New C26 delta-lactones from the Dufour's gland of the urticating ant Tetramorium aculeatum.
(6R*)-[(2S*)-2-hydroxyheneicos-12-enyl]-5,6-dihydro-2H-pyran-2-one (1) degree is the major constituent of the secretion of freshly dissected Dufour's gland of the urticating ant Tetramorium aculeatum. In solution, compound 1 is slowly transformed into (1S*,5R*,7S*)-7-(nonadec-10-enyl)-2,6-dioxabicyclo[3.3.1] nonan-3-one (2) degrees on standing. The structures of compounds 1 and 2 have been established on the basis of their spectral and chemical properties. Compound 1 could be responsible for the urticating properties of the ant.
Merlin
P
P
Laboratory of Bio-Organic Chemistry, Faculty of Sciences, University of Brussels, Belgium.
Braekman
J C
JC
Daloze
D
D
Pasteels
J M
JM
Dejean
A
A
D000818:Animals; D001000:Ants / Q000737:chemistry*; D005088:Exocrine Glands / Q000737:chemistry / Q000378:metabolism; D007783:Lactones / Q000302:isolation & purification* / Q000633:toxicity; D009784:Occupational Diseases / Q000139:chemically induced; D014581:Urticaria / Q000139:chemically induced*
D007783:Lactones