Venom Chemistry of the Ant Myrmicaria melanogaster from Brunei
| Autor: | Diane W. Davidson, Roy R. Snelling, John W. Daly, Heather M. Miras, H. Martin Garraffo, Thomas F. Spande, Tappey H. Jones, Heather L. Voegtle, Robert G. Weatherford |
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| Rok vydání: | 2007 |
| Předmět: |
Brunei
Stereochemistry Monoterpene Pharmaceutical Science Pyrrolidine Analytical Chemistry Structure-Activity Relationship chemistry.chemical_compound Alkaloids Drug Discovery Animals Pharmacology Limonene biology Ant Venoms Ants Chemistry Organic Chemistry Myrmicaria Indolizines Stereoisomerism biology.organism_classification Terpenoid ANT Aculeata Complementary and alternative medicine Myrcene Amphibian Venoms Molecular Medicine |
| Zdroj: | Journal of Natural Products. 70:160-168 |
| ISSN: | 1520-6025 0163-3864 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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