Production of (5R,6S)-6-acetoxy-5-hexadecanolide, the mosquito oviposition pheromone, from the seed oil of the summer cypress plant, Kochia scoparia (Chenopodiaceae)

J Agric Food Chem. 1999 Aug;47(8):3411-5. doi: 10.1021/jf990294b.

Abstract

The oviposition pheromone for the pathogen-vectoring mosquitoes in the genus Culex (Diptera: Culicidae), that is, (5R, 6S)-6-acetoxy-5-hexadecanolide, is efficiently synthesized, in admixture with the inactive (5S,6R) enantiomer ( approximately 33% w/w), from the fixed oil extracted from the seeds of the summer cypress plant, Kochia scoparia (Chenopodiaceae), cultivated on an industrial scale. Oviposition bioassays using gravid females of Culex quinquefasciatus, a vector of filariasis in human beings, showed that the product was attractive, with activity comparable to that of a pure synthetic sample containing the same amount of the active enantiomer. Production of the pheromone in the form of a biologically active crude material via a cheap and renewable plant suitable for development as a new industrial crop provides the basis for control of Cx. quinquefasciatus and other congeneric vectors of pathogens in resource-poor areas of the world.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biological Assay
  • Chenopodiaceae*
  • Culex / physiology*
  • Female
  • Humans
  • Insect Vectors
  • Molecular Structure
  • Oviposition / drug effects*
  • Pheromones / biosynthesis*
  • Pheromones / isolation & purification
  • Pheromones / pharmacology
  • Plant Oils / chemistry*
  • Pyrones / isolation & purification
  • Pyrones / metabolism*
  • Pyrones / pharmacology

Substances

  • Pheromones
  • Plant Oils
  • Pyrones
  • 6-acetoxy-5-hexadecanolide