Investigation of the formation of (E)-2-butenal in oils and foods during frying

Food Research International

Volumn 62, Issue , 2014, Pages 43-49

  Papastergiadis, Antonios ^a   Fatouh, Amr ^b   Shrestha, Kshitij ^a   Van Langenhove, Herman ^a   De Meulenaer, Bruno ^a  

^a GHENT UNIVERSITY   (Belgium)

^b Ain Shams University   (Egypt)

Author keywords

(E) 2 butenal; Frying oils; Lipid oxidation; Stable isotope dilution assay

Indexed keywords

HEATING; ISOTOPES; OLIVE OIL; PALM OIL; PETROLEUM REFINING; UNSATURATED FATTY ACIDS;

BUTENAL; FATTY ACID COMPOSITION; FRYING OIL; INDOOR ENVIRONMENT; INTERNAL STANDARDS; LIPID OXIDATION; STABLE ISOTOPE DILUTION; STABLE ISOTOPE DILUTION ASSAY;

SUNFLOWER OIL;

EID: 84896272837     PISSN: 09639969     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodres.2014.02.046     Document Type: Article

References (39)

1. AOCS Official method for marine oil fatty acid composition by GLC. Official Methods and Recommended Practices of the American Oil Chemists Society 1989, AOCS Press, Champaign IL.
2. AOCS Additions and revisions, method Cd 18-90. Official Methods and Recommended Practices of the American Oil Chemists' Society 1992, AOCS Press, Champaign IL.
3. Cancilla D.A., Que Hee S.S. O-(2,3,4,5,6-pentafluorophenyl)methylhydroxylamine hydrochloride: A versatile reagent for the determination of carbonyl-containing compounds. Journal of Chromatography A 1992, 627:1-16.
4. Chung F.L., Hecht S.S. A study of chemical carcinogenesis.49. Formation of cyclic 1, N-2-adducts by reaction of deoxyguanosine with alpha-acetoxy-N-nitrosopyrrolidine, 4-(carbethoxynitrosamino)butanal, or crotonaldehyde. Cancer Research 1983, 43:1230-1235.
5. Chung F.L., Wu M.Y., Basudan A., Dyba M., Nath R.G. Regioselective formation of acrolein-derived cyclic 1, N-2-propanodeoxyguanosine adducts mediated by amino acids, proteins, and cell lysates. Chemical Research in Toxicology 2012, 25:1921-1928.
6. Chung F.L., Young R., Hecht S.S. A study of chemical carcinogenesis.61. Formation of cyclic 1, N2-propanodeoxyguanosine adducts in DNA upon reaction with acrolein or crotonaldehyde. Cancer Research 1984, 44:990-995.
7. Colombo G., Aldini G., Orioli M., Giustarini D., Gornati R., Rossi R., et al. Water-soluble alpha, beta-unsaturated aldehydes of cigarette smoke induce carbonylation of human serum albumin. Antioxidants & Redox Signaling 2010, 12:349-364.
8. EC European Commission Decision 2002/657/EC, implementing Council Directive 96/23/EC concerning the performance of analytical methods and the interpretation of results. Official Journal of the European Communities 2002, L221:8-36.
9. Eder E., Budiawan Cancer risk assessment for the environmental mutagen and carcinogen crotonaldehyde on the basis of TD50 and comparison with 1, N-2-propanodeoxyguanosine adduct levels. Cancer Epidemiology, Biomarkers & Prevention 2001, 10:883-888.
10. Esterbauer H. Lipid peroxidation and cancer. Free radicals 1982, 101-128. Academic Press, London. H. Esterbauer (Ed.).
11. Esterbauer H., Cheeseman K.H. Determination of aldehydic lipid-peroxidation products - Malonaldehyde and 4-hydroxynonenal. Methods in Enzymology 1990, 186:407-421.
12. Esterbauer H., Schaur R.J., Zollner H. Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Radical Biology and Medicine 1991, 11:81-128.
13. Ewert A., Granvogl M., Schieberle P. Development of two stable isotope dilution assays for the quantitation of acrolein in heat-processed fats. Journal of Agricultural and Food Chemistry 2011, 59:3582-3589.
14. Feron V.J., Til H.P., Devrijer F., Woutersen R.A., Cassee F.R., Vanbladeren P.J. Aldehydes - Occurrence, carcinogenic potential, mechanism of action and risk assessment. Mutation Research 1991, 259:363-385.
15. Frankel N.E. Lipid oxidation 2005, The Oily Press, Bridgwater, England.
16. Granvogl M., Schieberle P. Desirable (aroma-active) and undesirable (food-borne toxicants) bio-actives in foods: Formation and analysis. 246th ACS National Meeting & Exposition 2013.
17. Guillen M.D., Carton I., Salmeron J., Casas C. Headspace composition of cod liver oil and its evolution in storage after opening. First evidence of the presence of toxic aldehydes. Food Chemistry 2009, 114:1291-1300.
18. Guillen M.D., Goicoechea E. Formation of oxygenated alpha, beta-unsaturated aldehydes and other toxic compounds in sunflower oil oxidation at room temperature in closed receptacles. Food Chemistry 2008, 111:157-164.
