Isoflavonoids from Erythrina poeppigiana: evaluation of their binding affinity for the estrogen receptor.

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Djiogue S, Halabalaki M, Alexi X, Njamen D, Fomum ZT, Alexis MN, Skaltsounis AL

Isoflavonoids from Erythrina poeppigiana: evaluation of their binding affinity for the estrogen receptor.

J Nat Prod. 2009 Sep;72(9):1603-7. doi: 10.1021/np900271m.

PubMed ID
19705860 [ View in PubMed
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Abstract

Five new isoflavones, named 5,4'-dihydroxy-7-methoxy-3'-(3-methylbuten-2-yl)isoflavone (1), 5,2',4'-trihydroxy-7-methoxy-5'-(3-methylbuten-2-yl)isoflavone (2), 5,4'-dihydroxy-7-methoxy-3'-(3-methyl-2-hydroxybuten-3-yl)isoflavone (3), 3'-formyl-5,4'-dihydroxy-7-methoxyisoflavone (4), and 5-hydroxy-3''-hydroxy-2'',2''-dimethyldihydropyrano[5'',6'':3',4']isoflavone (5), as well as six known compounds, wighteone (6), 3'-isoprenylgenistein (7), isolupabigenin (8), alpinumisoflavone (9), erypoegin D (10), and crystacarpin (11), were isolated from Erythrina poeppigiana. The structures of the isolated compounds were elucidated on the basis of chemical and spectroscopic analysis. The affinity of these compounds for the estrogen receptors ERalpha and ERbeta was evaluated using a receptor binding assay. While isoprenyl and dimethylpyrano substituents in ring A reduced the affinity of binding to ERbeta ca. 100-fold compared to genistein, the isoprenyl substituent in ring B was better accommodated, allowing 7 to bind with ca. 10-fold lower affinity than genistein.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
EstradiolEstrogen receptor alphaIC 50 (nM)3.2N/AN/ADetails
EstradiolEstrogen receptor betaIC 50 (nM)2.9N/AN/ADetails