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

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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.

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Acknowledgements

The authors wish to thank Theodore Kheel and Stevens Institute of Technology for their generous financial support. In addition, we thank the Puntacana Center for Sustainability and Biodiversity for logistical help, Aman Gill, UC, Berkeley, for assistance with handling and care of the beetle cultures, and Wendy Moore, University of Arizona, Tucson, AZ for providing specimens of Ardistomis. This research was funded (in part) by the USDA-CSREES in partnership with the California State Agricultural Experiment Station, as well as NSF grant DEB-9981935 to DRM.

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Authors and Affiliations

  1. Department of Chemistry, Chemical Biology and Biomedical Engineering, Stevens Institute of Technology, Hoboken, NJ, 07030, USA

    Athula B. Attygalle & Xiaogang Wu

  2. Department of Entomology, University of Arizona, Tucson, AZ, 85721, USA

    David R. Maddison

  3. Department of Environmental Science, Policy and Management, Division of Organisms and Environment, University of California, Berkeley, CA, 94720, USA

    Kipling W. Will

Authors
  1. Athula B. Attygalle
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  2. Xiaogang Wu
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  3. David R. Maddison
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  4. Kipling W. Will
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Correspondence to Athula B. Attygalle.

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Supplementary Figure 1

Semiardistomis puncticollis, a lemon-scented beetle (total body length, 6.25 mm) (JPG 192 kb)

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Attygalle, A.B., Wu, X., Maddison, D.R. et al. Orange/lemon-scented beetles: opposite enantiomers of limonene as major constituents in the defensive secretion of related carabids. Naturwissenschaften 96, 1443–1449 (2009). https://doi.org/10.1007/s00114-009-0596-8

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