Structural elucidation and analysis of thermal degradation products of the Fusarium mycotoxin nivalenol
Autor: | Anja Knecht, Simon Göckler, Michael Bretz, Hans-Ulrich Humpf |
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Rok vydání: | 2005 |
Předmět: |
Fusarium
Spectrometry Mass Electrospray Ionization Hot Temperature Magnetic Resonance Spectroscopy Chemical structure Trichothecene medicine.disease_cause Kidney Gas Chromatography-Mass Spectrometry chemistry.chemical_compound medicine Humans Mycotoxin Cytotoxicity Chromatography High Pressure Liquid Cell Line Transformed Chromatography biology Molecular Structure Toxin Epithelial Cells Mycotoxins biology.organism_classification Embryo Mammalian chemistry Formazan Gas chromatography–mass spectrometry Trichothecenes Food Science Biotechnology |
Zdroj: | Molecular nutritionfood research. 49(4) |
ISSN: | 1613-4125 |
Popis: | The major class of mycotoxins produced by Fusarium moulds are trichothecenes, a large group of sesquiterpenes sharing the same basic chemical structure, a 12,13-epoxytrichothec-9-ene ring system. Their toxic effects range from causing diarrhoea, vomiting and gastro-intestinal inflammation to noncompetitive inhibition of the biosynthesis of proteins in eukaryotic cells. Trichothecenes in general are relatively stable compounds, their degradation is observed only at high temperatures and prolonged heating time. In order to investigate the stability of the trichothecene nivalenol (NIV) under food processing conditions such as cooking or baking, we performed model heating experiments and screened the residue for degradation products using gas chromatography-mass spectrometry (GC-MS). Heating of nivalenol, especially under mild alkaline conditions, gave a mixture of four compounds (norNIV A, norNIV B, norNIV C, and NIV lactone), which where isolated and identified by nuclear magnetic resonance (NMR) and MS experiments. Although their formation was also demonstrated in heating experiments with spiked flour samples, only norNIV B was detectable in a screening of several commercially available samples, possibly due to the very low contamination with nivalenol. Furthermore, cell culture experiments using immortalized human kidney epithelial (IHKE) cells showed that the four compounds are less cytotoxic (formazan dye cytotoxicity assay) compared to nivalenol. Whereas nivalenol revealed an EC50 at 0.9 micromol, all other compounds did not show any significant effect up to 100 micromol. |
Databáze: | OpenAIRE |
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