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Processing of a Sesquiterpene Lactone by Papilio glaucus Caterpillars

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Abstract

Papilio glaucus caterpillars encounter a diverse array of sesquiterpene lactones, including parthenolide, in the leaves of host plants Liriodendron tulipifera and Magnolia virginiana. These compounds are toxic to unadapted herbivores, and the development of P. glaucus caterpillars likely depends on their ability to excrete or detoxify them efficiently. A new metabolite of parthenolide, 2-α-hydroxydihydroparthenolide, identified by crystal structure determination and nuclear magnetic resonance, was present in the waste of the caterpillars. The parent compound was modified by the reduction of an α-methylene group, rendering the compound less reactive, and the addition of a hydroxyl group, which increases the polarity and prepares it for the conjugation reactions of phase II metabolism. Unmetabolized parthenolide was also present in large amounts in waste. P. glaucus larvae are apparently capable of excreting intact sesquiterpene lactones and sesquiterpene lactone metabolites during consumption of foliage rich in these compounds.

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Acknowledgments

The authors are grateful to Drs. Mark Scriber and James Maudsley for the collection of the female butterflies in June of 2001 and 2002. Dr. Nikolaus Fischer first observed the presence of sesquiterpene lactone peaks in the NMR spectra of the frass of the Magnolia-fed caterpillars and provided helpful advice and comments throughout the isolation.

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Correspondence to Cheryl Frankfater.

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Frankfater, C., Schühly, W., Fronczek, F.R. et al. Processing of a Sesquiterpene Lactone by Papilio glaucus Caterpillars. J Chem Ecol 31, 2541–2550 (2005). https://doi.org/10.1007/s10886-005-7612-z

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  • DOI: https://doi.org/10.1007/s10886-005-7612-z

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