8-prenylnaringenin
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IUPAC name
(2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
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| Other names
Hopein; Flavaprenin; Sophoraflavanone B
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3D model (Jmol)
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PubChem CID
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| Properties | |
| C20H20O5 | |
| Molar mass | 340.38 g·mol−1 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
8-Prenylnaringenin (8-PN), also known as flavaprenin, (S)-8-dimethylallylnaringenin, hopein, or sophoraflavanone B, is a prenylflavonoid phytoestrogen. It is reported to be the most estrogenic phytoestrogen known. The compound is equipotent at ERα and ERβ, and acts as a full agonist of ERα. Its effects are similar to those of estradiol, but it is considerably less potent in comparison.
8-PN is found in hops (Humulus lupulus) and in beer, and is responsible for the estrogenic effects of the former. It can be produced from isoxanthohumol in fungal cells cultures, and by flora in the human intestine.
In an in vitro study, 8-PN and its synthesized derivatives of it demonstrated to have anticancer activity.
8-PN was shown to preserve bone density and has been demonstrated to reduce hot flashes. 8-PN also induces the secretion of prolactin, and increases other estrogenic responses. The compound binds to and activates ERα more times than it does to ERβ.
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-PN 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-PN, are common in herbal breast enlargement preparations.
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