Synthesis of deoxynivalenol-3-β-D-O-glucuronide for its use as biomarker for dietary deoxynivalenol exposure

World Mycotoxin Journal

Volumn 5, Issue 2, 2012, Pages 127-132

  Fruhmann, P ^a   Warth, B ^b   Hametner, C ^a   Berthiller, F ^b,c   Horkel, E ^a   Adam, G ^c   Sulyok, M ^b   Krska, R ^b   Frohlich J ^a  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

^b UNIVERSITY OF NATURAL RESOURCES AND LIFE SCIENCES   (Austria)

^c UNIVERSITY OF NATURAL RESOURCES AND LIFE SCIENCES   (Austria)

Author keywords

detoxification; glucuronidation; glycoconjugate; phase II metabolite; urine

Indexed keywords

BIOLOGICAL MARKER; GLUCURONIC ACID; GLUCURONIDE; VOMITOXIN;

ARTICLE; DIETARY INTAKE; GLUCURONIDATION; HYDROLYSIS; LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TANDEM MASS SPECTROMETRY;

ANIMALIA;

EID: 84861524992     PISSN: 18750710     EISSN: 18750796     Source Type: Journal    
DOI: 10.3920/WMJ2011.1366     Document Type: Article

References (15)

1. Berthiller, F., Dall'Asta, C., Schuhmacher, R., Lemmens, M., Adam, G. and Krska, R., 2005. Masked mycotoxins: determination of a deoxynivalenol glucoside in artificially and naturally contaminated wheat by liquid chromatography- tandem mass spectrometry. Journal of Agricultural and Food Chemistry 53: 3421-3425.
2. Coutant, C. and Jacquinet, J.-C., 1995. 2-deoxy-2-trichloroacetamido- D-glucopyranose derivatives in oligosaccharide synthesis: from hyaluronic acid to chondroitin 4-sulfate trisaccharides. Journal of the Chemical Society, Perkin Transactions 1: 1573-1581.
3. Lattanzio, V.M.T., Solfrizzo, M., De Girolamo, A., Chulze, S.N., Torres, A.M. and Visconti, A., 2011. LC-MS/MS characterization of the urinary excretion profile of the mycotoxin deoxynivalenol in human and rat. Journal of Chromatography B 879: 707-715.
4. Levsen, K., Schiebel, H.-M., Behnke, B., Dötzer, R., Dreher, W., Elend, M. and Thiele, H., 2005. Structure elucidation of phase II metabolites by tandem mass spectrometry: an overview. Journal of Chromatography A 1067: 55-72.
5. Meky, F.A., Turner, P.C., Ashcroft, A.E., Miller, J.D., Qiao, Y.L., Roth, M.J. and Wild, C.P., 2003. Development of a urinary biomarker of human exposure to deoxynivalenol. Food and Chemical Toxicology 41: 265-273.
6. Pestka, J.J., 2010. Toxicological mechanisms and potential health effects of deoxynivalenol and nivalenol. World Mycotoxin Journal 3: 323-347.
7. Poppenberger, B., Berthiller, F., Lucyshyn, D., Sieberer, T., Schuhmacher, R., Krska, R., Kuchler, K., Glössl, J., Luschnig, C. and Adam, G., 2003. Detoxification of the Fusarium mycotoxin deoxynivalenol by a UDP-glucosyltransferase from Arabidopsis thaliana. Journal of Biological Chemistry 278: 47905-47914.
8. Pravdic, N. and Keglevic, D., 1964. D-Glucuronic esters. I. Synthesis of methyl 2,3,4-tri-O-acetyl-1-O-acyl-D-glucopyranuronates by use of carbodiimide. Journal of the Chemical Society 1964: 4633-4635.
9. Scientific Committee on Food (SCF), 2002. Opinion of the scientific committee on food on Fusarium toxins. Part 6: group evaluation of T-2 toxin, HT-2 toxin, nivalenol and deoxynivalenol. Scientific Committee on Food (SCF) SCF/CS/CNTM/MYC/27 Final. Available at: http://ec.europa.eu/food/fs/sc/scf/ out123-en.pdf.
10. Stachulski, A.V. and Jenkins, G.N., 1998. The synthesis of O-glucuronides. Natural Products Report 15: 173-186.
11. Turner, P.C., Rothwell, J.A., White, K.L., Gong, Y., Cade, J.E. and Wild, C.P., 2008. Urinary deoxynivalenol is correlated with cereal intake in individuals from the United Kingdom. Environmental Health Perspectives 116: 21-25.
12. Turner, P.C., Taylor, E.F., White, K.L.M., Cade, J.E. and Wild, C.P., 2009. A comparison of 24 h urinary deoxynivalenol with recent v. average cereal consumption for UK adults. British Journal of Nutrition 102: 1276-1279.
13. Turner, P.C., White, K.L.M., Burley, V.J., Hopton, R.P., Rajendram, A., Fisher, J., Cade, J.E. and Wild, C.P., 2010. A comparison of deoxynivalenol intake and urinary deoxynivalenol in UK adults. Biomarkers 15: 553-562.
14. Warth, B., Sulyok, M., Berthiller, F., Schuhmacher, R., Fruhmann, P., Hametner, C., Adam, G., Fröhlich, J. and Krska, R., 2011. Direct quantification of deoxynivalenol glucuronide in human urine as biomarker of exposure to the Fusarium mycotoxin deoxynivalenol. Analytical and Bioanalytical Chemistry 401: 195-200.
15. Wu, X., Murphy, P., Cunnick, J. and Hendrich, S., 2007. Synthesis and characterization of deoxynivalenol glucuronide: its comparative immunotoxicity with deoxynivalenol. Food and Chemical Toxicology 45: 1846-1855.