Vittatalactone, a beta-lactone from the striped cucumber beetle, Acalymma vittatum.
A novel beta-lactone, vittatalactone (1), was isolated from collections of airborne volatile compounds from feeding male striped cucumber beetles, Acalymma vittatum. The structure of 1 was determined to be (3R,4R)-3-methyl-4-(1,3,5,7-tetramethyloctyl)oxetan-2-one by microderivatization, GC-MS, and NMR studies. The absolute configurations at C-2 and C-3 on the beta-lactone ring were assigned by use of the modified Mosher method, applied to the beta-hydroxy acid methyl ester resulting from methanolysis of 1. Biological activity of 1, possibly as an aggregation pheromone for A. vittatum, was indicated by electrophysiological studies using beetle antennae and by the production of 1 by feeding male, and not female, beetles.
Morris
Bruce D
BD
Department of Entomology, North Dakota State University, Fargo, North Dakota 58105, USA. bruce.morris@ndsu.nodak.edu
Smyth
Rebecca R
RR
Foster
Stephen P
SP
Hoffmann
Michael P
MP
Roelofs
Wendell L
WL
Franke
Stephan
S
Francke
Wittko
W
D000818:Animals; D001517:Coleoptera; D005260:Female; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008297:Male; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012724:Sex Attractants / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism
D007783:Lactones; D012724:Sex Attractants; C497413:vittatalactone