Three isoflavanones with cannabinoid-like moieties from Desmodium canum

Phytochemistry. 2003 Sep;64(2):599-602. doi: 10.1016/s0031-9422(03)00201-2.

Abstract

Three further derivatives of 5,7,2',4'-tetrahydroxy-6-methyl isoflavanone have been isolated from the root extract of Desmodium canum and assigned the structures 2,3-dihydro-5,7-dihydroxy-6-methyl-3-(1a,2,3,3a,8b,8c-hexahydro-6-hydroxy-1,1,3a-trimethyl-1H-4-oxabenzo[f]cyclobut[c,d]inden-7-yl)-4H-1-benzopyran-4-one (1) 2,3-dihydro-5,7-dihydroxy-6-methyl-3-(6a,7,8,10a-tetrahydro-3-hydroxy-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-2-yl)-4H-1-benzopyran-4-one (2) 2,3-dihydro-5,7-dihydroxy-6-methyl-3-(3-hydroxy-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-2-yl) 4H-1-benzopyran-4-one (3). The three compounds and the previously isolated chromene 4 all derive from the geranylated precursor 5 by a series of cannabinoid-like oxidative rearrangements.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cannabinoids / chemistry*
  • Fabaceae / chemistry*
  • Isoflavones / chemistry*
  • Isoflavones / isolation & purification*
  • Magnetic Resonance Spectroscopy
  • Plant Extracts / chemistry
  • Plant Roots / chemistry

Substances

  • Cannabinoids
  • Isoflavones
  • Plant Extracts
  • isoflavanone