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J Agric Food Chem. 2009 Apr 22;57(8):3128-33. doi: 10.1021/jf803561y.

Piperideine alkaloids from the poison gland of the red imported fire ant (Hymenoptera: Formicidae).

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Biological Control of Pests Research Unit, Agricultural Research Service, US Department of Agriculture, Stoneville, Mississippi 38776, USA.


The major chemical components in the venom of red imported fire ants, Solenopsis invicta Buren, are 2-methyl-6-alkyl or alkenyl piperidines. After isolating the extracts of poison glands and whole worker bodies with column chromatography, we obtained fractions containing a mixture of six piperideine alkaloids. Reduction of those samples using NaBH(4) in ethanol generated piperidine alkaloids found in the fire ant poison gland, resulting in both the cis- and the trans-piperidine alkaloids. The mass spectra and gas chromatographic behavior of most piperidine alkaloids from fire ant venom have been well-characterized, which significantly facilitated the identification of these piperdeine compounds. On the basis of the mass spectra and profiles of NaBH(4) reduction products, we identified these alkaloids as 2-methyl-6-tridecenyl-6-piperideine, 2-methyl-6-tridecyl-6-piperideine, 2-methyl-6-pentadecenyl-6-piperideine, 2-methyl-6-pentadecyl-6-piperideine, 2-methyl-6-heptadecenyl-6-piperideine, and 2-methyl-6-heptadecyl-6-piperideine. To our knowledge, this is the first time that these piperideine alkaloids have been reported in red imported fire ant poison glands.

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