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Biosci Biotechnol Biochem

Title:		"Synthesis and characterization of 3,13- and 2,13-octadecadienyl compounds for identification of the sex pheromone secreted by a clearwing moth, Nokona pernix"
Author(s):		Naka H; Nakazawa T; Sugie M; Yamamoto M; Horie Y; Wakasugi R; Arita Y; Sugie H; Tsuchida K; Ando T;
Address:		"Entomology Group, Department of Biological Safety, National Institute for Agro-Environmental Sciences (NIAES), Ibaraki, Japan"
Journal Title:		Biosci Biotechnol Biochem
Year:		2006
Volume:		70
Issue:		2
Page Number:		508 - 516
DOI:		10.1271/bbb.70.508
ISSN/ISBN:		0916-8451 (Print) 0916-8451 (Linking)
Abstract:		"Several geometrical isomers of 3,13- and 2,13-octadecadien-1-ols and their acetates were synthesized starting from 1,8-octanediol or 1,9-nonanediol utilizing acetylene coupling reactions. In addition to commercially available compounds, all geometrical isomers of each dienyl compound were analyzed by NMR and GC-MS to accumulate chemical data for studies of sex pheromones secreted from clearwing moths classified into the family Sesiidae of Lepidoptera. Although acetoxy derivatives of the 3,13- and 2,13-dienes showed almost the same mass spectra, the alcohols were distinguished by comparing the relative intensities of [M-18](+) at m/z 248, indicating direct differentiation of the two positional isomers without derivatization. Furthermore, each geometrical isomer eluted from a high-polar GC column with a different retention time. Base on these data, a pheromone gland extract of a sesiid moth, Nokona pernix, was analyzed by GC-EAD and GC-MS, and two EAG-active components were identified, viz., the (3E,13Z)- and (3Z,13Z)-isomers of 3,13-octadecadien-1-ol in a ratio of 9:1. In the field, the synthetic compounds mixed in 9:1 ratio attracted N. pernix males well, while a single component scarcely attracted the males. The number of attracted males peaked in the middle of June, and a small second peak was observed in August"
Keywords:		Animals Gas Chromatography-Mass Spectrometry Magnetic Resonance Spectroscopy Male Molecular Structure Moths/chemistry/*metabolism Sex Attractants/*chemical synthesis/chemistry/*metabolism;
Notes:		"MedlineNaka, Hideshi Nakazawa, Tomotake Sugie, Mieko Yamamoto, Masanobu Horie, Yoshiteru Wakasugi, Ryohei Arita, Yutaka Sugie, Hajime Tsuchida, Koji Ando, Tetsu eng Research Support, Non-U.S. Gov't England 2006/02/24 Biosci Biotechnol Biochem. 2006 Feb; 70(2):508-16. doi: 10.1271/bbb.70.508"