Reaction of (conjugated) deoxynivalenol with sulphur reagents - novel metabolites, toxicity and application

Abstract

Recently, three novel deoxynivalenol (DON) sulphonates (DONS-1, -2 and -3) formed by transformation of DON with sulphur reagents were discovered. Their structures were elucidated, factors influencing their formation were investigated and their stability was evaluated. The first aim of the present work was to assess the toxicity of the three DONS. The hypothesis was a loss of toxicity of DONS-1 and reduced toxicity of DONS-2 and DONS-3 compared with DON. Three different toxicity tests confirmed this hypothesis, revealing reduction of toxicity by factors of at least 330, 29 and 33 for DONS-1, -2 and -3, respectively. The second objective was to investigate the reaction of DON conjugates with sulphur reagents both in solution and in cereal samples, and to determine the pattern of the formed DONS in DON-contaminated cereals. Reversed phase ultra high performance liquid chromatography-high resolution tandem mass spectrometry demonstrated that also conjugated mycotoxins (DON-3-glucoside, 3-acetyl-DON, 15-acetyl-DON) are converted into DON conjugate sulphonates upon incubation with sodium metabisulphite (SBS) or sodium sulphite in solution. DON conjugate sulphonates of the series 1, 2 and 3 differed in their fragmentation pattern in a similar way as DONS-1, -2 and -3. Treatment of a barley sample contaminated with DON, 3-acetyl-DON and the masked mycotoxin DON-3-glucoside with SBS revealed that the predominantly formed compounds are DONS-3 and DON conjugate sulphonates of the series 3, followed by those of the series 2. Incubation of DON containing maize samples of different moisture contents with 0.5% of SBS or sodium sulphite for 7 days confirmed DONS-3 as main DON transformation product. Both in barley and in maize, SBS and sodium sulphite showed different efficiency for transformation of DON at low moisture contents. These findings provide novel insights into inactivation of DON-contaminated cereals.