| Title: | Characterization of geometrid sex pheromones by electrospray ionization time-of-flight mass spectrometry |
| Author(s): | Yamazawa H; Yamamoto M; Karasawa KI; Pu GQ; Ando T; |
| Address: | "Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan" |
| ISSN/ISBN: | 1076-5174 (Print) 1076-5174 (Linking) |
| Abstract: | "The utility of liquid chromatography combined with time-of-flight mass spectrometry (LC/TOFMS) was demonstrated for studies on chiral unsaturated epoxy compounds, sex pheromones produced mainly by female moths in the family Geometridae. By electrospray ionization (ESI), each synthetic epoxyalkadiene derived from (Z,Z,Z)-3,6,9-triene with a C(18)-C(23) straight chain showed three ion series, [M + NH(4)](+), [M + H](+) and [M - OH](+), with high resolution and good sensitivity, indicating its molecular formula. In addition to these, characteristic fragment ions at m/z M - 57 and M - 71 for the 3,4-epoxides and at m/z M - 123 and 123 for the 9,10-epoxides were detected, whereas the 6,7-epoxides did not produce fragment ions that reflected their structures. Monitoring these diagnostic ions during the LC/MS analysis of a gland extract, the natural sex pheromone of the mulberry looper was confirmed to be (Z,Z)-cis-9,10-epoxy-3,6-octadecadiene, which was separable from the other positional isomers on an ODS column. Furthermore, (Z,Z)-cis-3,4-epoxy-6,9-nonadecadiene secreted by the Japanese giant looper was analyzed with a chiral column, and the stereochemistry was determined directly" |
| Keywords: | "Animals Chromatography, Liquid Epoxy Compounds/chemical synthesis/chemistry Lepidoptera/*chemistry Sex Attractants/chemical synthesis/*chemistry *Spectrometry, Mass, Electrospray Ionization;" |
| Notes: | "MedlineYamazawa, Hiroyuki Yamamoto, Masanobu Karasawa, Kaoru Iida Pu, Guan-Qin Ando, Tetsu eng England 2003/03/20 J Mass Spectrom. 2003 Mar; 38(3):328-32. doi: 10.1002/jms.445" |
