Piperideine Alkaloids from the Poison Gland of the Red Imported Fire Ant (Hymenoptera: Formicidae)

Abstract

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.

Workers and alate queens of Solenopsis geminata share qualitatively similar but quantitatively different venom alkaloid chemistry

“…Brand et al (1972) first reported the identification of piperideine 1,2 -C11 from S. xyloni venom. Recently, a number of studies have confirmed the presence of two series of piperideines including 1,6 -C11 and 1,2 -C11 in workers and alate queens of S. richteri, S. invicta, and their hybrid (Chen and Fadamiro, 2009a,b;Chen et al, 2009Chen et al, , 2010aChen et al, ,b, 2012. Piperideine 1,2 -C11 has been hypothesized to act as an intermediate in the interconversion of cis and trans ring isomers (Brand et al, 1972).…”

Response of Workers to Polyoxyethylene Tridecyl Ether Surfactants in Relation to Hydrophilic-lipophilic Balance

“…Colonies were maintained in the same condition as described by Chen and his colleagues [20]. All colonies of S. invicta were free of Kneallhazia solenopsae, a microsporidian pathogen.…”

Insect natural products and processes: New treatments for human disease

“…Copyright, 2010, American Chemical Society. Leclercq et al, 1994;Arbiser et al, 2007;Chen et al, 2009a a Many other components, such as the amines, histamine, dopamine, and small peptides and enzymes, are not included here as they are either not unique to venom or knowledge of their activities and properties is limited. See: Palma (2006), Monteiro et al (2009), Matysiak et al (2011 and references in Table 2 The major proteins in royal jelly, and to a lesser extent in honey, the apalbumins, have also been shown to act as decoys to block the PA-IIL lectin of P. aeruginosa which is responsible for biofilm formation and the adhesion of bacteria to animal cells (Lerrer et al, 2007).…”

“…The venom of most ants, in contrast to the proteinaceous venoms of other Hymenopterans, is composed mainly of alkaloids (Chen et al, 2009a). In the red imported fire ant, Solenopsis invicta, six of these piperideine alkaloids have been characterised.…”