Biosynthesis of the Spiroacetal Suite in Bactrocera tryoni

Authors

  • Dr. Yvonne K. Booth,

    1. School of Chemistry and Molecular Biosciences, The University of Queensland, St. Lucia, Brisbane, 4072 (Australia), Fax: (+61) 7-3365-4299
    Search for more papers by this author
  • Prof. William Kitching,

    1. School of Chemistry and Molecular Biosciences, The University of Queensland, St. Lucia, Brisbane, 4072 (Australia), Fax: (+61) 7-3365-4299
    Search for more papers by this author
  • Prof. James J. De Voss

    Corresponding author
    1. School of Chemistry and Molecular Biosciences, The University of Queensland, St. Lucia, Brisbane, 4072 (Australia), Fax: (+61) 7-3365-4299
    • School of Chemistry and Molecular Biosciences, The University of Queensland, St. Lucia, Brisbane, 4072 (Australia), Fax: (+61) 7-3365-4299
    Search for more papers by this author

Abstract

In pursuit of a more environmentally benign method of controlling the highly pestiferous Queensland fruit fly, Bactrocera tryoni, the biosynthesis of the minor components in the suite of spiroacetals released by females has been investigated. This follows on the biosynthetic definition of the pathway to the major component, (E,E)-1. The origins of the C12 and C13 spiroacetals (E,E)-2 and (E,E)-3, respectively, have been investigated by the administration of over 30 deuterated potential precursors. Analysis of the relative incorporation levels and identification of some of the exceptionally minor spiroacetals that were biosynthesised established that B. tryoni processes fatty acids to 2,6-dioxygenated precursors by a modified β-oxidation pathway, with a suite of putative cytochromes P450 employed in the crucial oxidative steps, prior to cyclisation of the proposed ketodiol.

Ancillary