Profiling of mercapturic acids of acrolein and acrylamide in human urine after consumption of potato crisps*

Molecular Nutrition and Food Research

Volumn 56, Issue 12, 2012, Pages 1825-1837

  Watzek, Nico ^a   Scherbl, Denise ^a   Feld, Julia ^a   Berger, Franz ^a   Doroshyenko, Oxana ^b   Fuhr, Uwe ^b   Tomalik Scharte, Dorota ^b   Baum, Matthias ^a   Eisenbrand, Gerhard ^a   Richling, Elke ^a  

^a Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

^b UNIVERSITY OF COLOGNE   (Germany)

Author keywords

Acrolein; Acrylamide; Glycidamide; Heat induced toxicants; Mercapturic acids

Indexed keywords

ACETYLCYSTEINE; ACROLEIN; ACRYLAMIDE; BIOLOGICAL MARKER; CREATININE; ISOTOPE;

ADULT; ARTICLE; CHEMISTRY; COOKING; FOOD CONTAMINATION; HEAT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; MALE; MASS FRAGMENTOGRAPHY; METHODOLOGY; POTATO; TANDEM MASS SPECTROMETRY; URINE;

ACETYLCYSTEINE; ACROLEIN; ACRYLAMIDE; ADULT; BIOLOGICAL MARKERS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COOKING; CREATININE; FOOD CONTAMINATION; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HOT TEMPERATURE; HUMANS; ISOTOPES; MALE; SOLANUM TUBEROSUM; TANDEM MASS SPECTROMETRY;

SOLANUM TUBEROSUM;

EID: 84870676774     PISSN: 16134125     EISSN: 16134133     Source Type: Journal    
DOI: 10.1002/mnfr.201200323     Document Type: Article

References (55)

