AUTHOR=Watanabe Hayaki , Matsui Aya , Inomata Sin-ichi , Yamamoto Masanobu , Ando Tetsu 

TITLE=Biosynthetic Pathway for Sex Pheromone Components Produced in a Plusiinae Moth, Plusia festucae

JOURNAL=Frontiers in Endocrinology

VOLUME=2

YEAR=2011

URL=https://www.frontiersin.org/journals/endocrinology/articles/10.3389/fendo.2011.00074

DOI=10.3389/fendo.2011.00074

ISSN=1664-2392

ABSTRACT=<p>While many Plusiinae species commonly secrete (<italic>Z</italic>)-7-dodecenyl acetate (Z7-12:OAc) as a key pheromone component, female moths of the rice looper (<italic>Plusia festucae</italic>) exceptionally utilize (<italic>Z</italic>)-5-dodecenyl acetate (Z5-12:OAc) to communicate with their partners. GC–MS analysis of methyl esters derived from fatty acids included in the pheromone gland of <italic>P. festucae</italic> showed a series of esters monounsaturated at the ω7-position, i.e., (<italic>Z</italic>)-5-dodecenoate, (<italic>Z</italic>)-7-tetradecenoate, (<italic>Z</italic>)-9-hexadecenoate (Z9-16:Me), and (<italic>Z</italic>)-11-octadecenoate (Z11-18:Me). By topical application of D<sub>3</sub>-labled palmitic acid (16:Acid) and stearic acid (18:Acid) to the pheromone glands, similar amounts of D<sub>3</sub>-Z5-12:OAc were detected. The glands treated with D<sub>13</sub>-labeled monoenoic acids (Z9-16:Acid and Z11-18:Acid), which were custom-made by utilizing an acetylene coupling reaction with D<sub>13</sub>-1-bromohexane, also produced similar amounts of D<sub>13</sub>-Z5-12:OAc. These results suggested that Z5-12:OAc was biosynthesized by ω7-desaturase with low substrate specificity, which could introduce a double bond at the 9-position of a 16:Acid derivative and the 11-position of an 18:Acid derivative. Additional experiments with the glands pretreated with an inhibitor of chain elongation supported this speculation. Furthermore, a comparative study with another Plusiinae species (<italic>Chrysodeixis eriosoma</italic>) secreting Z7-12:OAc indicated that the β-oxidation systems of <italic>P. festucae</italic> and <italic>C. eriosoma</italic> were different.</p>