Estradiol-antagonistic activity of phenolic compounds from leguminous plants.
Natural flavonoids are currently receiving much attention because of their estrogenic and antiestrogenic properties. Six isoflavones (isoprunetin, isoprunetin 7-O-beta-D-glucopyranoside, isoprunetin 4',7-di-O-beta-D-glucopyranoside, genistein, genistein 7-O-beta-D-glucopyranoside, daidzein), four flavones (luteolin, luteolin 7-O-beta-D-glucopyranoside, luteolin 4'-O-beta-D-glucopyranoside, licoflavone C), isolated from Genista morisii and G. ephedroides (two Leguminosae plants of the Mediterranean area) together with two structurally related pterocarpans, bitucarpin A and erybraedyn C, isolated from Bituminaria bituminosa (Leguminosae), were tested for the antagonist activity by a yeast based estrogen receptor assay (Saccharomyces cerevisiae RMY326 ER-ERE). Most compounds inhibited the estradiol-induced transcriptional activity in a concentration dependent manner. In particular, for the flavone luteolin 77% inhibition of the induced beta-galactosidase activity was observed. Interestingly, licoflavone C exhibited a dose-dependent antagonistic activity at concentrations up to 10(-4) M, but stimulated beta-galactosidase expression at higher concentrations resulting in a U-shaped-like dose-response curve.
Pinto
B
B
Dipartimento di Patologia Sperimentale, Biotecnologie Mediche, Infettivologia ed Epidemiologia, University of Pisa, Pisa, Italy. b.pinto@med.unipi.it
Bertoli
A
A
Noccioli
C
C
Garritano
S
S
Reali
D
D
Pistelli
L
L
D004958:Estradiol / Q000819:agonists; D004965:Estrogen Antagonists / Q000737:chemistry / Q000494:pharmacology*; D007887:Fabaceae / Q000737:chemistry*; D047309:Flavones / Q000737:chemistry / Q000494:pharmacology*; D039761:Genista / Q000737:chemistry; D007529:Isoflavones / Q000737:chemistry / Q000494:pharmacology*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D036343:Pterocarpans; D012441:Saccharomyces cerevisiae / Q000187:drug effects / Q000235:genetics; D013629:Tamoxifen / Q000031:analogs & derivatives / Q000494:pharmacology; D001616:beta-Galactosidase / Q000187:drug effects
D004965:Estrogen Antagonists; D047309:Flavones; D007529:Isoflavones; D010936:Plant Extracts; D036343:Pterocarpans; C488768:bitucarpin A; C488769:erybraedin C; D013629:Tamoxifen; C016601:afimoxifene; D004958:Estradiol; D001616:beta-Galactosidase