| Title: | "Instrumental analysis of terminal-conjugated dienes for reexamination of the sex pheromone secreted by a nettle moth, Parasa lepida lepida" |
| Author(s): | Islam MD; Yamakawa R; Do ND; Numakura N; Suzuki T; Ando T; |
| Address: | "Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Technology, Tokyo, Japan" |
| Journal Title: | Biosci Biotechnol Biochem |
| ISSN/ISBN: | 1347-6947 (Electronic) 0916-8451 (Linking) |
| Abstract: | "Conjugated dienyl compounds make one of the main groups of lepidopteran sex pheromones, and GC has been frequently used to determine the configurations of the double bonds. However, the separation of two geometric isomers of a terminal-conjugated diene, such as 7,9-decadien-1-ol secreted by a nettle moth Parasa lepida lepida (Limacodidae), is assumed to be difficult. In order to clarify the chromatographic separation of the terminal dienes, 7,9-decadienyl and 9,11-dodecadienyl compounds (alcohols, acetates, and aldehydes) were analyzed by GC and HPLC. On a capillary GC column, the (E)-isomers flowed out slightly faster than the corresponding (Z)-isomers, but their peaks almost overlapped. On the other hand, HPLC equipped with an ODS column completely separated the two geometric isomers examined and the (Z)-isomers eluted from the column faster than the (E)-isomers without dependence on a functional group. In addition to undergoing direct HPLC analysis without derivatization, the dienyl alcohols were converted into 3,5-dinitrobenzoates and analyzed by LC-ESI-MS operated under the same reversed-phase condition. The two separated geometric isomers were sensitively monitored by negative ions at m/z 211, M, M+1, M+17, and M+31, which were characteristically derived from the benzoates. Based on these results, a pheromone extract of P. l. lepida was examined, and it was confirmed that the female moths exclusively produced the (Z)-isomer of the 7,9-diene. Furthermore, a GC-EAD analysis and a field evaluation with both geometrical isomers indicated that the mating communication of P. l. lepida is predominantly mediated with the (Z)-isomer" |
| Keywords: | "Alkenes/*analysis/chemistry/isolation & purification Animals Benzoates/analysis/chemistry Chromatography, Gas Chromatography, High Pressure Liquid Female Male Moths/*metabolism Sex Attractants/*chemistry/*metabolism Spectrometry, Mass, Electrospray Ioniza;" |
| Notes: | "MedlineIslam, M D Azharul Yamakawa, Rei Do, Nguyen Duc Numakura, Naoko Suzuki, Toshiro Ando, Tetsu eng England 2009/05/08 Biosci Biotechnol Biochem. 2009 May; 73(5):1156-62. doi: 10.1271/bbb.90047. Epub 2009 May 7" |
