Laboratory of Chemistry, National Heart, Lung, and Blood Institute, 20892, Bethesda, Maryland.
J Chem Ecol. 1988 Dec;14(12):2197-212. doi: 10.1007/BF01014025.
A comparative analysis of the venom alkaloids produced by ants in the genusMonomorium (= Chelaner) collected on North Island and South Island, New Zealand, has been undertaken. All of the ants producetrans-2, 5-dialkylpyrrolidines along with 3,5-dialkylpyrrolizidines. The structures and sterochemistry of the novel alkaloidstrans-2-butyl-5-(8-nonenyl) pyrrolidine, (5E,8Z)-3,5-di(5-hexenyl)pyrrolizidine, and (5Z,8E)-3-methyl-5-(8-nonenyl)pyrrolizidine were established by unambiguous synthesis. The geographic distribution and the chemotaxonomic significance of the alkaloids produced by these ants are discussed.
对在新西兰北岛和南岛采集的单枝蚁属(= Chelaner)蚂蚁所产生的毒液生物碱进行了比较分析。所有的蚂蚁都产生反式-2,5-二烷基吡咯烷以及 3,5-二烷基吡咯里啶。通过明确的合成,确定了新型生物碱反式-2-丁基-5-(8-壬烯基)吡咯烷、(5E,8Z)-3,5-二(5-己烯基)吡咯里啶和(5Z,8E)-3-甲基-5-(8-壬烯基)吡咯里啶的结构和立体化学。讨论了这些蚂蚁产生的生物碱的地理分布和化学生态学意义。