Venom Chemistry of the Ant Myrmicaria melanogaster from Brunei
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- 作者：Tappey H. Jones ; Heather L. Voegtle ; Heather M. Miras ; Robert G. Weatherford ; Thomas F. Spande ; H. Martin Garraffo ; John W. Daly ; Diane W. Davidson ; Roy R. Snelling
- 刊名：Journal of Natural Products
- 出版年：2007
- 出版时间：February 2007
- 年：2007
- 卷：70
- 期：2
- 页码：160 - 168
- 全文大小：179K
- 年卷期：v.70,no.2(February 2007)
- ISSN：1520-6025
文摘
Analysis of the extracts of the ant Myrmicaria melanogaster from Brunei in the Indonesian archipelago by GC-MS andGC-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 monoterpenehydrocarbons 
fchars/beta2.gif" BORDER=0 ALIGN="middle">-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 studyutilized vapor-phase infrared analysis for the assignment of stereochemistry using Bohlmann bands for the bicyclicalkaloids and, in the case of 10a, the detection of an intramolecular hydrogen bond. A biogenetic relationship betweenthe mono- and bicyclic ring systems is proposed.
fchars/beta2.gif" BORDER=0 ALIGN="middle">-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 studyutilized vapor-phase infrared analysis for the assignment of stereochemistry using Bohlmann bands for the bicyclicalkaloids and, in the case of 10a, the detection of an intramolecular hydrogen bond. A biogenetic relationship betweenthe mono- and bicyclic ring systems is proposed.