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« Previous AbstractField tests of syntheticManduca sexta sex pheromone    Next AbstractBiosynthesis of fatty acid amide elicitors of plant volatiles by insect herbivores »

Bioorg Med Chem


Title:The integral role of triacyl glycerols in the biosynthesis of the aldehydic sex pheromones of Manduca sexta (L)
Author(s):Tumlinson JH; Teal PE; Fang N;
Address:"Insect Attractants, Behavior, and Basic Biology Research Laboratory, U.S. Department of Agriculture, Gainesville, FL 32604, USA"
Journal Title:Bioorg Med Chem
Year:1996
Volume:4
Issue:3
Page Number:451 - 460
DOI: 10.1016/0968-0896(96)00025-9
ISSN/ISBN:0968-0896 (Print) 0968-0896 (Linking)
Abstract:"In a gland located near the tip of their abdomens, Manduca sexta females produce a pheromone blend comprised of hexadecanal, (Z)-9-hexadecenal, (Z)- and (E)-11-hexadecenal, (E,Z)- and (E,E)-10,12-hexadecadienal, and (E,E,Z)- and (E,E,E)-10,12,14-hexadecatrienal. These aldehydes are produced and released by evaporation from the surface of the gland only during a discrete period of the night. They are not stored in the gland and are found there only in very small amounts, if at all, during other times of the photoperiod. However, fatty acyl analogues of the pheromone aldehydes are present in the gland in relatively large amounts, primarily as components of triacyl glycerols, continuously from eclosion of the adults until death. The unsaturated components are produced from hexadecanoate, which is desaturated to the monoenes. Then, (Z)-11-hexadecenoate is desaturated and isomerized to form the conjugated dienes and ultimately the conjugated trienes. The fatty acyl precursors of the pheromones, stored as components of triacyl glycerols, are converted into aldehydes by a process triggered by a pheromone biosynthesis activating neuropeptide (PBAN), produced in the brain-subesophageal complex. It is not yet clear whether this conversion involves direct reduction of the acyl groups to aldehydes or reduction to alcohols followed by oxidation to aldehydes"
Keywords:"Aldehydes/*metabolism Alkenes/metabolism Animals Chromatography, High Pressure Liquid Fatty Acids/metabolism Female Manduca/drug effects/*metabolism Neuropeptides/pharmacology Sex Attractants/*biosynthesis Triglycerides/*metabolism;"
Notes:"MedlineTumlinson, J H Teal, P E Fang, N eng England 1996/03/01 Bioorg Med Chem. 1996 Mar; 4(3):451-60. doi: 10.1016/0968-0896(96)00025-9"

 
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