Alkyl-Dimethylpyrazines in Mandibular Gland Secretions of Four Odontomachus Ant Species (Formicidae: Ponerinae)

  • Sihang Xu
  • Ramu Errabeli
  • Donald H. Feener
  • Katherine Noble
  • Athula B. Attygalle
Article
  • 47 Downloads

Abstract

Ponerine ants are known to contain mixtures of pyrazines in their mandibular glands. We analyzed the mandibular gland contents of four ponerine species (Odontomachus chelifer, O. erythrocephalus, O. ruginodis, and O. bauri) by gas chromatography coupled with mass spectrometry, and found that each species contains specific mixtures of trisubstituted alkylpyrazines among other volatiles. Attempts to identify alkylpyrazines solely by mass spectral interpretation is unrealistic because spectra of positional isomers are indistinguishable. To avoid misidentifications, we synthesized a large number of reference compounds and compared their mass spectral and gas chromatographic properties with those present in the Odontomachus species under investigation. Most of the compounds identified were 2-alkyl-3,5-dimethylpyrazines. Interestingly, when the third substituent was an isopentyl group, the two methyl groups were found to be located at the 2 and 5 ring positions. Using our data, we recognized several misidentifications in previous publications.

Keywords

Alkylpyrazines Pheromones Retention indices Odontomachus bauri Odontomachus ruginodis Odontomachus chelifer Odontomachus erythrocephalus 

Notes

Acknowledgements

This work was supported by NSF grants to ABA (IOS 1052372) and DHF (IOS 10-52352). We thank Wittko Francke for the gift of 2,5-dimethyl-3-(1-methylbutyl)pyrazine, 2,3-dimethyl-5-(2’-methylbutyl)pyrazine, and 2,5-dimethyl-3-(2’-methylbutyl)pyrazine.

Supplementary material

10886_2018_948_MOESM1_ESM.docx (4.2 mb)
ESM 1 (DOCX 4.17 mb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Center for Mass Spectrometry, Department of Biomedical Engineering, Chemistry, and Biological SciencesStevens Institute of TechnologyHobokenUSA
  2. 2.Department of BiologyUniversity of UtahSalt Lake CityUSA

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