An unusual homoisoflavanone and a structurally-related dihydrochalcone from Polygonum ferrugineum (Polygonaceae)

Phytochemistry. 2006 Oct;67(19):2152-8. doi: 10.1016/j.phytochem.2006.06.018. Epub 2006 Aug 1.

Abstract

The homoisoflavanone 5,7-dihydroxy-6-methoxy-3-(9-hydroxy-phenylmethyl)-chroman-4-one (1) and its structurally related 2',4',6'-trihydroxy-3'-methoxy-alpha-hydroxymethyl-beta-hydroxy-dihydrochalcone (2) along with the known pashanone (3), flavokawin B (4) and cardamonin or alpinetin chalcone (5) pinostrobin (6) and 5,8-dimethoxy-7-hydroxychroman-4-one (7) were isolated from dry leaves of Polygonum ferrugineum (Polygonaceae). To our knowledge, this is the first report of the isolation of a homoisoflavanone from the Polygonum genus and the Polygonaceae family, and could be an important chemotaxonomic finding. In addition, the pattern of substitution of this homoisoflavanone is different from others previously reported.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chalcones / chemistry*
  • Chalcones / isolation & purification
  • Chromones / chemistry*
  • Chromones / isolation & purification*
  • Isoflavones / chemistry*
  • Isoflavones / isolation & purification
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular / methods
  • Polygonum / chemistry*

Substances

  • 2',4',6'-trihydroxy-3'-methoxy-alpha-hydroxymethyl-beta-hydroxy-dihydrochalcone
  • 5,7-dihydroxy-6-methoxy-3-(9-hydroxy-phenylmethyl)-chroman-4-one
  • Chalcones
  • Chromones
  • Isoflavones
  • dihydrochalcone
  • cardamonin