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Isolation and Structure Elucidation of an Isoflavone and a Sesterterpenoic Acid from Henriettella fascicularis

Calderón, Angela I.
Terreaux, Christian
Schenk, Kurt
Pattison, Phil
Burdette, Joanna E.
Pezzuto, John M.
Gupta, Mahabir P.
Published in Journal of Natural Products. 2002, vol. 65, no. 12, p. 1749 - 1753
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.
Keywords estrogen-receptorflavonoidslignansspectra
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