| Title: | "Vittatalactone, a beta-lactone from the striped cucumber beetle, Acalymma vittatum" |
| Author(s): | Morris BD; Smyth RR; Foster SP; Hoffmann MP; Roelofs WL; Franke S; Francke W; |
| Address: | "Department of Entomology, North Dakota State University, Fargo, North Dakota 58105, USA. bruce.morris@ndsu.nodak.edu" |
| ISSN/ISBN: | 0163-3864 (Print) 0163-3864 (Linking) |
| Abstract: | "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" |
| Keywords: | "Animals *Coleoptera Female Lactones/chemistry/*isolation & purification/pharmacology Male Molecular Structure Nuclear Magnetic Resonance, Biomolecular Sex Attractants/chemistry/*isolation & purification/pharmacology Stereoisomerism;" |
| Notes: | "MedlineMorris, Bruce D Smyth, Rebecca R Foster, Stephen P Hoffmann, Michael P Roelofs, Wendell L Franke, Stephan Francke, Wittko eng 2005/02/01 J Nat Prod. 2005 Jan; 68(1):26-30. doi: 10.1021/np049751v" |
