A novel lepidopteran sex pheromone produced by females of a Lithosiinae species, Lyclene dharma dharma, in the family of Arctiidae

Biosci Biotechnol Biochem. 2007 Nov;71(11):2860-3. doi: 10.1271/bbb.70551. Epub 2007 Nov 7.

Abstract

Female moths of Lyclene dharma dharma (Arctiidae, Lithosiinae) produced three pheromone components (I-III), which strongly stimulated male antennae. Using GC-MS analysis and chemical derivatizations, the following structures were estimated: 6-methyl-2-octadecanone (I), 14-methyl-2-octadecanone (II), and 6,14-dimethyl-2-octadecanone (III). While the stereochemistry of the chiral centers could not be determined because it was difficult to collect a sufficient amount of the natural pheromone, the plain structures of I and II were confirmed by synthesis of the racemic mixtures starting from diols. These methyl-branched ketones have not been identified as a natural product, indicating that they constitute a new chemical group of lepidopteran female sex pheromones.

MeSH terms

  • Animals
  • Female
  • Gas Chromatography-Mass Spectrometry
  • Ketones / analysis
  • Ketones / chemistry
  • Ketones / metabolism*
  • Molecular Structure
  • Moths / metabolism*
  • Sex Attractants / analysis
  • Sex Attractants / chemistry
  • Sex Attractants / metabolism*

Substances

  • 14-methyl-2-octadecanone
  • 6,14-dimethyl-2-octadecanone
  • 6-methyl-2-octadecanone
  • Ketones
  • Sex Attractants