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Aliphatic Esters as Targets of Esterase Activity in the Parsnip Webworm (Depressaria pastinacella)

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Abstract

As a specialist on the reproductive structures of Pastinaca sativa and species in the related genus Heracleum, the parsnip webworm (Depressaria pastinacella) routinely encounters a distinctive suite of phytochemicals in hostplant tissues. Little is known, however, about the detoxification mechanisms upon which this species relies to metabolize these compounds. In this study, larval guts containing hostplant tissues were homogenized, and metabolism was determined by incubating reactions with and without NADPH and analyzing for substrate disappearance and product appearance by gas chromatography–mass spectrometry. Using this approach, we found indications of carboxylesterase activity, in the form of appropriate alcohol metabolites for three aliphatic esters in hostplant tissues—octyl acetate, octyl butyrate, and hexyl butyrate. Involvement of webworm esterases in hostplant detoxification subsequently was confirmed with metabolism assays with pure compounds. This study is the first to implicate esterases in lepidopteran larval midgut metabolism of aliphatic esters, ubiquitous constituents of flowers and fruits. In addition, this method confirmed that webworms detoxify furanocoumarins and myristicin in their hostplants via cytochrome P450-mediated metabolism, and demonstrated that these enzymes also metabolize the coumarin osthol and the fatty acid derivative palmitolactone.

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Acknowledgments

This research was supported by a grant from the National Science Foundation (DEB 0816616).

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Authors and Affiliations

  1. Department of Entomology, University of Illinois at Urbana-Champaign, 320 Morrill Hall 505 S. Goodwin, Urbana, IL, 61801-3795, USA

    Arthur R. Zangerl, Ling-Hsiu Liao, Tania Jogesh & May R. Berenbaum

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  1. Arthur R. Zangerl
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  2. Ling-Hsiu Liao
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  3. Tania Jogesh
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  4. May R. Berenbaum
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Correspondence to May R. Berenbaum.

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Although this project was the brainchild of Arthur Zangerl, his untimely death prevented him from seeing this work in print. His quarter-century-long dedication to studying the interaction between parsnip webworms and wild parsnips was essential to making this system a model for chemical ecology studies.

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Zangerl, A.R., Liao, LH., Jogesh, T. et al. Aliphatic Esters as Targets of Esterase Activity in the Parsnip Webworm (Depressaria pastinacella). J Chem Ecol 38, 188–194 (2012). https://doi.org/10.1007/s10886-012-0073-2

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  • DOI: https://doi.org/10.1007/s10886-012-0073-2

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