102
views
0
recommends
+1 Recommend
0 collections
    0
    shares
      • Record: found
      • Abstract: found
      • Article: not found

      Hydrolytic fate of deoxynivalenol-3-glucoside during digestion

      research-article
      a , * , b , c , d , e , b , f
      Toxicology Letters
      Elsevier
      D3G, deoxynivalenol-3-glucoside, DON, deoxynivalenol, JECFA, Joint FAO/WHO Expert Committee on Food Additives, ZEN, zearalenone, Z-14-G, zearalenone-14-β-d-glucoside, HPLC, high performance liquid chromatography, MS, mass spectrometry, MS/MS, tandem mass spectrometry, EDTA, ethylenediaminetetraacetic acid, EC, Enzyme Commission number, DSMZ, Deutsche Sammlung von Mikroorganismen und Zellkulturen, ATCC, American Type Culture Collection, LMG, Laboratorium voor Microbiologie, ESI, electrospray ionization, CAD, collision activated dissociation, MRM, multiple reaction monitoring, DP, declustering potential, CE, collision energy, hCBG, human cytosolic β-glucosidase, Deoxynivalenol-3-glucoside, Deoxynivalenol, Conjugated mycotoxins, Masked mycotoxins, Digestion, Hydrolysis

      Read this article at

      ScienceOpenPublisherPMC
      Bookmark
          There is no author summary for this article yet. Authors can add summaries to their articles on ScienceOpen to make them more accessible to a non-specialist audience.

          Highlights

          ► Deoxynivalenol-3-glucoside (D3G) is hydrolyzed to deoxynivalenol during digestion. ► D3G is resistant to acids and enzymes expressed by humans. ► D3G is partly cleaved by cellulase and cellobiase. ► Several intestinal bacteria liberate deoxynivalenol from D3G. ► D3G is of toxicological relevance and should be monitored in food.

          Abstract

          Deoxynivalenol-3-β- d-glucoside (D3G), a plant phase II metabolite of the Fusarium mycotoxin deoxynivalenol (DON), occurs in naturally contaminated wheat, maize, oat, barley and products thereof. Although considered as a detoxification product in plants, the toxicity of this substance in mammals is currently unknown. A major concern is the possible hydrolysis of the D3G conjugate back to its toxic precursor mycotoxin DON during mammalian digestion. We used in vitro model systems to investigate the stability of D3G to acidic conditions, hydrolytic enzymes and intestinal bacteria, mimicking different stages of digestion. D3G was found resistant to 0.2 M hydrochloric acid for at least 24 h at 37 °C, suggesting that it will not be hydrolyzed in the stomach of mammals. While human cytosolic β-glucosidase also had no effect, fungal cellulase and cellobiase preparations could cleave a significant portion of D3G. Most importantly, several lactic acid bacteria such as Enterococcus durans, Enterococcus mundtii or Lactobacillus plantarum showed a high capability to hydrolyze D3G. Taken together these data indicate that D3G is of toxicological relevance and should be regarded as a masked mycotoxin.

          Related collections

          Most cited references28

          • Record: found
          • Abstract: found
          • Article: not found

          Detoxification of the Fusarium mycotoxin deoxynivalenol by a UDP-glucosyltransferase from Arabidopsis thaliana.

          Plant pathogenic fungi of the genus Fusarium cause agriculturally important diseases of small grain cereals and maize. Trichothecenes are a class of mycotoxins produced by different Fusarium species that inhibit eukaryotic protein biosynthesis and presumably interfere with the expression of genes induced during the defense response of the plants. One of its members, deoxynivalenol, most likely acts as a virulence factor during fungal pathogenesis and frequently accumulates in grain to levels posing a threat to human and animal health. We report the isolation and characterization of a gene from Arabidopsis thaliana encoding a UDP-glycosyltransferase that is able to detoxify deoxynivalenol. The enzyme, previously assigned the identifier UGT73C5, catalyzes the transfer of glucose from UDP-glucose to the hydroxyl group at carbon 3 of deoxynivalenol. Using a wheat germ extract-coupled transcription/translation system we have shown that this enzymatic reaction inactivates the mycotoxin. This deoxynivalenol-glucosyltransferase (DOGT1) was also found to detoxify the acetylated derivative 15-acetyl-deoxynivalenol, whereas no protective activity was observed against the structurally similar nivalenol. Expression of the glucosyltransferase is developmentally regulated and induced by deoxynivalenol as well as salicylic acid, ethylene, and jasmonic acid. Constitutive overexpression in Arabidopsis leads to enhanced tolerance against deoxynivalenol.
            Bookmark
            • Record: found
            • Abstract: found
            • Article: not found

            Glycosyltransferases of lipophilic small molecules.

