Structural elucidation of T-2 toxin thermal degradation products and investigations toward their occurrence in retail food

J Agric Food Chem. 2009 Mar 11;57(5):1867-75. doi: 10.1021/jf803516s.

Abstract

The stability of T-2 toxin under the conditions of baking or cooking was investigated using heating experiments with the model substances alpha-d-glucose, alpha-d-methyl-glucopyranosid, N-alpha-acetyl-l-lysine methyl ester, and N-alpha-acetyl-cysteine methyl ester. The reaction residue was screened for degradation products using gas chromatography-mass spectrometry (GC-MS) and high-performance liquid chromatography with evaporative light-scattering detection (HPLC-ELSD). Although T-2 toxin was degraded under all conditions, only heating of T-2 toxin with alpha-d-glucose produced a mixture of three degradation products, which were isolated and identified by MS and nuclear magnetic resonance (NMR) experiments. The reaction mechanism for the formation of the T-2 degradation products was elucidated by quantum chemical calculations. The relevance of these degradation products was investigated by baking experiments as well as the analysis of retail food samples. In cell-culture studies using immortalized human kidney epithelial (IHKE) cells, the T-2 degradation products were less cytotoxic (formazan dye cytotoxicity assay) compared to T-2 toxin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line
  • Drug Stability
  • Food Analysis*
  • Humans
  • Molecular Structure
  • Spectrometry, Mass, Electrospray Ionization
  • T-2 Toxin / chemistry*
  • T-2 Toxin / toxicity

Substances

  • T-2 Toxin