Stylopsal: the first identified female-produced sex pheromone of strepsiptera

J Chem Ecol. 2012 Dec;38(12):1483-91. doi: 10.1007/s10886-012-0214-7. Epub 2012 Nov 11.

Abstract

A female-produced sex pheromone of Stylops muelleri was identified as an unusually branched saturated aldehyde (9R)-3,5-syn-3,5,9-trimethyldodecanal. We named it stylopsal. Its structure was established by using mass spectrometry, infrared spectroscopy, and organic synthesis of candidate compounds. The synthetic standard of (9R)-3,5-syn-3,5,9-trimethyldodecanal gave identical chromatographic and mass spectrometric data as the natural pheromone and also was active in electroantennographic and behavioral assays. The female fat body lipids contained the corresponding fatty acid, indicating a possible link between lipid metabolism and the pheromone biosynthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / analysis*
  • Aldehydes / chemical synthesis
  • Aldehydes / pharmacology
  • Animals
  • Fat Body / chemistry
  • Female
  • Gas Chromatography-Mass Spectrometry
  • Insecta / chemistry
  • Insecta / physiology*
  • Male
  • Sex Attractants / chemistry*
  • Sexual Behavior, Animal / drug effects
  • Sexual Behavior, Animal / physiology
  • Spectrophotometry, Infrared
  • Stereoisomerism

Substances

  • 3,5,9-trimethyldodecanal
  • Aldehydes
  • Sex Attractants