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

SCOPE Acrolein (AC) and acrylamide (AA) are food contaminants generated by heat treatment. We studied human exposure after consumption of potato crisps by monitoring excretion of mercapturic acids (MAs) in urine. METHODS AND RESULTS MA excretion was monitored in human urine collected up to 72 h after ingestion of a test meal of experimental (study 1: 1 mg AA/150 g) or commercially available (study 2: 44 μg AA plus 4.6 μg AC/175 g) potato crisps. MA contents were analysed after purification via SPE using HPLC-ESI-MS/MS. On the basis of the area under the curve values of MAs excreted in urine, the total excretion of AC-related MAs exceeded that of AA-related MAs up to 12 times in study 1 and up to four times in study 2. Remarkably, AC content of potato crisps of study 2 was found to be only about 1/10 the AA content, as determined by isotope dilution headspace GC/MS. CONCLUSION Our results indicate substantially higher exposure to AC from potato crisps than to AA. Total AC in such foods may encompass bioavailable AC forms not detected by headspace GC/MS. Both findings may also apply to other heat processed foods.

[1]  S. Tannenbaum,et al.  N7-glycidamide-guanine DNA adduct formation by orally ingested acrylamide in rats: a dose-response study encompassing human diet-related exposure levels. , 2012, Chemical research in toxicology.

[2]  A. Lampen,et al.  Toxicology and risk assessment of acrolein in food. , 2011, Molecular nutrition & food research.

[3]  Z. de Lourdes Cardeal,et al.  Determination of acrolein in french fries by solid-phase microextraction gas chromatography and mass spectrometry. , 2011, Journal of chromatography. A.

[4]  P. Schieberle,et al.  Development of two stable isotope dilution assays for the quantitation of acrolein in heat-processed fats. , 2011, Journal of agricultural and food chemistry.

[5]  G. Eisenbrand,et al.  Biological effects of acrylamide after daily ingestion of various foods in comparison to water: a study in rats. , 2011, Molecular nutrition & food research.

[6]  J. Schwöbel,et al.  Prediction of michael-type acceptor reactivity toward glutathione. , 2010, Chemical research in toxicology.

[7]  S. Hecht,et al.  Detection of 7-(2'-carboxyethyl)guanine but not 7-carboxymethylguanine in human liver DNA. , 2010, Chemical research in toxicology.

[8]  C. Ramassamy,et al.  Potential role of acrolein in neurodegeneration and in Alzheimer's disease. , 2010, Current molecular pharmacology.

[9]  B. Blount,et al.  Simultaneous determination of six mercapturic acid metabolites of volatile organic compounds in human urine. , 2009, Chemical research in toxicology.

[10]  U. Fuhr,et al.  In vivo Role of Cytochrome P450 2E1 and Glutathione-S-Transferase Activity for Acrylamide Toxicokinetics in Humans , 2009, Cancer Epidemiology Biomarkers & Prevention.

[11]  T. Schettgen,et al.  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. , 2008, Rapid communications in mass spectrometry : RCM.

[12]  B. Lyn‐Cook,et al.  Acrylamide: a dietary carcinogen formed in vivo? , 2008, Journal of agricultural and food chemistry.

[13]  D. Hatsukami,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. , 2007, Chemical research in toxicology.

[14]  S. Hecht,et al.  Detection and quantitation of acrolein-derived 1,N2-propanodeoxyguanosine adducts in human lung by liquid chromatography-electrospray ionization-tandem mass spectrometry. , 2007, Chemical research in toxicology.

[15]  W Slob,et al.  Approaches to the risk assessment of genotoxic carcinogens in food: a critical appraisal. , 2006, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[16]  Lutz Edler,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 , 2006 .

[17]  G. Eisenbrand,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. , 2006, Molecular nutrition & food research.

[18]  U. Fuhr,et al.  Toxicokinetics of Acrylamide in Humans after Ingestion of a Defined Dose in a Test Meal to Improve Risk Assessment for Acrylamide Carcinogenicity , 2006, Cancer Epidemiology Biomarkers & Prevention.

[19]  J. Angerer,et al.  Excretion of mercapturic acids of acrylamide and glycidamide in human urine after single oral administration of deuterium-labelled acrylamide , 2006, Archives of Toxicology.

[20]  John F. Young,et al.  Toxicokinetics of acrylamide and glycidamide in Fischer 344 rats. , 2005, Toxicology and applied pharmacology.

