Six isoflavones, daidzein (40,7,-dihydroxyisoflavone), genistein (40,5,7-trihydroxyisoflavone), genistin (genistein 7-O- b-D-glucopyranoside), isoprunetin (40,7-dihydroxy, 5-metoxyisoflavone), isoprunetin 7-O-b-D-glucopyranoside, iso- prunetin 40,7-di-O-b-D-glucopyranoside and four flavones, luteolin (30,40,5,7-tetrahydroxyflavone), luteolin 7-O-b-D- glucopyranoside, luteolin 40-O-b-D-glucopyranoside, licoflavone C (40,5,7-trihydroxy,8-isoprenylflavone) were purified from Mediterranean plants (Genista morisii and Genista ephedroides) and their estrogenic activity was assessed by a yeast reporter gene assay (Saccharomyces cerevisiae RMY326 ER-ERE). Licoflavone C showed a powerful estrogenic activity at 107 M (0.0338 mg/ml) and it was 47.45% than 108 M 17b-estradiol (0.00272 mg/ml). The estrogenicity of this flavone was found to be comparable to the activity showed by genistein at 106 M (0.27 mg/ml). This study points out that a glucose substituent in flavones and isoflavones modulates the hormone-like activity in a different way. Isoflavone aglycones showed a more estrogenic activity than the corresponding glucosides. Conversely, the glucosidation made estrogenic the flavone luteolin and the position of substitution differently influenced the estrogenic activity of compounds.
Assessment of estrogenic activity of flavonoids from Mediterranean plants using an in vitro short term test
PINTO, BARBARA;PISTELLI, LUISA;
2005-01-01
Abstract
Six isoflavones, daidzein (40,7,-dihydroxyisoflavone), genistein (40,5,7-trihydroxyisoflavone), genistin (genistein 7-O- b-D-glucopyranoside), isoprunetin (40,7-dihydroxy, 5-metoxyisoflavone), isoprunetin 7-O-b-D-glucopyranoside, iso- prunetin 40,7-di-O-b-D-glucopyranoside and four flavones, luteolin (30,40,5,7-tetrahydroxyflavone), luteolin 7-O-b-D- glucopyranoside, luteolin 40-O-b-D-glucopyranoside, licoflavone C (40,5,7-trihydroxy,8-isoprenylflavone) were purified from Mediterranean plants (Genista morisii and Genista ephedroides) and their estrogenic activity was assessed by a yeast reporter gene assay (Saccharomyces cerevisiae RMY326 ER-ERE). Licoflavone C showed a powerful estrogenic activity at 107 M (0.0338 mg/ml) and it was 47.45% than 108 M 17b-estradiol (0.00272 mg/ml). The estrogenicity of this flavone was found to be comparable to the activity showed by genistein at 106 M (0.27 mg/ml). This study points out that a glucose substituent in flavones and isoflavones modulates the hormone-like activity in a different way. Isoflavone aglycones showed a more estrogenic activity than the corresponding glucosides. Conversely, the glucosidation made estrogenic the flavone luteolin and the position of substitution differently influenced the estrogenic activity of compounds.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
