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Chemoecology

, Volume 29, Issue 4, pp 171–178 | Cite as

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

  • Sihang Xu
  • Ramu Errabeli
  • Kipling Will
  • Elizabeth Arias
  • Athula B. AttygalleEmail author
Original Article

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.

Keywords

Defensive secretion Methacrylic acid Tiglic acid Ceroglossus buqueti and Ceroglossus magellanicus Ceroglossus chilensis 3-Methyl-1-(methylthio)-2-butene Methyl prenyl sulfide Sulfur-containing natural products 

Notes

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).

Supplementary material

49_2019_286_MOESM1_ESM.docx (210 kb)
Supplementary material 1 (DOCX 210 kb)

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Copyright information

© Springer Nature Switzerland AG 2019

Authors and Affiliations

  1. 1.Department of Chemistry and Chemical Biology, Center for Mass SpectrometryStevens Institute of TechnologyHobokenUSA
  2. 2.Department of Environmental Science, Policy and ManagementUniversity of CaliforniaBerkeleyUSA
  3. 3.Essig Museum of EntomologyUniversity of CaliforniaBerkeleyUSA

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