Venom chemistry of the ant Myrmicaria melanogaster from Brunei.
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.
Jones
Tappey H
TH
Department of Chemistry, Virginia Military Institute, Lexington, Virginia 24450, USA. jonesth@vmi.edu
Voegtle
Heather L
HL
Miras
Heather M
HM
Weatherford
Robert G
RG
Spande
Thomas F
TF
Garraffo
H Martin
HM
Daly
John W
JW
Davidson
Diane W
DW
Snelling
Roy R
RR
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
D000470:Alkaloids; D000664:Amphibian Venoms; D000862:Ant Venoms; D007212:Indolizines