| Title: | "Synthesis and characterization of hexadecadienyl compounds with a conjugated diene system, sex pheromone of the persimmon fruit moth and related compounds" |
| Author(s): | Nishida T; Vang VL; Yamazawa H; Yoshida R; Naka H; Tsuchida K; Ando T; |
| Address: | "Graduate School of Bio-Applications and Systems Engineering (BASE), Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan" |
| Journal Title: | Biosci Biotechnol Biochem |
| ISSN/ISBN: | 0916-8451 (Print) 0916-8451 (Linking) |
| Abstract: | "Hexadecadien-1-ol and the derivatives (acetate and aldehyde) with a conjugated diene system have recently been identified from a pheromone gland extract of the persimmon fruit moth (Stathmopoda masinissa), a pest insect of persimmon fruits distributed in East Asia. The alcohol and acetate showed their base peaks at m/z 79 in a GC-MS analysis by electron impact ionization, but the aldehyde produced a unique base peak at m/z 84, suggesting a 4,6-diene structure. To confirm this inference, four geometrical isomers of each 4,6-hexadecadienyl compound were synthesized by two different routes in which one of two double bonds was furnished in a highly stereoselective manner. Separation of the two isomers synthesized together by each route was facilely accomplished by preparative HPLC. Their mass spectra coincided well with those of natural components, indicating that they were available for use as authentic standards for determining the configuration of the natural pheromone. Furthermore, other hexadecadienyl compounds, including the conjugated diene system between the 3- and 10-positions, were synthesized to accumulate the spectral data of pheromone candidates. 5,7-Hexadecadienal interestingly showed the base peak at m/z 80; meanwhile, the base peaks of its alcohol and acetate were detected at m/z 79 like the corresponding 4,6-dienes. The base peaks of all 6,8-, 7,9-, and 8,10-dienes universally appeared at m/z 67 like 9,11-, 10,12-, and 13,15-dienes, the spectra of which have already been published. Although 3,5-hexadecadienal was not prepared, base peaks at m/z 67 and 79 were recorded for the alcohol and acetate, respectively" |
| Keywords: | "Acetates Alcohols Aldehydes Alkadienes/*chemical synthesis/pharmacology Alkanes Animals Diospyros Hydrocarbons, Aromatic/chemical synthesis/pharmacology Magnetic Resonance Spectroscopy Male Mass Spectrometry *Moths Sex Attractants/*chemistry Stereoisomeri;" |
| Notes: | "MedlineNishida, Takanobu Vang, Van Le Yamazawa, Hiroyuki Yoshida, Ryuji Naka, Hideshi Tsuchida, Koji Ando, Tetsu eng England 2003/06/06 Biosci Biotechnol Biochem. 2003 Apr; 67(4):822-9. doi: 10.1271/bbb.67.822" |
