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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.
