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Sex pheromone biosynthesis in the tortricid moth Planotortrix excessana (Walker) involves chain‐shortening of palmitoleate and oleate
Author(s) -
Foster Stephen P.
Publication year - 1998
Publication title -
archives of insect biochemistry and physiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.576
H-Index - 66
eISSN - 1520-6327
pISSN - 0739-4462
DOI - 10.1002/(sici)1520-6327(1998)37:2<158::aid-arch4>3.0.co;2-q
Subject(s) - biosynthesis , pheromone , fatty acid , stereochemistry , palmitic acid , oleic acid , chemistry , stearic acid , biochemistry , sex pheromone , biology , organic chemistry , gene , botany
Biosynthesis of the sex pheromone components, ( Z )‐5‐tetradecenyl acetate (Z5‐14:OAc) and ( Z )‐7‐tetradecenyl acetate (Z7‐14:OAc), was investigated in the New Zealand tortricid moth Planotortrix excessana (Walker) by fatty acid methyl ester (FAME) analysis of base‐methanolyzed extracts of lipids in the sex pheromone gland and through application of various labelled fatty acids. Analysis of the base‐methanolyzed gland extracts revealed common FAMEs, including methyl oleate and methyl palmitoleate, as well as the FAMEs of the putative precursors, methyl ( Z )‐5‐tetradecenoate and methyl ( Z )‐7‐tetradecenoate. Application of labelled, saturated fatty acids, myristic, palmitic, and stearic did not result in any significant incorporation of label into either of the unsaturated pheromone components, although label was incorporated into tetradecyl acetate (14:OAc). In contrast, application of labelled oleic acid resulted in incorporation of label into Z5‐14:OAc but not into Z7‐14:OAc or into 14:OAc, whereas application of labelled palmitoleic acid resulted in incorporation of label into Z7‐14:OAc but not into Z5‐14:OAc or 14:OAc. These data support a route for biosynthesis of Z5‐14:OAc and Z7‐14:OAc in this species by limited β‐oxidation of the common fatty acyl moieties, respectively, oleate (involving two cycles of 2‐carbon chain‐shortening) and palmitoleate (involving only one cycle of 2‐carbon chain‐shortening), and apparently involving no desaturase (other than the common Δ9) specific to sex pheromone biosynthesis. Interestingly, P. excessana females biosynthesize the same component (Z5‐14:OAc) from an entirely different route from that of the related species Ctenopseustis obliquana (which biosynthesizes Z5‐14:OAc by Δ5‐desaturation of myristate). Additionally, the pheromone biosynthesis activating neuropeptide (PBAN) stimulates pheromone biosynthesis in this species. Arch. Insect Biochem. Physiol. 37:158–167, 1998. © 1998 Wiley‐Liss, Inc.