Feistel Felix, Paetz Christian, Menezes Riya C, Veit Daniel, Schneider Bernd
Max Planck Institute for Chemical Ecology, Hans-Knöll-Straße 8, Beutenberg Campus, D-07745, Jena, Germany.
J Chem Ecol. 2018 May;44(5):497-509. doi: 10.1007/s10886-018-0945-1. Epub 2018 Mar 17.
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 C-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.
水杨苷是杨柳科植物产生的一种酚类糖苷，作为一种化学防御机制抵御食草动物。葡萄天蛾（Cerura vinula）的专食性鳞翅目食草幼虫能够克服这种防御机制。我们研究了以黑杨叶为食的葡萄天蛾的主要粪便成分，鉴定出11种具有苯甲酸酯和/或水杨酸酯取代基的奎尼酸衍生物。我们询问这些化合物是否是水杨苷分解的产物，并通过用高碳富集的水杨苷进行喂食实验来寻找答案。通过高分辨质谱（HRMS）和核磁共振（NMR）分析，我们能够证实葡萄天蛾体内水杨苷的代谢过程是通过去糖基化和酯水解进行的，之后水杨醇被氧化转化为水杨酸，最终与奎尼酸结合。据我们所知，这是首次报道基于与奎尼酸结合的解毒途径。
