title: Characterization of three deoxynivalenol sulfonates formed by reaction of deoxynivalenol with sulfur reagents.
abstract: 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.
authors: Christian Doppler Laboratory for Mycotoxin Metabolism and Center for Analytical Chemistry, Department for Agrobiotechnology (IFA-Tulln), University of Natural Resources and Life Sciences, Vienna , Konrad Lorenz Str. 20, 3430 Tulln, Austria.
authors: Heidi Elisabeth
authors: HE
authors: Schwartz
authors: Christian
authors: C
authors: Hametner
authors: Veronika
authors: V
authors: Slavik
authors: Oliver
authors: O
authors: Greitbauer
authors: Gerlinde
authors: G
authors: Bichl
authors: Elisavet
authors: E
authors: Kunz-Vekiru
authors: Dian
authors: D
authors: Schatzmayr
authors: Franz
authors: F
authors: Berthiller
mesh_terms: D000821:Animal Feed / Q000032:analysis*; D005506:Food Contamination / Q000032:analysis; D009183:Mycotoxins / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry*; D053719:Tandem Mass Spectrometry; D014255:Trichothecenes / Q000737:chemistry*
chemical_list: D009183:Mycotoxins; D014255:Trichothecenes; C555344:deoxynivalenol sulfonate; D013455:Sulfur; C007262:deoxynivalenol