期刊
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
卷 64, 期 36, 页码 6903-6910出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.jafc.6b02853
关键词
thiol; mycotoxin; HRMS; LC-MS; NMR; ERETIC; conjugation; GSH; GST
资金
- Research Council of Norway [225332, 226244/F50]
- Animalia, Lantmannen Research Foundation
- Felleskjopet Forutvikling
Glutathione (GSH) conjugates of the mycotoxin 4-deoxynivalenol (DON), 1, have been detected in plants by LC-MS, but their identities were not confirmed due to a lack of standards. We have synthesized DON GSH conjugates in alkaline solution, The major products 2 and 5 were isolated and their structures determined by mass spectrometry and NMR spectroscopy as GSH adducts at C-13 and C-10 (via epoxide and Michael addition, respectively) of 1. Other Michael addition products were also tentatively identified by LC-MS. Concentrations of 2 and 5 were determined by quantitative NMR and are suitable for use as quantitative standards for LC-MS studies of plant and animal metabolism of 1. LC-MS showed that in the presence of human glutathione S-transferases of the alpha and mu classes, the reaction of DON and GSH proceeded with half-life of 17 h, identical with the rate of the uncatalyzed reaction rate, indicating an absence of catalysis.
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