Ring A-seco mosquito larvicidal limonoids from Turraea wakefieldii

Phytochemistry. 2003 Oct;64(4):817-23. doi: 10.1016/j.phytochem.2003.08.020.

Abstract

Five novel limonoids, 1-5, were isolated from the root bark of Turraea wakefieldii and were characterized as tecleaninoid derivatives. This is the first report of the natural occurrence of tecleanin-type limonoids with a five-membered-ring A-seco structure for which we propose the name neotecleanins. The relative stereochemical structures of compounds 1-5 were established on the basis of NMR spectroscopy. The absolute stereochemical structure of 5 was confirmed by X-ray diffraction methods. In mosquito larvicidal assays, compounds 1, 2 and 4 showed dose-dependent larvicidal activity against larvae of Anopheles gambiae s.s.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anopheles*
  • Biological Assay / methods
  • Crystallography, X-Ray
  • Insecticides / chemistry*
  • Insecticides / isolation & purification
  • Larva
  • Limonins / chemistry*
  • Limonins / isolation & purification
  • Magnetic Resonance Spectroscopy
  • Meliaceae / chemistry*
  • Molecular Structure
  • Plant Bark / chemistry
  • Plant Roots / chemistry
  • Stereoisomerism

Substances

  • Insecticides
  • Limonins