[Isolation and structural elucidation of thermal degradation products of theFusarium mycotoxin nivalenol].

The major class of mycotoxins produced byFusarium moulds are trichothecenes, a large group of sesquiterpenes sharing the same basic chemical structure, a 12,13-epoxytrichothec-9-ene ring system. Their toxicity is attributed to their ability to noncompetitively inhibit the biosynthesis of proteins in eukaryotic cells. Trichothecenes in general are relatively stable substances and their degradation is reported only at high temperatures and prolonged heating time.In an attempt to investigate the stability of the trichothecene nivalenol (NIV) under food processing conditions such as cooking or baking, we performed a number of experiments using a model heating system.Heating of nivalenol, especially under mild alkaline conditions, gave a mixture of four compounds (norNIV A, norNIV B, norNIV C and NIV lactone), which were separated and further analyzed by gas chromatography/mass spectrometry (GC/MS) and liquid chromatography/mass spectrometry (LC/MS). Structure elucidation was achieved by 1D and 2D nuclear magnetic resonance (NMR) experiments.We further demonstrated the formation of these products in heating experiments with spiked flour samples. In a screening of several commercially available products only norNIV B was detected in one of the samples, possibly due to the very low contamination of these particular samples with nivalenol.