Caste-specific tyramides from Myrmicine ants.
Analysis of the extracts of male ants of Monomorium minimum and Monomorium ebeninum by GC-MS and GC-FTIR revealed the presence of tyramides 2 and 4c, for which the structures were established by comparison with synthetic samples. These compounds and their analogues 1 and 3 were also found in males of other Monomorium species, males of Myrmicaria opaciventris, and males of several Solenopsis (Diplorhoptrum) species. Vapor-phase FTIR spectra revealed critically important structural clues to two of the tyramides, which had methyl branching in the tyramide acyl moiety. Tyramide 4c exhibited a strong intramolecular amide NH hydrogen bond where an alpha-keto group was deduced to be present in the acyl moiety and also showed the overlap of this ketone group frequency with that of the amide nu(C horizontal lineO). The biological function of these compounds is uncertain; however, their role in ant-mating behavior may be suggested by a large body of evidence.
Jones
Tappey H
TH
Department of Chemistry, Virginia Military Institute, Lexington, Virginia 24450, USA. jonesth@vmi.edu
Garraffo
H Martin
HM
Spande
Thomas F
TF
Andriamaharavo
Nirina R
NR
Gorman
Jeffrey S T
JS
Snyder
Alexander J
AJ
Jeter
Andrew W
AW
Torres
Juan A
JA
Snelling
Roy R
RR
Daly
John W
JW
D000818:Animals; D001000:Ants / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D008297:Male; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014439:Tyramine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014768:Virginia
D014439:Tyramine