1. Zyzak, D. V., Sanders, R. A., Stojanovic, M., Tallmadge, D. H. et al., Acrylamide formation mechanism in heated foods. J. Agric. Food Chem. 2003, 51, 4782-4787.
2. Boon, P. E., de Mul, A., van der Voet, H., van Donkersgoed, G. et al., Calculations of dietary exposure to acrylamide. Mutat. Res. 2005, 580, 143-155.
3. Smith, C. J., Perfetti, T. A., Mullens, M. A., Rodgman, A. et al., "IARC group 2A Carcinogens" reported in cigarette mainstream smoke. Food Chem. Toxicol. 2000, 38, 825-848.
4. O'Brien, J., Renwick, A. G., Constable, A., Dybing, E. et al., Approaches to the risk assessment of genotoxic carcinogens in food: a critical appraisal. Food Chem. Toxicol. 2006, 44, 1613-1635.
5. JECFA, 72. Meeting, Joint FAO/WHO Expert Committee on Food Additives, Rome 2010.
6. EFSA, Results on acrylamide levels in food from monitoring years 2007-2009 and exposure assessment. EFSA J. 2011, 9, 48.
7. Barlow, S., Renwick, A. G., Kleiner, J., Bridges, J. W. et al., Risk assessment of substances that are both genotoxic and carcinogenic report of an International Conference organized by EFSA and WHO with support of ILSI Europe. Food Chem. Toxicol. 2006, 44, 1636-1650.
8. Segerback, D., Calleman, C. J., Schroeder, J. L., Costa, L. G. et al., Formation of N-7-(2-carbamoyl-2-hydroxyethyl)guanine in DNA of the mouse and the rat following intraperitoneal administration of [14C]acrylamide. Carcinogenesis 1995, 16, 1161-1165.
9. Baum, M., Fauth, E., Fritzen, S., Herrmann, A. et al., Acrylamide and glycidamide: approach towards risk assessment based on biomarker guided dosimetry of genotoxic/mutagenic effects in human blood. Adv. Exp. Med. Biol. 2005, 561, 77-88.
10. Puppel, N., Tjaden, Z., Fueller, F., Marko, D., DNA strand breaking capacity of acrylamide and glycidamide in mammalian cells. Mutat. Res. 2005, 580, 71-80.
11. Thielen, S., Baum, M., Hoffmann, M., Loeppky, R. N. et al., Genotoxicity of glycidamide in comparison to (+/-)-anti-benzo[a]pyrene-7, 8-dihydrodiol-9, 10-epoxide and alpha-acetoxy-N-nitroso-diethanolamine in human blood and in mammalian V79-cells. Mol. Nutr. Food Res. 2006, 50, 430-436.
12. Sumner, S. C., Fennell, T. R., Moore, T. A., Chanas, B. et al., Role of cytochrome P450 2E1 in the metabolism of acrylamide and acrylonitrile in mice. Chem. Res. Toxicol. 1999, 12, 1110-1116.
13. Gamboa da Costa, G., Churchwell, M. I., Hamilton, L. P., Von Tungeln, L. S. et al., DNA adduct formation from acrylamide via conversion to glycidamide in adult and neonatal mice. Chem. Res. Toxicol. 2003, 16, 1328-1337.
14. Doerge, D. R., Young, J. F., McDaniel, L. P., Twaddle, N. C. et al., Toxicokinetics of acrylamide and glycidamide in Fischer 344 rats. Toxicol. Appl. Pharmacol. 2005, 208, 199-209.
15. Watzek, N., Bohm, N., Feld, J., Scherbl, D. et al., N7-glycidamide-guanine DNA adduct formation by orally ingested acrylamide in rats: a dose-response study encompassing human diet-related exposure levels. Chem. Res. Toxicol. 2012, 25, 381-390.
16. Fuhr, U., Boettcher, M. I., Kinzig-Schippers, M., Weyer, A. et al., Toxicokinetics of acrylamide in humans after ingestion of a defined dose in a test meal to improve risk assessment for acrylamide carcinogenicity. Cancer Epidemiol. Biomarkers Prev. 2006, 15, 266-271.
17. Boettcher, M. I., Bolt, H. M., Drexler, H., Angerer, J., Excretion of mercapturic acids of acrylamide and glycidamide in human urine after single oral administration of deuterium-labelled acrylamide. Arch. Toxicol. 2006, 80, 55-61.
18. Berger, F. I., Feld, J., Bertow, D., Eisenbrand, G. et al., Biological effects of acrylamide after daily ingestion of various foods in comparison to water: a study in rats. Mol. Nutr. Food Res. 2011, 55, 387-399.
19. Stevens, J. F., Maier, C. S., Acrolein: sources, metabolism, and biomolecular interactions relevant to human health and disease. Mol. Nutr. Food Res. 2008, 52, 7-25.
20. Lane, R. H., Smathers, J. L., Monitoring aldehyde production during frying by reversed-phase liquid chromatography. J. Assoc. Off. Anal. Chem. 1991, 74, 957-960.
21. SKLM, Toxicological Evaluation of a, b-Unsaturated Aliphatic Aldehydes in Foodstuffs, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 2005, pp. 203-217.
22. Medina-Navarro, R., Duran-Reyes, G., Diaz-Flores, M., Hicks, J. J. et al., Glucose-stimulated acrolein production from unsaturated fatty acids. Hum. Exp. Toxicol. 2004, 23, 101-105.
23. Becalski, A., Lau, B. P., Lewis, D., Seaman, S. W., Acrylamide in foods: occurrence, sources, and modeling. J. Agric. Food Chem. 2003, 51, 802-808.
24. Tareke, E., Lyn-Cook, B., Robinson, B., Ali, S. F., Acrylamide: a dietary carcinogen formed in vivo? J. Agric. Food Chem. 2008, 56, 6020-6023.
25. Osorio, V. M., de Lourdes Cardeal, Z., Determination of acrolein in french fries by solid-phase microextraction gas chromatography and mass spectrometry. J. Chromatogr. A 2011, 1218, 3332-3336.
26. Sauvageot, N., Gouffi, K., Laplace, J. M., Auffray, Y., Glycerol metabolism in Lactobacillus collinoides: production of 3-hydroxypropionaldehyde, a precursor of acrolein. Int. J. Food Microbiol. 2000, 55, 167-170.
27. Feron, V. J., Til, H. P., de Vrijer, F., Woutersen, R. A. et al., Aldehydes: occurrence, carcinogenic potential, mechanism of action and risk assessment. Mutat. Res. 1991, 259, 363-385.
28. Roemer, E., Stabbert, R., Rustemeier, K., Veltel, D. J. et al., Chemical composition, cytotoxicity and mutagenicity of smoke from US commercial and reference cigarettes smoked under two sets of machine smoking conditions. Toxicology 2004, 195, 31-52.