            Glycosyltransferases of small molecules transfer sugars to a wide range of acceptors, from hormones and secondary metabolites to biotic and abiotic chemicals and toxins in the environment. The enzymes are encoded by large multigene families and can be identified by a signature motif in their primary sequence, which classifies them as a subset of Family 1 glycosyltransferases. The transfer of a sugar onto a lipophilic acceptor changes its chemical properties, alters its bioactivity, and enables access to membrane transporter systems. In vitro studies have shown that a single gene product can glycosylate multiple substrates of diverse origins; multiple enzymes can also glycosylate the same substrate. These features suggest that in a cellular context, substrate availability is a determining factor in enzyme function, and redundancy depends on the extent of coordinate gene regulation. This review discusses the role of these glycosyltransferases in underpinning developmental and metabolic plasticity during adaptive responses.
              Bookmark
              • Record: found
              • Abstract: found
              • Article: not found

              The ability to detoxify the mycotoxin deoxynivalenol colocalizes with a major quantitative trait locus for Fusarium head blight resistance in wheat.

              We investigated the hypothesis that resistance to deoxynivalenol (DON) is a major resistance factor in the Fusarium head blight (FHB) resistance complex of wheat. Ninety-six double haploid lines from a cross between 'CM-82036' and 'Remus' were examined. The lines were tested for DON resistance after application of the toxin in the ear, and for resistances to initial infection and spread of FHB after artificial inoculation with Fusarium spp. Toxin application to flowering ears induced typical FHB symptoms. Quantitative trait locus (QTL) analyses detected one locus with a major effect on DON resistance (logarithm of odds = 53.1, R2 = 92.6). The DON resistance phenotype was closely associated with an important FHB resistance QTL, Qfhs.ndsu-3BS, which previously was identified as governing resistance to spread of symptoms in the ear. Resistance to the toxin was correlated with resistance to spread of FHB (r = 0.74, P < 0.001). In resistant wheat lines, the applied toxin was converted to DON-3-O-glucoside as the detoxification product. There was a close relation between the DON-3-glucoside/DON ratio and DON resistance in the toxin-treated ears (R2 = 0.84). We conclude that resistance to DON is important in the FHB resistance complex and hypothesize that Qfhs.ndsu-3BS either encodes a DON-glucosyl-transferase or regulates the expression of such an enzyme.
                Bookmark

                Author and article information

                Journal
                Toxicol Lett
                Toxicol. Lett
                Toxicology Letters
                Elsevier
                0378-4274
                1879-3169
                30 October 2011
                30 October 2011
                : 206
                : 3
                : 264-267
                Affiliations
                [a ]Christian Doppler Laboratory for Mycotoxin Metabolism, Center for Analytical Chemistry, Department for Agrobiotechnology (IFA-Tulln), University of Natural Resources and Life Sciences, Vienna (BOKU), Konrad Lorenz Str. 20, 3430 Tulln, Austria
                [b ]Center for Analytical Chemistry, Department for Agrobiotechnology (IFA-Tulln), University of Natural Resources and Life Sciences, Vienna (BOKU), Konrad Lorenz Str. 20, 3430 Tulln, Austria
                [c ]Institute of Food Science, Department of Food Sciences and Technology, University of Natural Resources and Life Sciences, Vienna (BOKU), Muthgasse 18, 1190 Vienna, Austria
                [d ]Christian Doppler Laboratory for Innovative Bran Biorefinery, Department of Food Sciences and Technology, University of Natural Resources and Life Sciences, Vienna (BOKU), Muthgasse 18, 1190 Vienna, Austria
                [e ]Institute of Food Research, Norwich Research Park, Colney Lane, NR4 7UA, United Kingdom
                [f ]Department of Applied Genetics and Cell Biology, University of Natural Resources and Life Sciences, Vienna (BOKU), Konrad Lorenz Str. 24, 3430 Tulln, Austria
                Author notes
                [* ]Corresponding author. Tel.: +43 2272 66280 413; fax: +43 2272 66280 403. franz.berthiller@ 123456boku.ac.at
                Article
                TOXLET7715
                10.1016/j.toxlet.2011.08.006
                3185207
                21878373
                4d17d51d-71c7-4dd9-880d-e372af48a128
                © 2011 Elsevier Ireland Ltd.

                This document may be redistributed and reused, subject to certain conditions.

                History
                : 26 July 2011
                : 11 August 2011
                : 12 August 2011
                Categories
                Article

                Toxicology
                digestion,d3g, deoxynivalenol-3-glucoside,conjugated mycotoxins,don, deoxynivalenol,hplc, high performance liquid chromatography,ms, mass spectrometry,z-14-g, zearalenone-14-β-d-glucoside,mrm, multiple reaction monitoring,dp, declustering potential,hydrolysis,ce, collision energy,deoxynivalenol-3-glucoside,cad, collision activated dissociation,edta, ethylenediaminetetraacetic acid,ms/ms, tandem mass spectrometry,zen, zearalenone,masked mycotoxins,hcbg, human cytosolic β-glucosidase,jecfa, joint fao/who expert committee on food additives,deoxynivalenol,lmg, laboratorium voor microbiologie,ec, enzyme commission number,esi, electrospray ionization,dsmz, deutsche sammlung von mikroorganismen und zellkulturen,atcc, american type culture collection

                Comments

                Comment on this article