Journal
TOXICON
Volume 53, Issue 5, Pages 469-478Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.toxicon.2008.12.019
Keywords
Fire ant; Solenopsis richteri; Venom; Solenopsins; Alkaloid
Categories
Funding
- Alabama Fire Ant Management
- Auburn University Biogrants
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Dialkylpiperidines are characteristic of fire ants in the genus Solenopsis (Hymenoptera: Formicidae). Workers of the black imported fire ant, S. richteri produce cis and trans stereoisomers; of 2,6-dialkylpiperidines with the trans isomer predominating. We used silica gel short column chromatography to separate both stereoisomers (cis and trans) of S. richteri venom alkaloids and coupled gas chromatography mass spectrometry (GC-MS) to identify novel minor components. The identities of various peaks in GC-MS analyses of the venom fractions were based on relative retention times and mass spectral data. CC profiles verified the presence of both cis and trans stereoisomers of C-15:1 and C-15 in S. richteri. The CC trace of the cis stereoisomers of S. richteri alkaloids was presented for the first time. In addition to the previously described components of S. richteri venom, seven novel 2,6-dialkyl-Delta(1,2)-piperideines and 2,6-dialkyl-Delta(1,6)-piperideines were detected. The chemical identities of these minor components were determined by comparing with fragmentations of known compounds. Possible biosynthetic pathways for the production of cis and trans solenopsins by S. richteri are discussed. Published by Elsevier Ltd.
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