The endocrine activities of 8-prenylnaringenin and related hop (Humulus lupulus L.) flavonoids.
The female flowers of the hop plant have long been used as a preservative and a flavoring agent in beer, but they are now being included in some herbal preparations for women for "breast enhancement." This study investigated the relative estrogenic, androgenic and progestogenic activities of the known phytoestrogen, 8-prenylnaringenin, and structurally related hop flavonoids. 6-Prenylnaringenin, 6,8-diprenylnaringenin and 8-geranylnaringenin exhibited some estrogenicity, but their potency was less than 1% of that of 8-prenylnaringenin. 8-Prenylnaringenin alone competed strongly with 17ss-estradiol for binding to both the alpha- and ss-estrogen receptors. None of the compounds (xanthohumol, isoxanthohumol, 8-prenyl-naringenin, 6-prenylnaringenin, 3'-geranylchalconaringenin, 6-geranylnaringenin, 8-geranylnaringenin, 4'-O:-methyl-3'-prenylchalconaringenin and 6,8-diprenylnaringenin) nor polyphenolic hop extracts showed progestogenic or androgenic bioactivity. These results indicate that the endocrine properties of hops and hop products are due to the very high estrogenic activity of 8-prenylnaringenin and concern must be expressed about the unrestricted use of hops in herbal preparations for women.
Milligan
S R
SR
Endocrinology and Reproduction Research Group, School of Biomedical Sciences, King's College, London SE1 1UL, United Kingdom.
Kalita
J C
JC
Pocock
V
V
Van De Kauter
V
V
Stevens
J F
JF
Deinzer
M L
ML
Rong
H
H
De Keukeleire
D
D
D000728:Androgens / Q000096:biosynthesis; D001667:Binding, Competitive / Q000187:drug effects; D004702:Endocrine Glands / Q000187:drug effects* / Q000378:metabolism; D047628:Estrogen Receptor alpha; D047629:Estrogen Receptor beta; D004967:Estrogens / Q000096:biosynthesis; D004968:Estrogens, Non-Steroidal / Q000378:metabolism / Q000494:pharmacology*; D005260:Female; D044950:Flavanones; D005419:Flavonoids / Q000378:metabolism / Q000494:pharmacology*; D006801:Humans; D007529:Isoflavones; D010636:Phenols / Q000494:pharmacology; D048789:Phytoestrogens; D028321:Plant Preparations; D010946:Plants, Medicinal / Q000737:chemistry*; D011372:Progestins / Q000096:biosynthesis; D011960:Receptors, Estrogen / Q000378:metabolism; D012441:Saccharomyces cerevisiae / Q000378:metabolism
C119737:8-prenylnaringenin; D000728:Androgens; D047628:Estrogen Receptor alpha; D047629:Estrogen Receptor beta; D004967:Estrogens; D004968:Estrogens, Non-Steroidal; D044950:Flavanones; D005419:Flavonoids; D007529:Isoflavones; D010636:Phenols; D048789:Phytoestrogens; D028321:Plant Preparations; D011372:Progestins; D011960:Receptors, Estrogen