Journal of Chemical Ecology

, Volume 44, Issue 5, pp 444–451 | Cite as

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


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.


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



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)


  1. Ali MF, Morgan ED, Detrain C, Attygalle AB (1988) Identification of a component of the trail pheromone of the ant Pheidole pallidula (Hymenoptera: Formicidae). Physiol Entomol 13:257–265CrossRefGoogle Scholar
  2. Attygalle AB, Morgan ED (1984a) Chemicals from the glands of ants. Chem Soc Rev 13:245–278CrossRefGoogle Scholar
  3. Attygalle AB, Morgan ED (1984b) Identification of trail pheromone of the ant Tetramorium caespitum L. (Hymenoptera:Myrmicnae). J Chem Ecol 10:1453–1468Google Scholar
  4. Attygalle AB, Morgan ED (1985) Ant trail pheromones. Adv Insect Physiol 18:1–30CrossRefGoogle Scholar
  5. Biemann K (1962) Mass spectrometry. Organic Chemical Applications, McGraw Hill Book Company, pp 182–183Google Scholar
  6. Blum MS (1970) Chemicals controlling insect behavior: the chemical basis of insect sociality. Academic press, New York and London 61–94Google Scholar
  7. Brophy JJ (1989) Pyrazines obtained from insects: their source, identification, synthesis, and function. In: Atta-ur-Rahmam (ed) studies in natural products chemistry: structure elucidation. Elsevier, Amsterdam, pp 221–273Google Scholar
  8. Cavill GWK, Robertson PL, Brophy JJ, Duke RK, McDonald J, Plant WD (1984) Chemical ecology of the meat ant, Iridomyrmex purpureus sens. strict. Insect Biochem 14:505–513CrossRefGoogle Scholar
  9. Howard DF, Blum MS, Jones TH, Tomalski MD (1982) Behavioral responses to an alkylpyrazine from the mandibular gland of the ant Wasmannia auropunctata. Insect Soc 29:369–374CrossRefGoogle Scholar
  10. Jones TH, Garraffo HM, Blum MS, Everett DM, Hastings H, Ware AB (1998) Elucidation of dimethylalkylpyrazines from the ant Streblognathus aethiopicus by GC-FTIR. J Chem Ecol 24:125–134CrossRefGoogle Scholar
  11. Klein B, Spoerri BE (1951) The action of organolithium compounds on 2,5-dimethylpyrazine. J Am Chem Soc 73:2949–2951CrossRefGoogle Scholar
  12. Larabee FJ, Fisher BL, Schmidt CA, Matos-Maraví P, Janda M, Suarez AV (2016) Molecular phylogenetics and diversification of trap-jaw ants in the genera Anochetus and Odontomachus (Hymenoptera: Formicidae). Mol Phylogenet Evol 103:143–154CrossRefPubMedGoogle Scholar
  13. Lee GE, Shrimp LFI, Weiberth FJ (2010) Improved Chemical Synthesis of diazaindoles by Chichibabin cyclization, International patent Application PCT/US2010/027755, 18 MarchGoogle Scholar
  14. Longhurst C, Baker R, Howse PE, Speed WJ (1978) Alkylpyrazines in ponerine ants: their presence in three genera, and caste specific behavioural responses to them in Odontomachus troglodytes. J Insect Physiol 24:833–837CrossRefGoogle Scholar
  15. Mihara S, Enomoto N (1985) Calculation of retention indices of pyrazines on the basis of molecular structure. J Chromatogr 324:428–430CrossRefGoogle Scholar
  16. Mihara S, Masuda HJ (1987) Correlation between molecular structures and retention indices of pyrazines. J Chromatogr 402:309–317CrossRefGoogle Scholar
  17. Morgan ED (2009) Review article: trail pheromones of ants. Physiol Entomol 34:1–17CrossRefGoogle Scholar
  18. Morgan ED, Jungnickel H, Keegans SJ, Do Nascimento RR, Billen J, Gobin B, Ito F (2003) Comparative survey of abdominal gland secretions of the ant subfamily ponerinae. J Chem Ecol 29:95–114CrossRefPubMedGoogle Scholar
  19. Morgan ED, Nascimento RRD, Keegans SJ, Billen J (1999) Comparative study of mandibular gland secretions of workers of ponerine ants. J Chem Ecol 25:1395–1409CrossRefGoogle Scholar
  20. Napper E, Pickett JA (2008) Alarm pheromones of insects. Encyclopedia of. Entomology:85–95Google Scholar
  21. Sainz-Borgo C, Cabrera A, Hernandez JV (2011) Nestmate recognition in the ant Odontomachus bauri (Hymenoptera: Formicidae). Sociobiology 58:701–718Google Scholar
  22. Showalter DN, Troyer EJ, Aklu M, Jang EB, Siderhurst MS (2010) Alkylpyrazines: alarm pheromone components of the little fire ant, Wasmannia auropunctata (Roger) (Hymenoptera, Formicidae). Insect Soc 57:223–232CrossRefGoogle Scholar
  23. Stanton DT, Jurs PC (1989) Computer-assisted prediction of gas chromatographic retention indices of pyrazines. Anal Chem 61:1328–1332CrossRefGoogle Scholar
  24. Tentschert J, Bestmann HJ, Hölldobler B, Heinze J (2000) 2,3-Dimethyl-5-(2-methylpropyl)pyrazine, a trail pheromone component of Eutetramorium mocquerysi Emery (1899) (Hymenoptera: Formicidae). Naturwissenschaften 87:377–380CrossRefPubMedGoogle Scholar
  25. Vander Meer RK, Preston CA, Choi MY (2010) Isolation of a pyrazine alarm pheromone component from the fire ant, Solenopsis invicta. J Chem Ecol 36:163–170CrossRefPubMedGoogle Scholar
  26. Wheeler JW, Blum MS (1973) Alkylpyrazine alarm pheromones in ponerine ants. Science 182:501–503CrossRefPubMedGoogle Scholar

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

Personalised recommendations