Isolation and structure elucidation of an isoflavone and a sesterterpenoic acid from Henriettella fascicularis.

Article Details

Citation

Calderon AI, Terreaux C, Schenk K, Pattison P, Burdette JE, Pezzuto JM, Gupta MP, Hostettmann K

Isolation and structure elucidation of an isoflavone and a sesterterpenoic acid from Henriettella fascicularis.

J Nat Prod. 2002 Dec;65(12):1749-53.

PubMed ID
12502307 [ View in PubMed
]
Abstract

A new isoflavone, 4',5,7-trihydroxy-6,8-dimethylisoflavone (1), and a new sesterterpenoic acid (2), together with five known compounds, lichexanthone (3), (-)-pinoresinol (4), betulinic acid, palmitic acid, and beta-sitosterol, were isolated from a dichloromethane extract of the branches of Henriettella fascicularis. Their structures were established by extensive spectroscopic methods. An attempt to determine the absolute stereochemistry of (2E,6S)-6-[(1R,5Z,3aS,9R,10Z,12aR)-1,2,3,3a,4,7,8,9,12,12a-decahydro-9-hydroxy-3a ,6,10-trimethylcyclopentanocycloundecen-1-yl]-2-methylhept-2-enoic acid (2) was performed by single-crystal X-ray analysis, using Cu Kalpha radiation. Compound 1 showed significant competitive binding to estrogen receptor beta and moderate antiestrogenic activity with cultured Ishikawa cells.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
GenisteinEstrogen receptor alphaIC 50 (nM)300N/AN/ADetails
GenisteinEstrogen receptor betaIC 50 (nM)18N/AN/ADetails