Estrogenic activity of the phytoestrogens naringenin, 6-(1,1-dimethylallyl)naringenin and 8-prenylnaringenin.
Chemically synthesized naringenin derivatives, identical to natural occurring compounds, were tested for their estrogenic activity using two independent estrogen screening assays. Using a yeast based estrogen receptor assay, strong estrogenic activities were demonstrated for 6-(1,1-dimethylallyl)naringenin and 8-prenylnaringenin, while the parent compound naringenin did not show recognizable estrogenic activity. In MVLN cells, a bioluminescent MCF-7-derived cell line, the estrogenic activity of 8-prenylnaringenin and 6-(1,1-dimethylallyl)naringenin was detected at concentrations of 10(-6) M and 5 x 10(-6) M respectively. Naringenin demonstrated estrogenic activity but only at a concentration of 10(-5) M. These estrogenic effects are mediated by the ER, as the antiestrogen 4-hydroxytamoxifen inhibited these activities. In summary, this study provides the further confirmation that 8-prenylnaringenin demonstrates high estrogenic activity, and demonstrated for the first time for 6-(1,1-dimethylallyl)naringenin a reasonable high estrogenic activity, while naringenin exhibit low or no estrogenic activity.
Zierau
Oliver
O
Gester
Sven
S
Schwab
Pia
P
Metz
Peter
P
Kolba
Susanne
S
Wulf
Marina
M
Vollmer
Günter
G
D004305:Dose-Response Relationship, Drug; D045166:Estradiol Congeners / Q000494:pharmacology; D004965:Estrogen Antagonists / Q000494:pharmacology; D004968:Estrogens, Non-Steroidal / Q000494:pharmacology*; D044950:Flavanones; D005419:Flavonoids / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D007529:Isoflavones; D015394:Molecular Structure; D048789:Phytoestrogens; D028321:Plant Preparations; D011960:Receptors, Estrogen / Q000187:drug effects*; D013629:Tamoxifen / Q000031:analogs & derivatives* / Q000494:pharmacology; D014407:Tumor Cells, Cultured
C462031:6-(1,1-dimethylallyl)naringenin; C119737:8-prenylnaringenin; D045166:Estradiol Congeners; D004965:Estrogen Antagonists; D004968:Estrogens, Non-Steroidal; D044950:Flavanones; D005419:Flavonoids; D007529:Isoflavones; D048789:Phytoestrogens; D028321:Plant Preparations; D011960:Receptors, Estrogen; D013629:Tamoxifen; C016601:afimoxifene; C005273:naringenin