29. Nam, D. T., Arseneault, M., Murthy, V., Ramassamy, C., Potential role of acrolein in neurodegeneration and in Alzheimer's disease. Curr. Mol. Pharmacol. 2010, 3, 66-78.
30. Eder, E., Henschler, D., Neudecker, T., Mutagenic properties of allylic and alpha, beta-unsaturated compounds: consideration of alkylating mechanisms. Xenobiotica 1982, 12, 831-848.
31. Yang, I. Y., Chan, G., Miller, H., Huang, Y. et al., Mutagenesis by acrolein-derived propanodeoxyguanosine adducts in human cells. Biochemistry 2002, 41, 13826-13832.
32. Lutz, D., Eder, E., Neudecker, T., Henschler, D., Structure-mutagenicity relationship in α, ß-unsaturated carbonylic compounds and their corresponding allylic alcohols. Mutat. Res. 1982, 93, 305-315.
33. Cohen, S. M., Garland, E. M., St John, M., Okamura, T. et al., Acrolein initiates rat urinary bladder carcinogenesis. Cancer Res. 1992, 52, 3577-3581.
34. Parent, R. A., Caravello, H. E., Hoberman, A. M., Reproductive study of acrolein on two generations of rats. Fundam. Appl. Toxicol. 1992, 19, 228-237.
35. International Agency for Research on Cancer (IARC), Acrolein. Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Humans 1995, Vol. 63. World Health Organization, Lyon, France, pp. 337-372.
36. DFG, Deutsche Forschungsgemeinschaft: MAK und BAT-Werte Liste 2011, Senatskommision zur Prüfung gesundheitsschädlicher Arbeitsstoffe, Mitteilung, p. 47.
37. Chung, F. L., Young, R., Hecht, S. S., Formation of cyclic 1, N2-propanodeoxyguanosine adducts in DNA upon reaction with acrolein or crotonaldehyde. Cancer Res. 1984, 44, 990-995.
38. Zhang, S., Villalta, P. W., Wang, M., Hecht, S. S., Detection and quantitation of acrolein-derived 1, N2-propanodeoxyguanosine adducts in human lung by liquid chromatography-electrospray ionization-tandem mass spectrometry. Chem. Res. Toxicol. 2007, 20, 565-571.
39. Nath, R. G., Ocando, J. E., Guttenplan, J. B., Chung, F. L., 1, N2-propanodeoxyguanosine adducts: potential new biomarkers of smoking-induced DNA damage in human oral tissue. Cancer Res. 1998, 58, 581-584.
40. Gomes, R., Meek, M. E., Eggleton, M., Concise International Chemical Assessment Document No. 43: Acrolein. World Health Organization, Geneva 2002.
41. Tirumalai, R., Rajesh Kumar, T., Mai, K. H., Biswal, S., Acrolein causes transcriptional induction of phase II genes by activation of Nrf2 in human lung type II epithelial (A549) cells. Toxicol. Lett. 2002, 132, 27-36.
42. Parent, R. A., Caravello, H. E., Sharp, D. E., Metabolism and distribution of [2, 3-14C]acrolein in Sprague-Dawley rats. J. Appl. Toxicol. 1996, 16, 449-457.
43. Sanduja, R., Ansari, G. A., Boor, P. J., 3-Hydroxy-propylmercapturic acid: a biologic marker of exposure to allylic and related compounds. J. Appl. Toxicol. 1989, 9, 235-238.
44. Carmella, S. G., Chen, M., Zhang, Y., Zhang, S. et al., Quantitation of acrolein-derived (3-hydroxypropyl)mercapturic acid in human urine by liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry: effects of cigarette smoking. Chem. Res. Toxicol. 2007, 20, 986-990.
45. Schettgen, T., Musiol, A., Kraus, T., Simultaneous determination of mercapturic acids derived from ethylene oxide (HEMA), propylene oxide (2-HPMA), acrolein (3-HPMA), acrylamide (AAMA) and N, N-dimethylformamide (AMCC) in human urine using liquid chromatography/tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2008, 22, 2629-2638.
46. Ewert, A., Granvogl, M., Schieberle, P., Development of two stable isotope dilution assays for the quantitation of acrolein in heat-processed fats. J. Agric. Food Chem. 2011, 59, 3582-3589.
47. Boettcher, M. I., Angerer, J., Determination of the major mercapturic acids of acrylamide and glycidamide in human urine by LC-ESI-MS/MS. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2005, 824, 283-294.
48. Doroshyenko, O., Fuhr, U., Kunz, D., Frank, D. et al., In vivo role of cytochrome P450 2E1 and glutathione-S-transferase activity for acrylamide toxicokinetics in humans. Cancer Epidemiol. Biomarkers Prev. 2009, 18, 433-443.
49. Irwin, R. D., NTP technical report on the comparative toxicity studies of allyl acetate (CAS No. 591-87-7), allyl alcohol (CAS No. 107-18-6) and acrolein (CAS No. 107-02-8) administered by gavage to F344/N rats and B6C3F1 mice. Toxic. Rep. Ser. 2006, 1-73, A71-H10.
50. Mazzachi, B. C., Peake, M. J., Ehrhardt, V., Reference range and method comparison studies for enzymatic and Jaffe creatinine assays in plasma and serum and early morning urine. Clin. Lab. 2000, 46, 53-55.
51. Pan, J., Chung, F. L., Formation of cyclic deoxyguanosine adducts from omega-3 and omega-6 polyunsaturated fatty acids under oxidative conditions. Chem. Res. Toxicol. 2002, 15, 367-372.
52. Ding, Y. S., Blount, B. C., Valentin-Blasini, L., Applewhite, H. S. et al., Simultaneous determination of six mercapturic acid metabolites of volatile organic compounds in human urine. Chem. Res. Toxicol. 2009, 22, 1018-1025.
53. Cheng, G., Wang, M., Villalta, P. W., Hecht, S. S., Detection of 7-(2'-carboxyethyl)guanine but not 7-carboxymethylguanine in human liver DNA. Chem. Res. Toxicol. 2010, 23, 1089-1096.
54. Abraham, K., Andres, S., Palavinskas, R., Berg, K. et al., Toxicology and risk assessment of acrolein in food. Mol. Nutr. Food Res. 2011, 55, 1277-1290.
55. Schwobel, J. A., Wondrousch, D., Koleva, Y. K., Madden, J. C. et al., Prediction of Michael-type acceptor reactivity toward glutathione. Chem. Res. Toxicol. 2010, 23, 1576-1585.