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

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, 44(5), 497-509. doi:10.1007/s10886-018-0945-1.

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http://dx.doi.org/10.1007/s10886-018-0945-1 (Publisher version)
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 Creators:
Feistel, Felix1, 2, Author              
Paetz, Christian1, Author              
Menezes, Riya Christina3, Author              
Veit, Daniel4, Author              
Schneider, Bernd1, Author              
Affiliations:
1Research Group Biosynthesis / NMR, MPI for Chemical Ecology, Max Planck Society, ou_421898              
2IMPRS on Ecological Interactions, MPI for Chemical Ecology, Max Planck Society, Jena, DE, ou_421900              
3Research Group Mass Spectrometry, MPI for Chemical Ecology, Max Planck Society, ou_421899              
4MPI for Chemical Ecology, Max Planck Society, ou_24027              

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 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.

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 Dates: 2018-03-082018-03-172018-05
 Publication Status: Published in print
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 Identifiers: Other: NMR253
DOI: 10.1007/s10886-018-0945-1
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Title: Journal of Chemical Ecology
Source Genre: Journal
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Publ. Info: New York : Plenum Pub. Corp.
Pages: - Volume / Issue: 44 (5) Sequence Number: - Start / End Page: 497 - 509 Identifier: ISSN: 0098-0331
CoNE: https://pure.mpg.de/cone/journals/resource/954925466258