Re-investigation of venom chemistry of Solenopsis fire ants. I. Identification of novel alkaloids in S. richteri

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. GC profiles verified the presence of both cis and trans stereoisomers of C_15:1 and C₁₅ in S. richteri. The GC 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-Δ^1,2-piperideines and 2,6-dialkyl-Δ^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.