Department of Chemistry, United States Naval Academy, 21402, Annapolis, Maryland.
J Chem Ecol. 1984 Aug;10(8):1233-49. doi: 10.1007/BF00988551.
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.
已发现两种盗蚁（Solenopsis（Diplorhoptrum）species AA 和 S.（Diplorhoptrum）conjurata）的生物碱毒液成分含有（5Z，9Z）-3-己基-5-甲基吲哚里西啶和（5Z，9Z）-3-乙基-5-甲基吲哚里西啶与顺式-2-甲基-6-壬基哌啶、反式-2-甲基-6-壬基哌啶、顺式-2-甲基-6-十一烷基哌啶和十六烷酸的混合物。同样对法老蚁（Monomorium pharaonis）进行了研究，发现含有先前描述的吲哚里西啶和吡咯烷（Ritter 等人，1977b）。两种吲哚里西啶都与它们的立体异构体一起合成，并通过制备气相色谱法分离。光谱研究表明在这两种情况下立体化学均为 5Z，9Z。法老蚁（M. phaeronis）中 2-丁基-5-戊基吡咯烷的立体化学也已确定。讨论了生物合成关系。
