Ford Kevin A, Casida John E
Environmental Chemistry and Toxicology Laboratory, Department of Environmental Science, Policy and Management, University of California, Berkeley, California 94720-3112, USA.
J Agric Food Chem. 2008 Nov 12;56(21):10168-75. doi: 10.1021/jf8020909. Epub 2008 Oct 16.
The metabolism of seven commercial neonicotinoid insecticides was compared in spinach seedlings (Spinacia oleracea) using HPLC-DAD and LC-MSD to analyze the large number and great variety of metabolites. The parent neonicotinoid levels in the foliage following hydroponic treatment varied from differences in uptake and persistence. The metabolic reactions included nitro reduction, cyano hydrolysis, demethylation, sulfoxidation, imidazolidine and thiazolidine hydroxylation and olefin formation, oxadiazine hydroxylation and ring opening, and chloropyridinyl dechlorination. The identified phase I plant metabolites were generally the same as those in mammals, but the phase II metabolites differed in the conjugating moieties. Novel plant metabolites were various neonicotinoid-derived O- and N-glucosides and -gentiobiosides and nine amino acid conjugates of chloropyridinylcarboxylic acid. Metabolites known to be active on nicotinic acetylcholine receptors included the desnitro- and descyanoguanidines and olefin derivatives. The findings highlight both metabolites common to several neonicotinoids and those that are compound specific.
利用高效液相色谱-二极管阵列检测法（HPLC-DAD）和液相色谱-质谱检测法（LC-MSD）分析大量且种类繁多的代谢物，比较了七种市售新烟碱类杀虫剂在菠菜幼苗（菠菜）中的代谢情况。水培处理后叶片中母体新烟碱类物质的含量因吸收和持久性的差异而有所不同。代谢反应包括硝基还原、氰基水解、去甲基化、硫氧化、咪唑烷和噻唑烷羟基化以及烯烃形成、恶二嗪羟基化和开环，还有氯吡啶基脱氯。鉴定出的I相植物代谢物通常与哺乳动物中的相同，但II相代谢物在共轭部分有所不同。新型植物代谢物是各种新烟碱类衍生的O-和N-葡萄糖苷及龙胆二糖苷，以及氯吡啶基羧酸的九种氨基酸共轭物。已知对烟碱型乙酰胆碱受体有活性的代谢物包括脱硝基和脱氰胍类以及烯烃衍生物。这些发现突出了几种新烟碱类共有的代谢物以及化合物特有的代谢物。
