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3-Methyl-1-(methylthio)-2-butene: a component in the foul-smelling defensive secretion of two Ceroglossus species (Coleoptera: Carabidae)

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Abstract

A sulfur-containing compound causes the foul smell of the defensive pygidial gland fluid of Ceroglossus buqueti Laporte and Ceroglossus magellanicus Gehin. This compound was identified as 3-methyl-1-(methylthio)-2-butene by a comparison of its mass spectrum, and chromatographic properties with those of a chemically synthesized standard. Although a few sulfur compounds are known from insect secretions, this sulfur-bearing isoprene derivative has not been characterized previously from any arthropod source. Additional components in the defensive section include acetic, propanoic, isobutyric, butanoic, methacrylic, ethacrylic, tiglic and benzoic acids, and 11-tricosene. Samples prepared from specimens of Ceroglossus chilensis Eschscholtz showed methacrylic, ethacrylic, and other acids. However, 3-methyl-1-(methylthio)-2-butene was not detected in the defensive fluid of C. chilensis.

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Acknowledgements

We thank Pablo Wagner from Flor del Lago for his assistance with Ceroglossus specimen collections. We acknowledge financial support from the Natural Science Foundation (NSF) Grants 1556898 (ABA) and 1556957 (KW).

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Authors and Affiliations

  1. Department of Chemistry and Chemical Biology, Center for Mass Spectrometry, Stevens Institute of Technology, Hoboken, NJ, 07030, USA

    Sihang Xu, Ramu Errabeli & Athula B. Attygalle

  2. Department of Environmental Science, Policy and Management, University of California, Berkeley, CA, 94720, USA

    Kipling Will

  3. Essig Museum of Entomology, University of California, Berkeley, CA, 94720, USA

    Elizabeth Arias

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  1. Sihang Xu
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  2. Ramu Errabeli
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Correspondence to Athula B. Attygalle.

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Communicated by Günther Raspotnig.

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Xu, S., Errabeli, R., Will, K. et al. 3-Methyl-1-(methylthio)-2-butene: a component in the foul-smelling defensive secretion of two Ceroglossus species (Coleoptera: Carabidae). Chemoecology 29, 171–178 (2019). https://doi.org/10.1007/s00049-019-00286-0

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