PMID: 11607415Jul 15, 1993Paper

Insect pheromone biosynthesis: stereochemical pathway of hydroxydanaidal production from alkaloidal precursors in Creatonotos transiens (Lepidoptera, Arctiidae)

Proceedings of the National Academy of Sciences of the United States of America
S SchulzJ Meinwald

Abstract

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 spectrometry. These analyses indicate that heliotrine is initially epimerized to (7S)-epiheliotrine by oxidation to the corresponding ketone followed by stereospecific reduction. The order of the subsequent steps is (i) aromatization of the dihydropyrrole ring, (ii) ester hydrolysis, and (iii) oxidation of the resulting primary alcohol to the final aldehyde. The ecological implications of this insect's ability (and the inability of another moth, Utetheisa ornatrix) to use representatives of two stereochemical families of alkaloids as pheromone precursors are discussed.

References

Jan 1, 1969·Journal of the Chemical Society. Perkin Transactions 1·A R Mattocks
May 15, 1993·Proceedings of the National Academy of Sciences of the United States of America·C W LaMunyon, T Eisner

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Citations

Jun 4, 2008·Journal of Chemical Ecology·Richard K Zimmer, Cheryl Ann Zimmer
Apr 23, 2003·Insect Biochemistry and Molecular Biology·T HartmannJ M Pasteels
Jul 16, 1999·Insect Biochemistry and Molecular Biology·J A TillmanG J Blomquist
Dec 1, 2001·Annual Review of Entomology·Ritsuo Nishida
Mar 21, 2016·European Journal of Medicinal Chemistry·Ahmed M Gouda, Ahmed H Abdelazeem
Dec 19, 2006·Insect Biochemistry and Molecular Biology·Till BeuerleThomas Hartmann
Sep 8, 2019·Journal of Chemical Ecology·Patrick StammStefan Schulz
Apr 5, 2018·Scientific Reports·Keiichi HondaYasuyuki Honda
Apr 27, 2018·Frontiers in Physiology·Michael Wink
Jan 5, 2021·Frontiers in Physiology·Yaling ZhangXinming Yin
May 10, 2007·The Journal of Experimental Biology·Ryan P Ferrer, Richard K Zimmer
May 10, 2007·The Journal of Experimental Biology·Ryan P Ferrer, Richard K Zimmer
Sep 22, 2021·Chembiochem : a European Journal of Chemical Biology·Stephanie EhlersStefan Schulz

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