[21]  J. Angerer,et al.  Determination of the major mercapturic acids of acrylamide and glycidamide in human urine by LC-ESI-MS/MS. , 2005, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[22]  H. van der Voet,et al.  Calculations of dietary exposure to acrylamide. , 2005, Mutation research.

[23]  D. Marko,et al.  DNA strand breaking capacity of acrylamide and glycidamide in mammalian cells. , 2005, Mutation research.

[24]  M. Díaz-Flores,et al.  Glucose-stimulated acrolein production from unsaturated fatty acids , 2004, Human & experimental toxicology.

[25]  R. Carchman,et al.  Chemical composition, cytotoxicity and mutagenicity of smoke from US commercial and reference cigarettes smoked under two sets of machine smoking conditions. , 2004, Toxicology.

[26]  M. Churchwell,et al.  DNA adduct formation from acrylamide via conversion to glycidamide in adult and neonatal mice. , 2003, Chemical research in toxicology.

[27]  D. Zyzak,et al.  Acrylamide formation mechanism in heated foods. , 2003, Journal of agricultural and food chemistry.

[28]  B. Lau,et al.  Acrylamide in foods: occurrence, sources, and modeling. , 2003, Journal of agricultural and food chemistry.

[29]  F. Johnson,et al.  Mutagenesis by acrolein-derived propanodeoxyguanosine adducts in human cells. , 2002, Biochemistry.

[30]  Shyam Biswal,et al.  Acrolein causes transcriptional induction of phase II genes by activation of Nrf2 in human lung type II epithelial (A549) cells. , 2002, Toxicology letters.

[31]  F. Chung,et al.  Formation of cyclic deoxyguanosine adducts from ω-3 and ω-6 polyunsaturated fatty acids under oxidative conditions , 2002 .

[32]  T. Perfetti,et al.  "IARC group 2A Carcinogens" reported in cigarette mainstream smoke. , 2000, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[33]  N. Sauvageot,et al.  Glycerol metabolism in Lactobacillus collinoides: production of 3-hydroxypropionaldehyde, a precursor of acrolein. , 2000, International journal of food microbiology.

[34]  F. Gonzalez,et al.  Role of cytochrome P450 2E1 in the metabolism of acrylamide and acrylonitrile in mice. , 1999, Chemical research in toxicology.

[35]  F. Chung,et al.  1,N2-propanodeoxyguanosine adducts: potential new biomarkers of smoking-induced DNA damage in human oral tissue. , 1998, Cancer research.

[36]  R. A. Parent,et al.  Metabolism and Distribution of [2,3‐14C]Acrolein in Sprague‐Dawley Rats , 1996, Journal of applied toxicology : JAT.

[37]  E. Faustman,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. , 1995, Carcinogenesis.

[38]  A. Hoberman,et al.  Reproductive study of acrolein on two generations of rats , 1992 .

[39]  R. Smith,et al.  Acrolein initiates rat urinary bladder carcinogenesis. , 1992, Cancer research.

[40]  V. Feron,et al.  Aldehydes: occurrence, carcinogenic potential, mechanism of action and risk assessment. , 1991, Mutation research.

[41]  P. Boor,et al.  3‐Hydroxypropylmercapturic acid: A biologic marker of exposure to allylic and related compounds , 1989, Journal of applied toxicology : JAT.

[42]  S. Hecht,et al.  Formation of cyclic 1,N2-propanodeoxyguanosine adducts in DNA upon reaction with acrolein or crotonaldehyde. , 1984, Cancer research.

[43]  D. Henschler,et al.  Mutagenic properties of allylic and alpha, beta-unsaturated compounds: consideration of alkylating mechanisms. , 1982, Xenobiotica; the fate of foreign compounds in biological systems.

[44]  E. Eder,et al.  Structure-mutagenicity relationship in α,β-unsaturated carbonylic compounds and their corresponding allylic alcohols , 1982 .

[45]  J. F. Stevens,et al.  Acrolein: sources, metabolism, and biomolecular interactions relevant to human health and disease. , 2008, Molecular nutrition & food research.

[46]  G. Eisenbrand,et al.  Acrylamide and glycidamide: approach towards risk assessment based on biomarker guided dosimetry of genotoxic/mutagenic effects in human blood. , 2005, Advances in experimental medicine and biology.

[47]  M J Peake,et al.  Reference range and method comparison studies for enzymatic and Jaffé creatinine assays in plasma and serum and early morning urine. , 2000, Clinical laboratory.