Biosynthesis of Pyrrolidine Alkaloid-Derived Pheromones in the Arctiid Moth, Creatonotos transiens: Stereochemical Conversion of Heliotrine
نویسندگان
چکیده
M. Wink* Universität München, Pharmazeutische Biologie, Karlstraße 29, D-8000 München 2, Bundesrepublik Deutschland D. Schneider Max-Planck-Institut für Verhaltensphysiologie, D-8131 Seewiesen, Bundesrepublik Deutschland L. Wit te Technische Universität Braunschweig, Institut für Organische Chemie, Hagenring 30, D-3300 Braunschweig, Bundesrepublik Deutschland Z. Naturforsch. 43c, 737-741 (1988); received May 4/June 13, 1988 Creatonotos, Pyrrolizidine Alkaloids, Heliotrine, Male Pheromone, Hydroxydanaidal In larvae and later developmental stages of Creatonotos transiens, which had been reared on the pyrrolizidine alkaloid 75-heliotrine, a new major metabolite was detected by capillary GLC. The structure of this metabolite was determined by GLC-MS (EI, CI-MS) and C NMR to be 1Rheliotrine and 7/?-heliotrine-N-oxide. 7/?-Heliotrine is likely to be the direct precursor for the pheromone R( — )-hydroxydanaidal.
منابع مشابه
Insect pheromone biosynthesis: stereochemical pathway of hydroxydanaidal production from alkaloidal precursors in Creatonotos transiens (Lepidoptera, Arctiidae).
The mechanism by which the moth Creatonotos transiens produces its male pheromone, (7R)-hydroxydanaidal, from heliotrine, an alkaloidal precursor of opposite (7S) stereochemistry, was investigated. Specifically deuteriated samples of heliotrine and epiheliotrine were prepared and fed to C. transiens larvae, and the steps in the biosynthetic process were monitored by gas chromatography/mass spec...
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