3-Hexyl-5-Methylindolizidine isomers from thief ants Solenopsis (Diplorhoptrum) species

J.S.T. Gorman; T.H. Jones; T.F. Spande; R.R. Snelling; J.A. Torres; H.M. Garraffo

Treesearch

3-Hexyl-5-Methylindolizidine isomers from thief ants Solenopsis (Diplorhoptrum) species

Formally Refereed

Authors:

J.S.T. Gorman, T.H. Jones, T.F. Spande, R.R. Snelling, J.A. Torres, H.M. Garraffo

Year:

1998

Type:

Scientific Journal

Station:

International Institute of Tropical Forestry

Source:

Journal of Chemical Ecology. 24(5):933-943

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Abstract

The venom alkaloids from the workers of nine collections of Solenopsis (Diplorhoptrum) from California contain either (5E,9E)-3-hexyl-5- methylindolizidine (Ic) or (SZ,9E)-3-hexyl-5-methylindolizidine (Id) along with cis-2-methyl-6-nonylpiperidine. The structures of these compounds were determined from their mass spectra and by comparison of their GC-FTIR spectra with those of a synthetic mixture. In view of the facts that a third diastereomer of 3-hexyl-5-methylindolizidine had been reported in previous collections of Solenopsis (Diplorhoptrum) queens from Puerto Rico, and that indolizidines along with other ant venom alkaloids are sequestered by amphibians, the determination of species in this difficult group of ants is significant. In particular, the chemotaxonomic value of the stereochemistry of these venom alkaloids is discussed.

Keywords

Venom, alkaloids, Solenopsis (Diplorhoptrum), indolizidine, chemotaxonomy

Citation

Gorman, J.S.T.; Jones, T.H.; Spande, T.F.; Snelling, R.R.; Torres, J.A.; Garraffo, H.M. 1998. 3-Hexyl-5-Methylindolizidine isomers from thief ants Solenopsis (Diplorhoptrum) species. Journal of Chemical Ecology. 24(5):933-943.