Identification and biosynthesis of (E,E)-10,12-tetradecadienyl acetate in Spodoptera littoralis female sex pheromone gland.
A minor component of the sex pheromone gland of the Egyptian cotton leafworm, Spodoptera littoralis, has been identified as (E,E)-10,12-tetradecadienyl acetate. Structural elucidation has been carried out by isobutane-chemical ionization mass spectrometry of the fatty acyl biosynthetic precursor-derived methyl ester. To assign the stereochemistry of the double bonds, the four isomers of both 10,12-tetradecadienyl acetates and methyl 10,12-tetradecadienoates have been synthesized and their gas chromatography retention times and mass spectra have been compared to those of the corresponding natural compounds. Mass-labeling experiments showed that the (E,E)-10,12-tetradecadienoyl moiety is biosynthetically derived from (Z)-11-tetradecenoic acid in the insect pheromone gland.
Navarro
I
I
Departament de Química Organica Biològica, CID-CSIC, Barcelona, Spain.
Mas
E
E
Fabriàs
G
G
Camps
F
F
D000085:Acetates / Q000032:analysis* / Q000378:metabolism*; D000818:Animals; D005233:Fatty Alcohols / Q000032:analysis* / Q000378:metabolism*; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D010675:Pheromones / Q000032:analysis* / Q000138:chemical synthesis*; D018411:Spodoptera / Q000737:chemistry* / Q000378:metabolism*
C108651:10,12-tetradecadienyl acetate; D000085:Acetates; D005233:Fatty Alcohols; D010675:Pheromones