(5Z,9Z)-3-alkyl-5-methylindolizidines fromSolenopsis (Diplorhoptrum) species |
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| Authors: | Tappey H Jones Robert J Highet Murray S Blum Henry M Fales |
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| Affiliation: | (1) Department of Chemistry, United States Naval Academy, 21402 Annapolis, Maryland;(2) Laboratory of Chemistry, National Heart, Lung, and Blood Institute National Institutes of Health, 20205 Bethesda, Maryland;(3) Department of Entomology, University of Georgia, 30602 Athens, Georgia |
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| Abstract: | The alkaloidal venom components of two species of thief ants,Solenopsis (Diplorhoptrum) species AA andS. (Diplorhoptrum)conjurata have been found to contain (5Z,9Z)-3-hexyl-5-methylindolizidine and a mixture of (5Z,9Z)-3-ethyl-5-methylindolizidine andcis-2-methyl-6-nonyl-piperidine,trans-2-methyl-6-nonylpiperidine,cis-2-methyl-6-undecylpiperidine, and hexadecanoic acid.Monomorium pharaonis was similarly investigated and found to contain the indolizidine and pyrrolidines previously described (Ritter et al., 1977b). Both indolizidines were synthesized along with their stereoisomers and separated by preparative gas chromatography. Spectral studies revealed the stereochemistry to be 5Z,9Z in both cases. The stereochemistry of 2-butyl-5-pentylpyrrolidine inM. phaeronis has also been established. Biosynthetic relationships are discussed. |
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| Keywords: | Ants Solenopsis (Diplorhoptrum) species Monomorium pharaonis Hymenoptera Formicidae 3-alkyl-5-methylindolizidines alkaloids venom components 2 5-dialkylpyrrolidines |
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