SHORT COMMUNICATION

Naturwissenschaften

, Volume 96, Issue 12, pp 1443-1449

First online:

Orange/lemon-scented beetles: opposite enantiomers of limonene as major constituents in the defensive secretion of related carabids

  • Athula B. AttygalleAffiliated withDepartment of Chemistry, Chemical Biology and Biomedical Engineering, Stevens Institute of Technology Email author 
  • , Xiaogang WuAffiliated withDepartment of Chemistry, Chemical Biology and Biomedical Engineering, Stevens Institute of Technology
  • , David R. MaddisonAffiliated withDepartment of Entomology, University of Arizona
  • , Kipling W. WillAffiliated withDepartment of Environmental Science, Policy and Management, Division of Organisms and Environment, University of California

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Abstract

The major constituent in the pygidial gland defensive fluid of the carabid beetle Ardistomis schaumii is (R)-(+)-limonene, whereas that of Semiardistomis puncticollis is (S)-(−)-limonene. This was an unanticipated result, since it is not very common to find the opposite enantiomers of the same compound among the secondary metabolites of related species. Moreover, the glandular liquid of A. schaumii contains 1,8-cineole, and that of S. puncticollis has β-pinene, β-phellandrene, sabinene, and p-cymene. Of about 500 carabid species that have been chemically investigated, this is the first report of the presence of such complex mixtures of monoterpenes in their defensive secretions.

Keywords

Carabid beetle β-pinene p-cymene Terpenes Semiardistomis puncticollis Ardistomis schaumii Limonene