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

J Nat Prod. 2002 Dec;65(12):1749-53. doi: 10.1021/np0201164.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaline Phosphatase / metabolism
  • Binding Sites
  • Cell Line / drug effects
  • Crystallography, X-Ray
  • Endometrium / drug effects
  • Estrogen Antagonists / chemistry
  • Estrogen Antagonists / isolation & purification*
  • Estrogen Antagonists / pharmacology
  • Estrogen Receptor Modulators / chemistry
  • Estrogen Receptor Modulators / isolation & purification*
  • Estrogen Receptor Modulators / pharmacology
  • Female
  • Furans*
  • Humans
  • Isoflavones / chemistry
  • Isoflavones / isolation & purification*
  • Isoflavones / pharmacology
  • Lignans / chemistry
  • Lignans / isolation & purification
  • Melastomataceae / chemistry*
  • Methylation
  • Molecular Conformation
  • Molecular Structure
  • Palmitic Acid / chemistry
  • Palmitic Acid / isolation & purification
  • Panama
  • Phytosterols / chemistry
  • Phytosterols / isolation & purification*
  • Phytosterols / pharmacology
  • Plant Shoots / chemistry
  • Plants, Medicinal / chemistry*
  • Sitosterols / chemistry
  • Sitosterols / isolation & purification
  • Stereoisomerism
  • Terpenes / chemistry
  • Terpenes / isolation & purification*
  • Terpenes / pharmacology

Substances

  • (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
  • 4',5,7-trihydroxy-6,8-dimethylisoflavone
  • Estrogen Antagonists
  • Estrogen Receptor Modulators
  • Furans
  • Isoflavones
  • Lignans
  • Phytosterols
  • Sitosterols
  • Terpenes
  • Palmitic Acid
  • gamma-sitosterol
  • Alkaline Phosphatase
  • pinoresinol