The garlic ingredient diallyl sulfide inhibits cytochrome P450 2E1 dependent bioactivation of acrylamide to glycidamide

Toxicology Letters

Volumn 164, Issue 1, 2006, Pages 1-5

  Taubert, Dirk ^a   Glöckner, Reinhild ^b   Müller, Dieter ^b   Schömig, Edgar ^a  

^a UNIVERSITY HOSPITAL OF COLOGNE   (Germany)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

Acrylamide; Cytochrome P450 2E1; Diallyl sulfide; Garlic; Glycidamide; Rat liver slices

Indexed keywords

ACRYLAMIDE; ALLYL SULFIDE; CARCINOGEN; CYTOCHROME P450 2E1; CYTOCHROME P450 INHIBITOR; GLYCIDAMIDE;

ANIMAL TISSUE; ARTICLE; BIOTRANSFORMATION; CONTROLLED STUDY; GARLIC; LIQUID CHROMATOGRAPHY; LIVER SLICE; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; RAT STRAIN; TANDEM MASS SPECTROMETRY;

ACRYLAMIDE; ALLYL COMPOUNDS; ANIMALS; BIOTRANSFORMATION; CYTOCHROME P-450 CYP2E1; EPOXY COMPOUNDS; GARLIC; LIVER; MALE; RATS; RATS, WISTAR; SULFIDES;

ALLIUM SATIVUM; ANIMALIA;

EID: 33646089879     PISSN: 03784274     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxlet.2005.11.004     Document Type: Article

References (45)

