Prenylated anthronoid antioxidants from the stem bark of Harungana madagascariensis

Phytochemistry. 2005 May;66(10):1174-9. doi: 10.1016/j.phytochem.2005.03.022.

Abstract

Two new prenylated anthronoids, harunmadagascarins A and B, were isolated from the stem bark of Harungana madagascariensis along with six known compounds including two anthronoids: harunganol B and harungin anthrone, one benzophenone: methyl 3-formyl-2,4-dihydroxy-6-methyl benzoate and three pentacyclic triterpenes: friedelin, lupeol and betulinic acid. Harunmadagascarins A and B were characterized as 8,9-dihydroxy-4,4-bis-(3,3-dimethylallyl)-6-methyl-2,3-(2,2-dimethylpyrano)anthrone and 8,9-dihydroxy-4,4,5-tris-(3,3-dimethylallyl)-6-methyl-2,3-(2,2-dimethylpyrano)anthrone, respectively. The structures of these secondary metabolites were determined by spectroscopic means and comparison with the published data. Methyl 3-formyl-2,4-dihydroxy-6-methyl benzoate was isolated for the first time from a plant. Harunmadagascarins A and B, harunganol B and harungin anthrone exhibited significant antioxidant activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthracenes / chemistry*
  • Antioxidants / chemistry*
  • Clusiaceae / chemistry*
  • Free Radical Scavengers / chemistry
  • Molecular Structure
  • Plant Bark / chemistry*
  • Plant Stems / chemistry

Substances

  • Anthracenes
  • Antioxidants
  • Free Radical Scavengers