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Acylated quinic acids are the main salicortin metabolites in the lepidopteran specialist herbivore Cerura vinula

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Feistel,  Felix
Research Group Biosynthesis / NMR, MPI for Chemical Ecology, Max Planck Society;

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Paetz,  Christian
Research Group Biosynthesis / NMR, MPI for Chemical Ecology, Max Planck Society;

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Menezes,  Riya Christina
Research Group Mass Spectrometry, MPI for Chemical Ecology, Max Planck Society;

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Veit,  Daniel
MPI for Chemical Ecology, Max Planck Society;

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Schneider,  Bernd
Research Group Biosynthesis / NMR, MPI for Chemical Ecology, Max Planck Society;

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Citation

Feistel, F., Paetz, C., Menezes, R. C., Veit, D., & Schneider, B. (2018). Acylated quinic acids are the main salicortin metabolites in the lepidopteran specialist herbivore Cerura vinula. Journal of Chemical Ecology. doi:10.1007/s10886-018-0945-1.


Cite as: https://hdl.handle.net/21.11116/0000-0000-DFA7-9
Abstract
Salicortin is a phenolic glucoside produced in Salicaceae as a chemical defense against herbivory. The specialist lepidopteran herbivorous larvae of Cerura vinula are able to overcome this defense. We examined the main frass constituents of C. vinula fed on Populus nigra leaves, and identified 11 quinic acid derivatives with benzoate and/or salicylate substitution.We asked whether the compounds are a result of salicortin breakdown and sought answers by carrying out feeding experiments with highly 13C-enriched salicortin. Using HRMS and NMR analyses, we were able to confirm that salicortin metabolism in C. vinula proceeds through deglucosylation and ester hydrolysis, after which saligenin is oxidatively transformed into salicylic acid and, eventually, conjugated to quinic acid. To the best of our knowledge, this is the first report of a detoxification pathway based on conjugation with quinic acid.