Journal of Chemical Ecology

, Volume 28, Issue 12, pp 2527–2539

Semiochemicals of the Scarabaeinae. VII: Identification and Synthesis of EAD-Active Constituents of Abdominal Sex Attracting Secretion of the Male Dung Beetle, Kheper subaeneus

  • B. V. Burger
  • W. G. B. Petersen
  • W. G. Weber
  • Z. M. Munro
Article

DOI: 10.1023/A:1021440220329

Cite this article as:
Burger, B.V., Petersen, W.G.B., Weber, W.G. et al. J Chem Ecol (2002) 28: 2527. doi:10.1023/A:1021440220329

Abstract

Using gas chromatography with flame ionization detection (FID) and electroantennographic detection (EAD) in parallel, butanoic acid, skatole, and (E)-2,6-dimethyl-6-octen-2-ol were identified as constituents of the abdominal sex-attracting secretion of the male dung beetle, Kheper subaeneus, which reproducibly elicited EAD responses in male and female antennae. This is the first report of the occurrence of (E)-2,6-dimethyl-6-octen-2-ol as a natural product, for which the name (E)-subaeneol is proposed. In some experiments, a few other constituents of the secretion also gave reproducible responses in specific male and female antennae but did not elicit responses when the analyses were repeated with other antennae. The major volatile constituent of the secretion, identified as (S)-(+)-2,6-dimethyl-5-heptenoic acid, is one of these EAD-active compounds. Both this compound and (E)-2,6-dimethyl-6-octen-2-ol were synthesized from authentic starting materials for comparison with the natural products.

ScarabaeinaeKheper subaeneusdung beetlesex attractantinsect semiochemicalselectroantennographyterpenessemiochemical synthesis

Copyright information

© Plenum Publishing Corporation 2002

Authors and Affiliations

  • B. V. Burger
    • 1
  • W. G. B. Petersen
    • 1
  • W. G. Weber
    • 1
  • Z. M. Munro
    • 1
  1. 1.Laboratory for Ecological Chemistry, Department of ChemistryUniversity of StellenboschStellenboschSouth Africa