2 ± 0.20; (ERβ): 2.5 ± 0.090 μg/mL], containing 8-prenylnaringenin and icaritin, respectively. Botanicals with ERβ-preferential flavonoids could plausibly contribute to ERβ-protective benefits in menopausal women.
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