1. Adler I.D., Baumgartner A., Gonda H., Friedman M.A., and Skerhut M. 1-Aminobenzotriazole inhibits acrylamide-induced dominant lethal effects in spermatids of male mice. Mutagenesis 15 (2000) 133-136
2. Amagase H., Petesch B.L., Matsuura H., Kasuga S., and Itakura Y. Intake of garlic and its bioactive components. J. Nutr. 131 (2001) 955S-962S
3. Baum M., Fauth E., Fritzen S., Herrmann A., Mertes P., Merz K., Rudolphi M., Zankl H., and Eisenbrand G. Acrylamide and glycidamide: genotoxic effects in V79-cells and human blood. Mutat. Res. 580 (2005) 61-69
4. Besaratinia A., and Pfeifer G.P. Weak yet distinct mutagenicity of acrylamide in mammalian cells. J. Natl. Cancer Inst. 95 (2003) 889-896
5. Boettcher M.I., Schettgen T., Kutting B., Pischetsrieder M., and Angerer J. Mercapturic acids of acrylamide and glycidamide as biomarkers of the internal exposure to acrylamide in the general population. Mutat. Res. 580 (2005) 167-176
6. Boon P.E., de Mul A., van der Voet H., van Donkersgoed G., Brette M., and van Klaveren J.D. Calculations of dietary exposure to acrylamide. Mutat. Res. 580 (2005) 143-155
7. Brady J.F., Li D.C., Ishizaki H., and Yang C.S. Effect of diallyl sulfide on rat liver microsomal nitrosamine metabolism and other monooxygenase activities. Cancer Res. 48 (1988) 5937-5940
8. Brady J.F., Ishizaki H., Fukuto J.M., Lin M.C., Fadel A., Gapac J.M., and Yang C.S. Inhibition of cytochrome P-450 2E1 by diallyl sulfide and its metabolites. Chem. Res. Toxicol. 4 (1991) 642-647
9. Calleman C.J. The metabolism and pharmacokinetics of acrylamide: implications for mechanisms of toxicity and human risk estimation. Drug Metab. Rev. 28 (1996) 527-590
10. Doerge D.R., Young J.F., McDaniel L.P., Twaddle N.C., and Churchwell M.I. Toxicokinetics of acrylamide and glycidamide in Fischer 344 rats. Toxicol. Appl. Pharmacol. 208 (2005) 199-209
11. Doerge D.R., da Costa G.G., McDaniel L.P., Churchwell M.I., Twaddle N.C., and Beland F.A. DNA adducts derived from administration of acrylamide and glycidamide to mice and rats. Mutat. Res. 580 (2005) 131-141
12. Dybing E., Farmer P.B., Andersen M., Fennell T.R., Lalljie S.P., Muller D.J., Olin S., Petersen B.J., Schlatter J., Scholz G., Scimeca J.A., Slimani N., Tornqvist M., Tuijtelaars S., and Verger P. Human exposure and internal dose assessments of acrylamide in food. Food Chem. Toxicol. 43 (2005) 365-410
13. Fennell T.R., Sumner S.C., Snyder R.W., Burgess J., Spicer R., Bridson W.E., and Friedman M.A. Metabolism and hemoglobin adduct formation of acrylamide in humans. Toxicol. Sci. 85 (2005) 447-459
14. Fleischauer A.T., and Arab L. Garlic and cancer: a critical review of the epidemiologic literature. J. Nutr. 131 (2001) 1032S-1040S
15. Friedman M. Chemistry, biochemistry, and safety of acrylamide: a review. J. Agric. Food Chem. 51 (2003) 4504-4526
16. Friedman M.A., Dulak L.H., and Stedham M.A. A lifetime oncogenicity study in rats with acrylamide. Fundam. Appl. Toxicol. 27 (1995) 95-105
17. Gamboa da Costa G., Churchwell M.I., Hamilton L.P., Von Tungeln L.S., Beland F.A., Marques M.M., and Doerge D.R. DNA adduct formation from acrylamide via conversion to glycidamide in adult and neonatal mice. Chem. Res. Toxicol. 16 (2003) 1328-1337
18. Gebhardt R., Hengstler J.G., Muller D., Glockner R., Buenning P., Laube B., Schmelzer E., Ullrich M., Utesch D., Hewitt N., Ringel M., Hilz B.R., Bader A., Langsch A., Koose T., Burger H.J., Maas J., and Oesch F. New hepatocyte in vitro systems for drug metabolism: metabolic capacity and recommendations for application in basic research and drug development, standard operation procedures. Drug Metab. Rev. 35 (2003) 145-213
19. Ghanayem B.I., McDaniel L.P., Churchwell M.I., Twaddle N.C., Snyder R., Fennell T.R., and Doerge D.R. Role of CYP2E1 in the epoxidation of acrylamide to glycidamide and formation of DNA and hemoglobin adducts. Toxicol. Sci. 88 (2005) 311-318
20. Ghanayem B.I., Witt K.L., Kissling G.E., Tice R.R., and Recio L. Absence of acrylamide-induced genotoxicity in CYP2E1-null mice: Evidence consistent with a glycidamide-mediated effect. Mutat. Res. 578 (2005) 284-297
21. Guyonnet D., Belloir C., Suschetet M., Siess M.H., and Le Bon A.M. Liver subcellular fractions from rats treated by organosulfur compounds from Allium modulate mutagen activation. Mutat. Res. 466 (2000) 17-26
22. IARC Monographs, 1993. Acrylamide, International Agency for Research on Cancer, Lyon.
