Limonoids from Aphanamixis polystachya and their antifeedant activity

J Nat Prod. 2014 Mar 28;77(3):472-82. doi: 10.1021/np400678h. Epub 2013 Nov 20.

Abstract

Eight new aphanamixoid-type aphanamixoids (C-J, 1-8) and six new prieurianin-type limonoids, aphanamixoids K-P (9-14), along with 10 known terpenoids were isolated from Aphanamixis polystachya, and their structures were established by spectroscopic data analysis. Among the new limonoids, 13 compounds exhibited antifeedant activity against the generalist Helicoverpa armigera, a plant-feeding insect, at various concentration levels. In particular, compounds 1, 4, and 5 showed potent activities with EC50 values of 0.017, 0.008, and 0.012 μmol/cm(2), respectively. On the basis of a preliminary structure-activity relationship analysis, some potential active sites in the aphanamixoid-type limonoid molecules are proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Algorithms
  • Animals
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Drug Screening Assays, Antitumor
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology*
  • Feeding Behavior / drug effects*
  • HL-60 Cells
  • Humans
  • Larva / drug effects
  • Lepidoptera / drug effects
  • Limonins / chemistry
  • Limonins / isolation & purification*
  • Limonins / pharmacology*
  • Meliaceae / chemistry*
  • Molecular Structure
  • Moths / drug effects
  • Nuclear Magnetic Resonance, Biomolecular
  • Spodoptera / physiology
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents, Phytogenic
  • Drugs, Chinese Herbal
  • Limonins
  • prieurianin