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Sequestration of Plant-Derived Phenolglucosides by Larvae of the Leaf Beetle Chrysomela lapponica: Thioglucosides as Mechanistic Probes

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Abstract

Feeding larvae of Chrysomela lapponica (Coleoptera: Chrysomelidae) acquire characteristic O-glucosides from the leaves of their food plants. The glucosides are selectively channeled from the gut to the defensive gland. Subsequent enzymatic transformations generate a blend of different defensive compounds, e.g., salicylaldehyde and two series of 2-methylbutyl and isobutyryl esters. By using systematically modified and hydrolysis-resistant thioglucosides as structural mimics of the plant-derived glucosides, e.g., salicin and its o-, m-, and p-isomers 1, 2, and 3; o-, m-, and p-cresols 5, 6, 7; along with thioglucosides of 2-phenylethanol 9 and (3Z)-hexenol 10, we demonstrated that the larvae of C. lapponica are able to sequester a broad range of structurally different thioglucosides with comparable efficiency. This sharply contrasts with the sequestration habitus previously observed in Chrysomela populi and Phratora vitellinae, which secrete almost pure salicylaldehyde and posses a highly specific transport mechanism for salicin (Kuhn et al., Proc. Natl. Acad. Sci. USA 101:13808–13813, 2004). Also, neither C. lapponica nor C. populi sequester in their gland the thioglucoside of 8-hydroxygeraniol, the mimic of the glucoside specifically transported by larvae secreting iridoid monoterpenes (Phaedon cochleariae, Gastrophysa viridula). Accordingly, leaf beetle larvae possess selective membrane carriers in their gut and their defensive systems that match the orientation of the functional groups of glucosides from their food plants probably by embedding the substrate in a network of hydrogen bonds inside the membrane carriers. The synthesis and the spectroscopic properties of the test compounds along with a comparative evaluation of the transport capabilities of larvae of C. populi and C. lapponica are described.

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Acknowledgments

We thank Angelika Berg for rearing of the insects, and Dr. A. Burse for proofreading of the manuscript. Financial support by the Fonds der Chemischen Industrie, Frankfurt a.M. and from the Belgian Fund for Join Basic Research is gratefully acknowledged.

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Authors and Affiliations

  1. Max Planck Institute for Chemical Ecology, Hans-Knöll-Str. 8, D-07745, Jena, Germany

    Jürgen Kuhn, Eva M. Pettersson, Birte K. Feld, Lihua Nie, Karla Tolzin-Banasch & Wilhelm Boland

  2. Ecologia y Conservation de Fauna Silvestre, El Colegio de la Frontera Sur, AP 424, Chetumal, Quinta Roo, Mexico

    Salima Machkour M’Rabet

  3. Behavioral and Evolutionary Biology, Université Libre de Bruxelles, P.O. Box 160/12, Avenue F.D. Roosevelt, 1050, Brussels, Belgium

    Jacques Pasteels

  4. Max Planck Institute for Chemical Ecology, Hans-Knöll-Str. 8, D-07745, Jena, Germany

    Wilhelm Boland

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  1. Jürgen Kuhn
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Correspondence to Wilhelm Boland.

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Kuhn, J., Pettersson, E.M., Feld, B.K. et al. Sequestration of Plant-Derived Phenolglucosides by Larvae of the Leaf Beetle Chrysomela lapponica: Thioglucosides as Mechanistic Probes. J Chem Ecol 33, 5–24 (2007). https://doi.org/10.1007/s10886-006-9201-1

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