In vitro glucuronidation kinetics of deoxynivalenol by human and animal microsomes and recombinant human UGT enzymes

Archives of Toxicology

Volumn 89, Issue 6, 2015, Pages 949-960

  Maul, Ronald ^a,b   Warth, Benedikt ^c   Schebb, Nils Helge ^d   Krska, Rudolf ^c   Koch, Matthias ^a   Sulyok, Michael ^c  

^a BAM FEDERAL INSTITUTE FOR MATERIALS RESEARCH AND TESTING   (Germany)

^b Inst Veg Orn Crops G Erfurt   (Germany)

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

^d UNIVERSITY OF VETERINARY MEDICINE HANNOVER   (Germany)

Author keywords

Deoxynivalenol; Glucuronidation; Human recombinant UGT; Phase II metabolism; Trichothecene; Uridine diphosphoglucuronyltransferases (UGT)

Indexed keywords

GLUCURONIDE; GLUCURONOSYLTRANSFERASE; RECOMBINANT PROTEIN; TRICHOTHECENE DERIVATIVE; UGT2B4 PROTEIN, HUMAN; VOMITOXIN;

ANIMAL; BOVINE; CARP; DRUG EFFECTS; GENETICS; HUMAN; IN VITRO STUDY; KINETICS; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; METABOLISM; PIG; RAT; SALMONINE; SPECIES DIFFERENCE; TANDEM MASS SPECTROMETRY; XENOBIOTIC METABOLISM;

ANIMALS; CARPS; CATTLE; CHROMATOGRAPHY, LIQUID; GLUCURONIDES; GLUCURONOSYLTRANSFERASE; HUMANS; IN VITRO TECHNIQUES; KINETICS; METABOLIC DETOXICATION, PHASE II; MICROSOMES, LIVER; RATS; RECOMBINANT PROTEINS; SPECIES SPECIFICITY; SWINE; TANDEM MASS SPECTROMETRY; TRICHOTHECENES; TROUT;

EID: 84939879411     PISSN: 03405761     EISSN: 14320738     Source Type: Journal    
DOI: 10.1007/s00204-014-1286-7     Document Type: Article

References (34)

