Isoflavonoids from Erythrina poeppigiana: Evaluation of Their Binding Affinity for the Estrogen Receptor

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′...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2009-09, Vol.72 (9), p.1603-1607
Main Authors: Djiogue, Sefirin, Halabalaki, Maria, Alexi, Xanthippi, Njamen, Dieudonne, Fomum, Zacharias Tanee, Alexis, Michael N, Skaltsounis, Alexios-Leandros
Format: Article
Language:English
Subjects:
Biological and medical sciences
Bolivia
Erythrina - chemistry
Estrogen Receptor alpha - drug effects
Estrogen Receptor beta - drug effects
General pharmacology
Genistein - pharmacology
Humans
Isoflavones - chemistry
Isoflavones - isolation & purification
Isoflavones - pharmacology
Medical sciences
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Plant Bark - chemistry
Plant Stems - chemistry
Structure-Activity Relationship
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Summary: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 ERα and ERβ was evaluated using a receptor binding assay. While isoprenyl and dimethylpyrano substituents in ring A reduced the affinity of binding to ERβ 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.
ISSN:0163-3864
1520-6025
DOI:10.1021/np900271m