3-Hexyl-5-Methylindolizidine Isomers from Thief Ants, Solenopsis (Diplorhoptrum) Species |
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| Authors: | J S T Gorman T H Jones T F Spande R R Snelling J A Torres H M Garraffo |
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| Affiliation: | (1) Department of Chemistry, Virginia Military Institute, Lexington, Virginia, 24450;(2) Laboratory of Bioorganic Chemistry, NIDDK, NIH, Bethesda, Maryland, 20892-0820;(3) os Angeles County Museum of Natural History, 900 Exposition Blvd., Los Angeles, California, 9007;(4) University of Puerto Rico, P.O. Box 23360, San Juan, Puerto Rico, 00931;(5) IITF, United States Forest Service, P.O. Box 25000, Rio Piedras, Puerto Rico, 00928 |
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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 (1c) or (5Z,9E)-3-hexyl-5-methylindolizidine (1d) 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. |
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| Keywords: | Venom alkaloids Solenopsis (Diplorhoptrum) indolizidine chemotaxonomy |
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