19. Guillen M.D., Goicoechea E. Toxic oxygenated alpha, beta-unsaturated aldehydes and their study in foods: A review. Critical Reviews in Food Science and Nutrition 2008, 48:119-136.
20. Guillen M.D., Uriarte P.S. Aldehydes contained in edible oils of a very different nature after prolonged heating at frying temperature: Presence of toxic oxygenated alpha, beta unsaturated aldehydes. Food Chemistry 2012, 131:915-926.
21. IUPAC IUPAC standard methods for the analysis of oils, fats and derivatives 1987, Blackwell Scientific Publications. 7th ed.
22. LaFond S.I., Jerrell J.P., Cadwallader K.R., Artz W.E. Formation of 4-hydroxy-2-(E)-nonenal in a corn-soy oil blend: A controlled heating study using a French fried potato model. Journal of the American Oil Chemists Society 2011, 88:763-772.
23. Magnusson R., Nilsson C., Andersson B. Emissions of aldehydes and ketones from a two-stroke engine using ethanol and ethanol-blended gasoline as fuel. Environmental Science & Technology 2002, 36:1656-1664.
24. Mocak J., Bond A.M., Mitchell S., Scollary G. A statistical overview of standard (IUPAC and ACS) and new procedures for determining the limits of detection and quantification: Application to voltammetric and stripping techniques (technical report). Pure and Applied Chemistry 1997, 69:297-328.
25. Naveena B., Faustman C., Tatiyaborworntham N., Yin S., Ramanathan R., Mancini R. Detection of 4-hydroxy-2-nonenal adducts of turkey and chicken myoglobins using mass spectrometry. Food Chemistry 2010, 122:836-840.
26. Nawar W.W. Lipids. Food chemistry 1996, 226-314. Marcel Dekker, Inc. 3rd ed. O.R. Fennema (Ed.).
27. Papastergiadis A., Mubiru E., Van Langenhove H., De Meulenaer B. Development of a sensitive and accurate stable isotope dilution assay for the simultaneous determination of free 4-hydroxy-2-(E)-nonenal and 4-hydroxy-2-(E)-hexenal various food matrices by gas chromatography-mass spectrometry. Food Analytical Methods 2014, 7:836-843.
28. Poirier M., Fournier M., Brousseau P., Morin A. Effects of volatile aromatics, aldehydes, and phenols in tobacco smoke on viability and proliferation of mouse lymphocytes. Journal of toxicology and environmental health. Part A 2002, 65:1437-1451.
29. Rauniyar N., Prokai L. Detection and identification of 4-hydroxy-2-nonenal Schiff-base adducts along with products of Michael addition using data-dependent neutral loss-driven MS3 acquisition: Method evaluation through an in vitro study on cytochrome c oxidase modifications. Proteomics 2009, 9:5188-5193.
30. Saison D., De Schutter D.P., Delvaux F., Delvaux F.R. Determination of carbonyl compounds in beer by derivatisation and headspace solid-phase microextraction in combination with gas chromatography and mass spectrometry. Journal of Chromatography A 2009, 1216:5061-5068.
31. Seaman V.Y., Bennett D.H., Cahill T.M. Indoor acrolein emission and decay rates resulting from domestic cooking events. Atmospheric Environment 2009, 43:6199-6204.
32. Seppanen C.M., Csallany A.S. Formation of 4-hydroxynonenal, a toxic aldehyde, in soybean oil at frying temperature. Journal of the American Oil Chemists Society 2002, 79:1033-1038.
33. Shahidi F., Zhong Y. Lipid oxidation: Measurement methods. Bailey's industrial oil & fat products 2005, 357-385. John Wiley and Sons Inc. 6th ed. F. Shahidi (Ed.).
34. Shibamoto T. Analytical methods for trace levels of reactive carbonyl compounds formed in lipid peroxidation systems. Journal of Pharmaceutical and Biomedical Analysis 2006, 41:12-25.
35. StAngelo A.J. Lipid oxidation in foods. Critical Reviews in Food Science and Nutrition 1996, 36:175-224.
36. Uchida K. Histidine and lysine as targets of oxidative modification. Amino Acids 2003, 25:249-257.
37. Uchida K., Stadtman E.R. Modification of histidine-residues in proteins by reaction with 4-hydroxynonenal. Proceedings of the National Academy of Sciences of the United States of America 1992, 89:4544-4548.
38. Voulgaridou G.P., Anestopoulos I., Franco R., Panayiotidis M.I., Pappa A. DNA damage induced by endogenous aldehydes: Current state of knowledge. Mutation Research, Fundamental and Molecular Mechanisms of Mutagenesis 2011, 711:13-27.
39. Zervas E., Montagne X., Lahaye J. Emission of alcohols and carbonyl compounds from a spark ignition engine. Influence of fuel and air/fuel equivalence ratio. Environmental Science & Technology 2002, 36:2414-2421.