Aphanamixoid A, a potent defensive limonoid, with a new carbon skeleton from Aphanamixis polystachya

Org Lett. 2012 May 18;14(10):2524-7. doi: 10.1021/ol3008149. Epub 2012 Apr 27.

Abstract

Aphanamixoid A (1), a limonoid with a new carbon skeleton, along with its biogenetically related limonoid aphanamixoid B (2), was isolated from the leaves and twigs of Aphanamixis polystachya . Their structures with the absolute stereochemistry were determined by spectroscopic analysis, X-ray crystallography and computational methods. The significant antifeedant activity of 1 against the generalist plant-feeding insect Helicoverpa armigera (EC50 = 0.015 μmol/cm(2)) suggested it may be a potent defensive component of A. polystachya.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Crystallography, X-Ray
  • Feeding Behavior / drug effects
  • Larva / drug effects
  • Lepidoptera / drug effects
  • Limonins / chemistry
  • Limonins / isolation & purification*
  • Limonins / pharmacology*
  • Meliaceae / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Plant Leaves / chemistry
  • Plant Stems / chemistry
  • Spodoptera / drug effects

Substances

  • Limonins
  • aphanamixoid A