Monomorium pyrrolidine venom alkaloids

Several species pertaining to the sub-family Myrmicinae (e.g., Solenopsis spp., Monomorium spp.) are characterized by a venom rich in dialkylated saturated nitrogen heterocycles (e.g., piperidine, pyrrolidine, indolizidine, pyrrolizidine). Exhaustive lists of these alkaloids have already been published [114-116]. Since then, only a few more of these alkaloids have been reported from a few further species. 

The disubstituted pyrrolidines and piperidines have been demonstrated to be excellent repellents for ants under field conditions. Workers of Monomorium pharaonis effectively repel other species of ants with venom droplets which accumulate on the tip of the sting (37), a strategy that is used with equal success by workers of North American Monomorium species ( 38.) and the European thief ant, Solenopsis fugax (37). The venom of the latter species contains a single alkaloid, trans-2-butyl-5-heptylpyrrolidine (I, m=3, n=6) (1 ), and the... 

Following the initial discovery of alkyl-substituted piperidines in Solenopsis venom, a very large number of structurally related alkaloids were identified in the venom from ants of the subfamilies Myrmicinae and Pseudomyrmicinae, all of which share a carbon skeleton based on a single unbranched chain. Analyses of ants from the genera Solenopsis, Monomorium, and Diplorhoptrum revealed 2,5-dialkylated pyrrolidines,... 

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