Novel pyrrolidines in the venom of the ant Monomorium indicum.
New 2,5-dialkylpyrrolidines found in the venom of Monomorium indicum include trans-2-butyl-5-(4-pentenyl)pyrrolidine [1], trans-2-butyl-5-(6-heptenyl)pyrrolidine [4], trans-5-(5-hexenyl)-2-(4-pentenyl)pyrrolidine [6], trans-5-(6-heptenyl)-2-(5-hexenyl)pyrrolidine [8], and trans-5-heptyl-2-hexylpyrrolidine [16], whose structures were confirmed by synthesis. The concomitance of five previously reported trans-2,5-dialkyl-pyrrolidines along with small amounts of the cis isomers and N-methyl analogues makes the venom of M. indicum the most qualitatively diverse blend of alkaloids reported from an ant to date. The toxicities to termites of four of these alkaloids were determined.
Jones
T H
TH
Laboratory of Chemistry, National Heart, Lung, and Blood Institute, Bethesda, Maryland 20892.
Blum
M S
MS
Escoubas
P
P
Musthak Ali
T M
TM
D000818:Animals; D000862:Ant Venoms / Q000032:analysis*; D001180:Arthropod Venoms; D007313:Insecta; D009682:Magnetic Resonance Spectroscopy; D011759:Pyrrolidines / Q000032:analysis / Q000302:isolation & purification* / Q000633:toxicity
D000862:Ant Venoms; D001180:Arthropod Venoms; D011759:Pyrrolidines