Characterization of Three Deoxynivalenol Sulfonates Formed by Reaction of Deoxynivalenol with Sulfur Reagents

• Published in: Journal of agricultural and food chemistry Vol. 61; no. 37; pp. 8941 - 8948
• Main Authors: Schwartz, Heidi Elisabeth, Hametner, Christian, Slavik, Veronika, Greitbauer, Oliver, Bichl, Gerlinde, Kunz-Vekiru, Elisavet, Schatzmayr, Dian, Berthiller, Franz
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 18.09.2013; Amer Chemical Soc
• Subjects: Agriculture; Agriculture, Multidisciplinary; Animal Feed - analysis; Biological and medical sciences; Chemistry; Chemistry, Applied; deoxynivalenol; feeds; Food Contamination - analysis; Food industries; Food Science & Technology; Food toxicology; Fundamental and applied biological sciences. Psychology; Life Sciences & Biomedicine; molecular weight; Mycotoxins - chemistry; nuclear magnetic resonance spectroscopy; Physical Sciences; Science & Technology; sodium bisulfite; sodium metabisulfite; sulfonates; sulfur; Sulfur - chemistry; Tandem Mass Spectrometry; Trichothecenes - chemistry; ultra high performance liquid chromatography−high resolution tandem mass spectrometry; sodium sulfite; sulfur reagents; nuclear magnetic resonance spectroscopy; deoxynivalenol sulfonates; structure elucidation; sodium metabisulfite; ultra high performance liquid chromatography-high resolution tandem mass spectrometry; BISULFITE; WHEAT; DE-EPOXY-DON; CONTAMINATED CORN; REDUCTION; MYCOTOXIN; Sulfites; High resolution; Mycotoxin; Vomitoxin; HPLC chromatography; ultra high performance liquid chromatography―high resolution tandem mass spectrometry; NMR spectrometry; Sulfonate; Characterization; Toxin; Sodium; Mass spectrometry MS/MS; Reagents; Nuclear magnetic resonance; Sulfur; Structure
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf403438b

Reduction of the Fusarium mycotoxin deoxynivalenol (DON) in animal feed by treatment with sodium bisulfite and sodium metabisulfite has been successfully demonstrated in several studies. All of them reported formation of one DON sulfonate of strongly reduced toxicity compared to DON. The starting point of the present work was investigation of different sulfur reagents for reduction of DON. In the course of these experiments, three different DON sulfonates termed DON sulfonate 1 (1), DON sulfonate 2 (2), and DON sulfonate 3 (3) were identified and structurally elucidated by UHPLC–HRMS/MS as well as NMR spectroscopy. Compound 1 is characterized by loss of the epoxide group, and 2 by formation of a hemiketal. Compound 3 is an equilibrating mixture of two isomers, a ketone and a hemiketal. The MS/MS pattern can be used to differentiate the three DON sulfonates, despite their same mass and molecular formula. Investigation of parameters influencing formation and stability of DON sulfonates revealed that rapid formation of 1 and 2 occurs at alkaline pH, whereas at acidic pH, slow formation of 3 takes place, irrespective of the sulfur reagent used. Whereas 1 and 2 are stable across a broad pH range, 3 decomposes to DON, 1, and 2 at alkaline pH. In addition, both 2 and 3 are unstable in solid form. The formation, characterization, and stability of three novel DON sulfonates with respect to results from previous studies are discussed, providing insights of relevance for detoxification of DON-containing animal feed.