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

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

Date: 1998

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

Publication Series: Scientific Journal (JRNL)

Description: 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

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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.


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