Jones Tappey H, Voegtle Heather L, Miras Heather M, Weatherford Robert G, Spande Thomas F, Garraffo H Martin, Daly John W, Davidson Diane W, Snelling Roy R
Department of Chemistry, Virginia Military Institute, Lexington, Virginia 24450, USA.
J Nat Prod. 2007 Feb;70(2):160-8. doi: 10.1021/np068034t. Epub 2007 Jan 23.
Analysis of the extracts of the ant Myrmicaria melanogaster from Brunei in the Indonesian archipelago by GC-MS and GC-IR revealed the presence of five new alkaloids, identified as (9Z)-3-propylindolizidine (1), cis- and trans-2-butyl-5-propylpyrrolidine (2 and 3, respectively), (10E)-3-butyllehmizidine (7), and (5Z,8Z,9Z)-3-butyl-5-propyl-8-hydroxyindolizidine (10a), whose structures were established by comparison with synthetic samples. In addition the monoterpene hydrocarbons beta-pinene, myrcene, and limonene were detected along with all four isomers of 3-butyl-5-methylindolizidine (4a-d), cis- and trans-2-butyl-5-(4-pentenyl)pyrrolidine (5a and 5b), trans-2-butyl-5-pentylpyrrolidine (6), (5Z,9Z)-3-butyl-5-propylindolizidine (8), and (5Z,9E)-3-butyl-5-propylindolizidine (9), alkaloids well known from ants and frogs, whose structures were established on the basis of published spectra or comparison with authentic samples. This study utilized vapor-phase infrared analysis for the assignment of stereochemistry using Bohlmann bands for the bicyclic alkaloids and, in the case of 10a, the detection of an intramolecular hydrogen bond. A biogenetic relationship between the mono- and bicyclic ring systems is proposed.
通过气相色谱 - 质谱联用（GC - MS）和气相色谱 - 红外光谱联用（GC - IR）对来自印度尼西亚群岛文莱的黑腹蚁（Myrmicaria melanogaster）提取物进行分析，结果显示存在五种新生物碱，分别鉴定为（9Z）-3 - 丙基中氮茚（1）、顺式和反式 - 2 - 丁基 - 5 - 丙基吡咯烷（分别为2和3）、（10E）-3 - 丁基列米齐定（7）以及（5Z，8Z，9Z）-3 - 丁基 - 5 - 丙基 - 8 - 羟基中氮茚（10a），其结构通过与合成样品对比得以确定。此外，还检测到单萜烃类β - 蒎烯、月桂烯和柠檬烯，以及3 - 丁基 - 5 - 甲基中氮茚的所有四种异构体（4a - d）、顺式和反式 - 2 - 丁基 - 5 - （4 - 戊烯基）吡咯烷（5a和5b）、反式 - 2 - 丁基 - 5 - 戊基吡咯烷（6）、（5Z，9Z）-3 - 丁基 - 5 - 丙基中氮茚（8）和（5Z，9E）-3 - 丁基 - 5 - 丙基中氮茚（9），这些生物碱在蚂蚁和青蛙中较为常见，其结构根据已发表的光谱或与标准样品对比得以确定。本研究利用气相红外分析，通过双环生物碱的博尔曼带确定立体化学，并在10a的情况下检测分子内氢键。提出了单环和双环系统之间的生源关系。
