Phytochemicals/8-prenylnaringenin

8-Prenylnaringenin (8-PN) or hopein is a prenylflavonoid found in hops. It is the most estrogenic phytoestrogen known, and its effects are similar to estradiol at a fraction of the potency. There is another compound, 8-isopentenylnaringenin, also known as sophoraflavanone B, from sophora flavescens, that could properly be called 8-prenylnaringenin by scientific naming convention.

8-neopentylnaringenin and 8-n-heptylnaringenin are synthetic forms of 8-Prenylnaringenin. Synthesized derivatives of 8-prenylnaringenin are: 7,4′-di-O-methyl-8-prenylnaringenin; 7-O-pentyl-8-prenylnaringenin; 7,4′-Di-O-allyl-8-prenylnaringenin; 7,4′-Di-O-acetyl-8-prenylnaringenin; and 7,4′-Di-O-palmitoyl-8-prenylnaringenin. 6-prenylnaringenin, xanthohumol, isoxanthohumol, and desmethylxanthomul are precursors to 8-prenylnaringenin.

Properties
In an in vitro study, 8-Prenylnaringenin and its synthesized derivatives of it demonstrated to have anticancer activity. This prenylflavonoid was shown to preserve bone density, in lab studies.

8-Prenylnaringenin has been demonstrated to reduce hot flashes, in a preclinical study. 8-Prenylnaringenin also influences prolactin, and increases other estrogenic responses. This prenylflavonoid interacts with the progesterone receptor, estrogen receptor beta, and estrogen receptor alpha. 8-prenylnaringenin binds to and activates ER-α more times than it does to ER-β in vitro.

This prenylflavanoid has drawn interest in the study of hormone replacement therapy, and it is comparable to selective estrogen-receptor modulators.

In an in vivo study, 8-prenylnaringenin has activated proliferation of mammary cells. At the concentration found in beer, it is unlikely to have an estrogenic effect in breast tissue. Prenylflavonoids from hops, namely 8-prenylnaringenin, are common in herbal breast enlargement preparations.

Luteinizing hormone (LH) and follicle stimulating hormone (FSH) are reduced by 8-prenylnaringenin. 8-Prenylnaringenin adversely affects male sperm. The role 8-prenylnaringenin plays in fertility requires further research.