title: Pheromone biosynthetic pathways in the moths Heliothis subflexa and Heliothis virescens.
abstract: Sex pheromones of many moth species have relatively simple structures consisting of a hydrocarbon chain with a functional group and one to several double bonds. These sex pheromones are derived from fatty acids through specific biosynthetic pathways. We investigated the incorporation of deuterium-labeled tetradecanoic, hexadecanoic, and octadecanoic acid precursors into pheromone components of Heliothis subflexa and Heliothis virescens. The two species utilize (Z)11-hexadecenal as the major pheromone component, which is produced by Delta11 desaturation of hexadecanoic acid. H. subflexa also produced (Z)11-hexadecanol and (Z)-11-hexadecenyl acetate via Delta11 desaturation. In H. subflexa, octadecanoic acid was used to biosynthesize the minor pheromone components (Z)9-hexadecenal, (Z)9-hexadecenol, and (Z)9-hexadecenyl acetate. These minor components are produced by Delta11 desaturation of octadecanoic acid followed by one round of chain-shortening. In contrast, H. virescens used hexadecanoic acid as a substrate to form (Z)11-hexadecenal and (Z)11-hexadecenol and hexadecenal. H. virescens also produced (Z)9-tetradecenal by Delta11 desaturation of the hexadecanoic acid followed by one round of chain-shortening and reduction. Tetradecanoic acid was not utilized as a precursor to form Z9-14:Ald in H. virescens. This labeling pattern indicates that the Delta11 desaturase is the only active desaturase present in the pheromone gland cells of both species.
authors.affiliation: Department of Entomology, Iowa State University, Ames, Iowa 50011-3222, USA.
authors.forename: Man-Yeon
authors.initials: MY
authors.lastname: Choi
authors.forename: Astrid
authors.initials: A
authors.lastname: Groot
authors.forename: Russell A
authors.initials: RA
authors.lastname: Jurenka
mesh_terms: D000818:Animals; D003903:Deuterium; D044943:Fatty Acid Desaturases / Q000378:metabolism; D008401:Gas Chromatography-Mass Spectrometry; D008954:Models, Biological; D009036:Moths / Q000378:metabolism*; D010169:Palmitic Acids / Q000378:metabolism; D011799:Quinazolines / Q000378:metabolism; D012724:Sex Attractants / Q000096:biosynthesis*
chemical_list: D010169:Palmitic Acids; D011799:Quinazolines; D012724:Sex Attractants; C059207:tetrodonic acid; C093821:hexadecenoic acid; D003903:Deuterium; D044943:Fatty Acid Desaturases