Biosynthetic pathway for production of a conjugated dienyl sex pheromone of a Plusiinae moth, Thysanoplusia intermixta.
Virgin females of Thysanoplusia intermixta (Lepidoptera; Noctuidae; Plusiinae) produce (5E,7Z)-5,7-dodecadienyl acetate as a main sex pheromone component. GC-MS analysis of the pheromone glands, which were treated with deuterated hexadecanoic, (Z)-11-hexadecenoic, and (Z)-7-dodecenoic acids, showed incorporation of the label into the dienyl component. Their incorporation rates confirmed that its biosynthesis proceeds in the following order: Delta11-desaturation of a C(16) acyl intermediate, chain shortening to a C(12) compound by beta-oxidation, Delta5-desaturation to produce a 5,7-dienyl system, reduction of the acyl group, and acetylation. These deuterated precursors also converted into a minor pheromone component, (Z)-7-docecenyl acetate, which might be prepared by the same pathway except for the step of Delta5-desaturation. While deuterium incorporation into the dienyl acetate was not observed in the extracts treated with other labeled dodecenoic acids with (E)-5-, (Z)-6-, and (E)-7-double bonds, the corresponding dodecenyl acetates were produced. This result showed low substrate specificity of the enzymes for reduction and acetylation. Labeled (Z)-10-hexadecenoic acid was not converted into a dodecenyl acetate, indicating the high substrate specificity of the enzyme for beta-oxidation.
Ono
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A
Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Technology, Koganei, 184-8588, Japan.
Imai
T
T
Inomata
S
S
Watanabe
A
A
Ando
T
T
D000085:Acetates / Q000378:metabolism*; D000818:Animals; D007851:Dodecanol / Q000031:analogs & derivatives; D005227:Fatty Acids / Q000096:biosynthesis* / Q000378:metabolism; D050356:Lipid Metabolism; D015394:Molecular Structure; D009036:Moths / Q000378:metabolism*; D010169:Palmitic Acids / Q000378:metabolism; D012724:Sex Attractants / Q000096:biosynthesis* / Q000737:chemistry
C460160:5,7-dodecadienyl acetate; D000085:Acetates; D005227:Fatty Acids; D010169:Palmitic Acids; D012724:Sex Attractants; D007851:Dodecanol; C093821:hexadecenoic acid