Homoisoflavanones from Disporopsis aspera

Phytochemistry. 2006 Oct;67(19):2159-63. doi: 10.1016/j.phytochem.2006.06.021. Epub 2006 Aug 8.

Abstract

From cytotoxic extracts of the roots of Disporopsis aspera Engl. (Liliaceae) a homoisoflavanone, disporopsin (3-(2',4'-dihydroxy-benzyl)-5,7-dihydroxy-chroman-4-one) (1) and three rare methyl-homoisoflavanones, 3-(4'-hydroxy-benzyl)-5,7-dihydroxy-6-methyl-chroman-4-one (2), 3-(4'-hydroxy-benzyl)-5,7-dihydroxy-6,8-dimethyl-chroman-4-one (3) and 3-(4'-hydroxy-benzyl)-5,7-dihydroxy-6-methyl-8-methoxy-chroman-4- one (4) along with five other known compounds, N-trans-feruloyl tyramine (5), adenine (6), 5-(hydroxymethyl)-2-furfural (7), beta-sitosterol (8) and beta-sitosteryl glucopyranoside (9) were isolated. The structures of compounds 1-2 were elucidated by spectral data (1, 2-D NMR and EIMS). The four homoisoflavanones (1-4) were found to be cytotoxic against a series of human cancer cell lines (HCT15, T24S, MCF7, Bowes, A549 and K562) with IC(50) ranging from 15 to 200 microM. Possible biosynthesis routes for homoisoflavonoids (1-4) are discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Chromones / chemistry*
  • Chromones / isolation & purification
  • Chromones / pharmacology
  • Humans
  • Inhibitory Concentration 50
  • Isoflavones / chemistry*
  • Isoflavones / isolation & purification
  • Isoflavones / pharmacology
  • K562 Cells
  • Liliaceae / chemistry*
  • Magnetic Resonance Spectroscopy / methods
  • Molecular Structure
  • Spectrometry, Mass, Electrospray Ionization / methods

Substances

  • (3-(2',4'-dihydroxy-benzyl)-5,7-dihydroxy-chroman-4-one)
  • Chromones
  • Isoflavones