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Biosynthesis of sex pheromone components from linolenic acid in arctiid moths
Author(s) -
Rule Geoffrey S.,
Roelofs Wendell L.
Publication year - 1989
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/arch.940120203
Subject(s) - biology , linolenic acid , pheromone , decarboxylation , aldehyde , fatty acid , malonic acid , biochemistry , sex pheromone , biosynthesis , stereochemistry , botany , enzyme , chemistry , linoleic acid , catalysis
Sex pheromone components of two species of arctiid moths, Estigmene acrea and Phragmatobia fuliginosa , were shown to be derived from linolenic acid. Female pupae were injected with radiolabeled malonic acid or an 18‐, 20‐, 21‐, or 22‐carbon triunsaturated fatty acid, and the pheromone components from emerged adults analyzed for radioactivity. The data support a biosynthetic pathway in which the 21‐carbon pheromone component,(Z, Z)‐3,6‐cis‐9,10‐epoxyheneicosadiene, of these moths is produced by chain elongation of linolenic acid to docosatrienoic acid with subsequent reductive decarboxylation. The 18‐carbon aldehyde components,(Z, Z)‐9,12‐octadecadienal and (Z, Z, Z)‐9,12,15‐octadecatrienal, of E. acrea are produced from linoeic and linolenic acids directly. No detectable amounts of intermediate 20‐, 21‐, or 22‐carbon fatty acid precursors were found in the gland of E. acrea .