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J Chem Ecol

Title:		Alkyl-Dimethylpyrazines in Mandibular Gland Secretions of Four Odontomachus Ant Species (Formicidae: Ponerinae)
Author(s):		Xu S; Errabeli R; Feener DH; Noble K; Attygalle AB;
Address:		"Center for Mass Spectrometry, Department of Biomedical Engineering, Chemistry, and Biological Sciences, Stevens Institute of Technology, Hoboken, NJ, 07030, USA. Department of Biology, University of Utah, Salt Lake City, UT, 84112, USA. Center for Mass Spectrometry, Department of Biomedical Engineering, Chemistry, and Biological Sciences, Stevens Institute of Technology, Hoboken, NJ, 07030, USA. aattygal@stevens.edu"
Journal Title:		J Chem Ecol
Year:		2018
Volume:		20180328
Issue:		5
Page Number:		444 - 451
DOI:		10.1007/s10886-018-0948-y
ISSN/ISBN:		1573-1561 (Electronic) 0098-0331 (Linking)
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:		Alkylation Animals Ants/*chemistry/physiology Gas Chromatography-Mass Spectrometry Isomerism Methylation Pheromones/*analysis/metabolism Pyrazines/*analysis/metabolism Species Specificity Alkylpyrazines Odontomachus bauri Odontomachus chelifer Odontomachu;
Notes:		"MedlineXu, Sihang Errabeli, Ramu Feener, Donald H Noble, Katherine Attygalle, Athula B eng IOS 1052372/National Science Foundation/ IOS 10-52352/National Science Foundation/ 2018/03/29 J Chem Ecol. 2018 May; 44(5):444-451. doi: 10.1007/s10886-018-0948-y. Epub 2018 Mar 28"