Journal of Chemical Ecology

, Volume 33, Issue 12, pp 2266–2280 | Cite as

Insect-synthesised Retronecine Ester Alkaloids: Precursors of the Common Arctiine (Lepidoptera) Pheromone Hydroxydanaidal

Article

Abstract

Many pyrrolizidine alkaloid (PA)-adapted insects convert PAs sequestered from their larval host plants into “insect-PAs” in which the acid components of the alkaloids are replaced by small, branched aliphatic 2-hydroxy acids of insect origin. It has been proposed that insect-PAs are precursors of the pheromone hydroxydanaidal in male Estigmene acrea moths, but it is not clear why they are specifically required or what the structural features or chemical properties are that make insect-PAs more suitable for conversion into hydroxydanaidal than superficially similar alkaloids of plant origin. Evidence is presented that insect-PAs are also precursors of hydroxydanaidal in the polyphageous arctiine, Creatonotos transiens, and a new biosynthetic pathway to hydroxydanaidal is proposed that has a mandatory requirement for insect-PAs as intermediates.

Keywords

Pyrrolizidine alkaloids Creatonotos transiens Arctiinae Insect-PAs Male pheromones Hydroxydanaidal Biosynthesis 

Notes

Acknowledgments

Thanks to Monika Siegel and Anita Kiesel for technical support and Steven M. Colegate for LC-ESI-MS confirming molecular weight data.

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Copyright information

© Springer Science+Business Media, LLC 2007

Authors and Affiliations

  1. 1.CSIRO Livestock IndustriesGeelongAustralia
  2. 2.Forstzoologisches InstitutAlbert-Ludwigs-UniversitätFreiburgGermany

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