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Glucosylation of T-2 and HT-2 toxins using biotransformation and chemical synthesis: Preparation, stereochemistry, and stability
- Source :
- Mycotoxin Research
- Publication Year :
- 2018
- Publisher :
- Springer Science and Business Media LLC, 2018.
-
Abstract
- Plant-derived phase II metabolites of T-2 toxin (T2) and HT-2 toxin (HT2) were first described in 2011 and further characterized in the following years. Since then, some efforts have been made to understand their biosynthesis, occurrence, toxicity, toxicokinetics, and finally relevance for consumers. Thus, the probably most important question is whether and how these metabolites contribute to toxicity upon hydrolysis either during food processing or the gastrointestinal passage. To answer this question, firstly, knowledge on the correct stereochemistry of T2 and HT2 glucosides is important as this affects hydrolysis and chemical behavior. So far, contradictory results have been published concerning the number and anomericity of occurring glucosides. For this reason, we set up different strategies for the synthesis of mg-amounts of T2, HT2, and T2 triol glucosides in both α and ß configuration. All synthesized glucosides were fully characterized by NMR spectroscopy as well as mass spectrometry and used as references for the analysis of naturally contaminated food samples to validate or invalidate their natural occurrence. Generally, 3-O-glucosylation was observed with two anomers of HT2 glucoside being present in contaminated oats. In contrast, only one anomer of T2 glucoside was found. The second aspect of this study addresses the stability of the glucosides during thermal food processing. Oat flour was artificially contaminated with T2 and HT2 glucosides individually and extruded at varying initial moisture content and temperature. All four glucosides appear to be more stable during food extrusion than the parent compounds with the glucosidic bond not being hydrolyzed.
- Subjects :
- 0301 basic medicine
Glucoside
Food processing
Glycosylation
Magnetic Resonance Spectroscopy
Anomer
Avena
Stereochemistry
Food Contamination
HT-2 toxin
Toxicology
01 natural sciences
Microbiology
Chemical synthesis
Mass Spectrometry
03 medical and health sciences
chemistry.chemical_compound
Hydrolysis
Biosynthesis
Biotransformation
Toxicokinetics
Glycosides
Modified mycotoxins
010401 analytical chemistry
0104 chemical sciences
T-2 Toxin
030104 developmental biology
chemistry
Original Article
Triol
Masked mycotoxins
Biotechnology
Subjects
Details
- ISSN :
- 18671632 and 01787888
- Volume :
- 34
- Database :
- OpenAIRE
- Journal :
- Mycotoxin Research
- Accession number :
- edsair.doi.dedup.....6e79396e197e201d2f6bef58251db8f0