Solenopsis punctaticeps

The venom of the fire ant, Solenopsis punctaticeps, contains several 2,5-dialkyl-pyrrolidines and -pyrrolines their structures have been settled by combined g.c-m.s., and confirmed by syntheses employing the Hofmann-Loffler reaction on the corresponding primary amines.7 A new synthesis of 2,5-dialkyl-pyrrolidines via lithiated iV-nitrosopyrrolidine and two stages of alkylation, followed by removal of the nitroso-group, should be applicable to the synthesis of the venom components. The major products are trans in stereochemistry.8... 

Pedder DJ, Fales HM, Jaouni T, Blum M, MacConneU J, Crewe RM. Constituents of the venom of a south aMcan lire ant Solenopsis punctaticeps) 2,5-dialkylpyirolidines and pyrrolines, identification and synthesis. Tetrahedron 1976 32(19) 2275-2279. 

Both possible isomers of the 2,5-dialkyl-1-pyrrolines have been identified in the venoms of Solenopsis and Monomorium species. These compounds generally accompany the corresponding dialkylpyrrolidines as venom constituents. The venom of 3. punctaticeps, an African species, contains both 61- and -pyrrolines (VII) (j3) as do the venoms of three North American Monomorium species (12 ). The latter dialkylpyrrolines (VIII) are distinguished by the presence of two terminally unsaturated side chains. The pyrrolines in the venom of M. latinode are distinctive in constituting the only 5-pyrrolines (IX) in ant venoms that are not accompanied by the 1-pyrrolines (6). 

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