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Caste-Specific Tyramides from Myrmicine Ants

2010; American Chemical Society; Volume: 73; Issue: 3 Linguagem: Inglês

10.1021/np900697s

1520-6025

Tappey H. Jones, H. Martin Garraffo, Thomas F. Spande, Nirina R. Andriamaharavo, Jeffrey S. T. Gorman, Alexander J. Snyder, Andrew W. Jeter, Juan A. Torres, Roy R. Snelling, John W. Daly,

Plant and animal studies

Analysis of the extracts of male ants of Monomorium minimum and Monomorium ebeninum by GC−MS and GC−FTIR revealed the presence of tyramides 2 and 4c, for which the structures were established by comparison with synthetic samples. These compounds and their analogues 1 and 3 were also found in males of other Monomorium species, males of Myrmicaria opaciventris, and males of several Solenopsis (Diplorhoptrum) species. Vapor-phase FTIR spectra revealed critically important structural clues to two of the tyramides, which had methyl branching in the tyramide acyl moiety. Tyramide 4c exhibited a strong intramolecular amide NH hydrogen bond where an α-keto group was deduced to be present in the acyl moiety and also showed the overlap of this ketone group frequency with that of the amide νC═O. The biological function of these compounds is uncertain; however, their role in ant-mating behavior may be suggested by a large body of evidence.