23. Johnson K.A., Gorzinski S.J., Bodner K.M., Campbell R.A., Wolf C.H., Friedman M.A., and Mast R.W. Chronic toxicity and oncogenicity study on acrylamide incorporated in the drinking water of Fischer 344 rats. Toxicol. Appl. Pharmacol. 85 (1986) 154-168
24. Kwak M.K., Kim S.G., Kwak J.Y., Novak R.F., and Kim N.D. Inhibition of cytochrome P4502E1 expression by organosulfur compounds allylsulfide, allylmercaptan and allylmethylsulfide in rats. Biochem. Pharmacol. 47 (1994) 531-539
25. Loizou G.D., and Cocker J. The effects of alcohol and diallyl sulphide on CYP2E1 activity in humans: a phenotyping study using chlorzoxazone. Hum. Exp. Toxicol. 20 (2001) 321-327
26. Lupp A., Danz M., and Muller D. Morphology and cytochrome P450 isoforms expression in precision-cut rat liver slices. Toxicology 161 (2001) 53-66
27. Manjanatha, M.G., Aidoo, A., Shelton, S.D., Bishop, M.E., McDaniel, L.P., Lyn-Cook, L.E., Doerge, D.R., 2005. Genotoxicity of acrylamide and its metabolite glycidamide administered in drinking water to male and female Big Blue mice. Environ. Mol. Mutagen. June 14, [Epub ahead of print].
28. Milner J.A. Garlic: its anticarcinogenic and antitumorigenic properties. Nutr. Rev. 54 (1996) S82-S86
29. Milner J.A. Mechanisms by which garlic and allyl sulfur compounds suppress carcinogen bioactivation. Garlic and carcinogenesis. Adv. Exp. Med. Biol. 492 (2001) 69-81
30. Mottram D.S., Wedzicha B.L., and Dodson A.T. Acrylamide is formed in the Maillard reaction. Nature 419 (2002) 448-449
31. Mucci L.A., Dickman P.W., Steineck G., Adami H.O., and Augustsson K. Dietary acrylamide and cancer of the large bowel, kidney, and bladder: absence of an association in a population-based study in Sweden. Br. J. Cancer 88 (2003) 84-89
32. Paulsson B., Kotova N., Grawe J., Henderson A., Granath F., Golding B., and Tornqvist M. Induction of micronuclei in mouse and rat by glycidamide, genotoxic metabolite of acrylamide. Mutat. Res. 535 (2003) 15-24
33. Payne G.B., and Williams P.H. Reactions of hydrogen peroxide. VI. Alkaline epoxidation of acrylonitrile. J. Org. Chem. 26 (1961) 651-659
34. Pelucchi C., Galeone C., Levi F., Negri E., Franceschi S., Talamini R., Bosetti C., Giacosa A., and La Vecchia C. Dietary acrylamide and human cancer. Int. J. Cancer 118 (2006) 467-471
35. Segerback D., Calleman C.J., Schroeder J.L., Costa L.G., and Faustman E.M. Formation of N-7-(2-carbamoyl-2-hydroxyethyl)guanine in DNA of the mouse and the rat following intraperitoneal administration of [14C]acrylamide. Carcinogenesis 16 (1995) 1161-1165
36. Sorgel F., Weissenbacher R., Kinzig-Schippers M., Hofmann A., Illauer M., Skott A., and Landersdorfer C. Acrylamide: increased concentrations in homemade food and first evidence of its variable absorption from food, variable metabolism and placental and breast milk transfer in humans. Chemotherapy 48 (2002) 267-274
37. Sumner S.C., Fennell T.R., Moore T.A., Chanas B., Gonzalez F., and Ghanayem B.I. Role of cytochrome P450 2E1 in the metabolism of acrylamide and acrylonitrile in mice. Chem. Res. Toxicol. 12 (1999) 1110-1116
38. Tareke E., Rydberg P., Karlsson P., Eriksson S., and Tornqvist M. Analysis of acrylamide, a carcinogen formed in heated foodstuffs. J. Agric. Food Chem. 50 (2002) 4998-5006
39. Taubert D., Harlfinger S., Henkes L., Berkels R., and Schomig E. Influence of processing parameters on acrylamide formation during frying of potatoes. J. Agric. Food Chem. 52 (2004) 2735-2739
40. Twaddle N.C., McDaniel L.P., Gamboa da Costa G., Churchwell M.I., Beland F.A., and Doerge D.R. Determination of acrylamide and glycidamide serum toxicokinetics in B6C3F1 mice using LC-ES/MS/MS. Cancer Lett. 207 (2004) 9-17
41. US Environmental Protection Agency, 1985. Assessment of Health Risks from Exposure to Acrylamide. Washington, DC: Office on Toxic Substances.
42. Voigt M., and Wolf E. Knoblauch. HPLC von Knoblauchwirkstoffen in Extrakten, Pulver und Fertigarzneimitteln. Dtsch Apoth Ztg 126 (1986) 591-593
43. World Health Organization, 1985. Acrylamide. Environmental Health Criteria 49, Geneva.
44. Yang C.S., Chhabra S.K., Hong J.Y., and Smith T.J. Mechanisms of inhibition of chemical toxicity and carcinogenesis by diallyl sulfide (DAS) and related compounds from garlic. J. Nutr. 131 (2001) 1041S-1045S
45. Yoo J.S., Ishizaki H., and Yang C.S. Roles of cytochrome P450IIE1 in the dealkylation and denitrosation of N-nitrosodimethylamine and N-nitrosodiethylamine in rat liver microsomes. Carcinogenesis 11 (1990) 2239-2243