1. Abia WA, Warth B, Sulyok M et al (2013) Bio-monitoring of mycotoxin exposure in Cameroon using a urinary multi-biomarker approach. Food Chem Toxicol 62:927–934. doi:10.1016/j.fct.2013.10.003
2. Barre L, Fournel-Gigleux S, Finel M, Netter P, Magdalou J, Ouzzine M (2007) Substrate specificity of the human UDP-glucuronosyltransferase UGT2B4 and UGT2B7. FEBS J 274(5):1256–1264. doi:10.1111/j.1742-4658.2007.05670.x
3. Berthiller F, Crews C, Dall'Asta C et al (2013) Masked mycotoxins: a review. Mol Nutr Food Res 57(1):165–186. doi:10.1002/mnfr.201100764
4. Bocquet-Appel J-P, Naji S, Vander Linden M, Kozlowski J (2012) Understanding the rates of expansion of the farming system in Europe. J Archaeol Sci 39(2):531–546. doi:10.1016/j.jas.2011.10.010
5. Coffman BL, Rios GR, King CD, Tephly TR (1997) Human UGT2B7 catalyzes morphine glucuronidation. Drug Metab Dispos 25(1):1–4
6. De Boevre M, Di Mavungu JD, Landschoot S et al (2012) Natural occurrence of mycotoxins and their masked forms in food and feed products. World Mycotox J 5(3):207–219. doi:10.3920/wmj2012.1410
7. EC (2007) Commission Regulation (EC) No 1126/2007. Off J L 255:14–17
8. Fruhmann P, Warth B, Hametner C et al (2012) Synthesis of deoxynivalenol-3-β-D-O-glucuronide for its use as biomarker for dietary deoxynivalenol exposure. World Mycotox J 5(2):127–132. doi:10.3920/WMJ2011.1366
9. King CD, Rios GR, Green MD, Tephly TR (2000) UDP-glucuronosyltransferases. Curr Drug Metab 1(2):143–161
10. Lake BG (1987) Preparation and characterization of microsomal fractions for studies on xenobiotic metabolism. In: Snell K, Mullock B, Biochemical toxicology: a practical approach, pp 183–215
11. Luo C-F, Cai B, Hou N et al (2012) UDP-glucuronosyltransferase 1A1 is the principal enzyme responsible for puerarin metabolism in human liver microsomes. Arch Toxicol 86(11):1681–1690. doi:10.1007/s00204-012-0874-7
12. Ma YY, Guo HW (2008) Mini-review of studies on the carcinogenicity of deoxynivalenol. Environ Toxicol Pharmacol 25(1):1–9. doi:10.1016/j.etap.2007.09.007
13. Maul R, Müller C, Rieß S, Koch M, Methner FJ, Nehls I (2012a) Germination induces the glucosylation of the Fusarium mycotoxin deoxynivalenol in various grains. Food Chem 131(1):274–279
14. Maul R, Warth B, Kant J-S et al (2012b) Investigation of the hepatic glucuronidation pattern of the fusarium mycotoxin deoxynivalenol in various species. Chem Res Toxicol 25(12):2715–2717. doi:10.1021/tx300348x
15. Nagl V, Schwartz H, Krska R et al (2012) Metabolism of the masked mycotoxin deoxynivalenol-3-glucoside in rats. Toxicol Lett 213(3):367–373
16. Nakamura A, Nakajima M, Yamanaka H, Fujiwara R, Yokoi T (2008) Expression of UGT1A and UGT2B mRNA in human normal tissues and various cell lines. Drug Metab Dispos 36(8):1461–1464. doi:10.1124/dmd.108.021428
17. Ohno S, Nakajin S (2009) Determination of mRNA expression of human UDP-glucuronosyltransferases and application for localization in various human tissues by real-time reverse transcriptase-polymerase chain reaction. Drug Metab Dispos 37(1):32–40. doi:10.1124/dmd.108.023598
18. Pestka JJ (2007) Deoxynivalenol: toxicity, mechanisms and animal health risks. Anim Feed Sci Technol 137(3–4):283–298
19. Pestka J (2010) Deoxynivalenol: mechanisms of action, human exposure, and toxicological relevance. Arch Toxicol 84(9):663–679. doi:10.1007/s00204-010-0579-8
20. Ritter JK (2000) Roles of glucuronidation and UDP-glucuronosyltransferases in xenobiotic bioactivation reactions. Chem Biol Interact 129(1–2):171–193. doi:10.1016/S0009-2797(00)00198-8
21. Rocha O, Ansari K, Doohan FM (2005) Effects of trichothecene mycotoxins on eukaryotic cells: a review. Food Addit Contam 22(4):369–378. doi:10.1080/02652030500058403
22. Šarkanj B, Warth B, Uhlig S et al (2013) Urinary analysis reveals high deoxynivalenol exposure in pregnant women from Croatia. Food Chem Toxicol 62:231–237. doi:10.1016/j.fct.2013.08.043
23. 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 (adopted by the SCF on 26 February 2002). http://ec.europa.eu/food/fs/sc/scf/out123_en.pdf
24. Shephard GS, Burger H-M, Gambacorta L et al (2013) Multiple mycotoxin exposure determined by urinary biomarkers in rural subsistence farmers in the former Transkei, South Africa. Food Chem Toxicol 62:217–225. doi:10.1016/j.fct.2013.08.040
25. Sneitz N, Vahermo M, Mosorin J, Laakkonen L, Poirier D, Finel M (2013) Regiospecificity and stereospecificity of human UDP-glucuronosyltransferases in the glucuronidation of estriol, 16-epiestriol, 17-epiestriol, and 13-epiestradiol. Drug Metab Dispos 41(3):582–591. doi:10.1124/dmd.112.049072
26. Stone AN, Mackenzie PI, Galetin A, Houston JB, Miners JO (2003) Isoform selectivity and kinetics of morphine 3- and 6-glucuronidation by human UDP-glucuronosyltransferases: evidence for atypical glucuronidation kinetics by UGT2B7. Drug Metab Dispos 31(9):1086–1089. doi:10.1124/dmd.31.9.1086
27. Turner PC, Hopton RP, White KLM, Fisher J, Cade JE, Wild CP (2011) Assessment of deoxynivalenol metabolite profiles in UK adults. Food Chem Toxicol 49(1):132–135. doi:10.1016/j.fct.2010.10.007
28. Uhlig S, Ivanova L, Fæste CK (2013) Enzyme-assisted synthesis and structural characterization of the 3-, 8-, and 15-glucuronides of deoxynivalenol. J Agric Food Chem 61(8):2006–2012. doi:10.1021/jf304655d
29. Varga E, Malachova A, Schwartz H, Krska R, Berthiller F (2012) Survey of deoxynivalenol and its conjugates deoxynivalenol-3-glucoside and 3-acetyl-deoxynivalenol in 374 beer samples. Food Addit Contam Part A:1–10. doi:10.1080/19440049.2012.726745
30. Veršilovskis A, Geys J, Huybrechts B, Goossens E, De Saeger S, Callebaut A (2012) Simultaneous determination of masked forms of deoxynivalenol and zearalenone after oral dosing in rats by LC-MS/MS. World Mycotox J 5(3):303–318. doi:10.3920/wmj2012.1411
31. Warth B, Sulyok M, Fruhmann P et al (2012a) Assessment of human deoxynivalenol exposure using an LC–MS/MS based biomarker method. Toxicol Lett 211(1):85–90. doi:10.1016/j.toxlet.2012.02.023
32. Warth B, Sulyok M, Fruhmann P et al (2012b) Development and validation of a rapid multi-biomarker liquid chromatography/tandem mass spectrometry method to assess human exposure to mycotoxins. Rapid Commun Mass Spectrom 26(13):1533–1540. doi:10.1002/rcm.6255
33. Warth B, Sulyok M, Berthiller F, Schuhmacher R, Krska R (2013) New insights into the human metabolism of the Fusarium mycotoxins deoxynivalenol and zearalenone. Toxicol Lett 220(1):88–94. doi:10.1016/j.toxlet.2013.04.012
34. Yang W, Yu M, Fu J et al (2014) Deoxynivalenol induced oxidative stress and genotoxicity in human peripheral blood lymphocytes. Food Chem Toxicol 64:383–396. doi:10.1016/j.fct.2013.12.012