8-prenylnaringenin

8-prenylnaringenin is a prenylflavonoid phytoestrogen found primarily in hops (Humulus lupulus) and beer[4][15]. It is among the most estrogenic phytoestrogens known, acting as a potent agonist of the estrogen receptors, especially ERα, and to a lesser extent ERβ[1][4][10][13]. Its activity is 50–1500 times greater than genistein or daidzein but is markedly less potent than estradiol[1][4]. 8-prenylnaringenin exhibits both estrogenic and antigonadotropic activities, suppressing luteinizing hormone (LH) and follicle-stimulating hormone (FSH) levels in humans[4][7]. It has demonstrated effects similar to estradiol, including preserving bone density, reducing hot flashes, inducing prolactin secretion, and increasing other estrogenic responses[4]. Beyond endocrine effects, it displays anticancer properties in vitro, such as inhibition of proliferation and induction of apoptosis in various cancer cell lines, likely associated with inhibition of voltage-gated Kv1.3 potassium channels[1][4]. It can also enhance GABA_A receptor activity[4]. The compound is being studied as a possible alternative to hormone replacement therapy (HRT) and for management of menopause-related symptoms[1][7][9].

Other names

5,7,4'-trihydroxy-8-prenylflavanoneisobavachinflavapreninhopeinsophoraflavanone B(S)-8-dimethylallylnaringenin(+/-)-8-prenylnaringenin