title: Venom chemistry of the ant Myrmicaria melanogaster from Brunei.
abstract: 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.
authors.affiliation: Department of Chemistry, Virginia Military Institute, Lexington, Virginia 24450, USA. jonesth@vmi.edu
authors.forename: Tappey H
authors.initials: TH
authors.lastname: Jones
authors.forename: Heather L
authors.initials: HL
authors.lastname: Voegtle
authors.forename: Heather M
authors.initials: HM
authors.lastname: Miras
authors.forename: Robert G
authors.initials: RG
authors.lastname: Weatherford
authors.forename: Thomas F
authors.initials: TF
authors.lastname: Spande
authors.forename: H Martin
authors.initials: HM
authors.lastname: Garraffo
authors.forename: John W
authors.initials: JW
authors.lastname: Daly
authors.forename: Diane W
authors.initials: DW
authors.lastname: Davidson
authors.forename: Roy R
authors.initials: RR
authors.lastname: Snelling
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification*; D000664:Amphibian Venoms / Q000737:chemistry; D000818:Animals; D000862:Ant Venoms / Q000737:chemistry*; D001000:Ants / Q000737:chemistry*; D002010:Brunei; D007212:Indolizines / Q000737:chemistry* / Q000302:isolation & purification*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000470:Alkaloids; D000664:Amphibian Venoms; D000862:Ant Venoms; D007212:Indolizines