Laboratory of Chemistry, National Heart, Lung, and Blood Institute, 20892, Bethesda, Maryland.
J Chem Ecol. 1988 Jan;14(1):35-45. doi: 10.1007/BF01022529.
Novel 2-ethyl-5-alkylpyrrolidines and their corresponding 1-pyrrolines have been identified as poison gland products from an unidentified Australian species ofMonomorium. The major alkaloids present in the venom of this ant aretrans-2-ethyl-5-undecylpyrrolidine andtrans-2-ethyl-5-(12-tridecen-1-yl)pyrrolidine. The position of the double bond in the latter was established from its dimethyl-disulfide adduct after the amine function had been protected, and the stereochemistry of the alkyl groups was determined by direct comparison with synthetic compounds. The corresponding 1-pyrrolines were also detected in varying amounts in this venom. The pyrrolidines and 1-pyrrolines possess considerable insecticidal activity when evaluated against termite workers. The alkaloidal venoms ofMonomorium appear to be an important factor contributing to the success of these small ants both as competitors and as predators.
已从一种未鉴定的澳大利亚弓背蚁属（Monomorium）物种的毒腺中鉴定出新型 2-乙基-5-烷基吡咯烷及其相应的 1-吡咯啉。这种蚂蚁毒液中的主要生物碱为反式-2-乙基-5-十一烷基吡咯烷和反式-2-乙基-5-（12-十三碳烯-1-基）吡咯烷。后者中双键的位置是通过保护胺官能团后其二甲基二硫化物加合物确定的，烷基的立体化学结构通过与合成化合物的直接比较确定。这种毒液中也检测到了不同含量的相应 1-吡咯啉。当对白蚁工蚁进行评估时，吡咯烷和 1-吡咯啉具有相当大的杀虫活性。Monomorium 的生物碱毒液似乎是这些小型蚂蚁作为竞争者和捕食者成功的重要因素。
