Analysis, distribution, and dietary exposure of glyoxal and methylglyoxal in cookies and their relationship with other heat-induced contaminants

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 5, 2010, Pages 2966-2972

  Arribas Lorenzo, Gema ^a   Morales, Francisco J ^a  

^a INSTITUTO DEL FRÍO CSIC   (Spain)

Author keywords

Acrylamide; Glyoxal; Hydroxymethylfurfural; Methylglyoxal Cookies

Indexed keywords

GLYOXAL; METHYLGLYOXAL;

ARTICLE; FOOD CONTAMINATION; HEAT;

FOOD CONTAMINATION; GLYOXAL; HOT TEMPERATURE; PYRUVALDEHYDE;

EID: 77949359498     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf902815p     Document Type: Article

References (37)

1. Thornalley, P. J. Dicarbonyl intermediates in the Maillard reaction. Ann. N.Y. Acad. Sci. 2005, 1043, 111-117.
2. Talukdar, D.; Chaudhuri, B. S.; Ray, M.; Ray, S. Critical evaluation of toxic versus beneficial effects of methylglyoxal. Biochemistry (Moscow), 2009, 74, 1059-1069.
3. Lapolla, A.; Flamini, R.; Lupo, A.; Arico, N. C.; Rugiu, C.; Reitano, R.; Tubaro, M.; Ragazzi, E.; Seraglia, R.; Traldi, P. Evaluation of glyoxal and methylglyoxal in uremic patients under peritoneal dialysis. Ann. N.Y. Acad. Sci. 2005, 1043, 217-224.
4. Thornalley, P. J. Glycation free adduet accumulation in renal disease: the new AGE. Pediatr. Nephrol. 2005, 20, 1515-1522.
5. Kalapos, M. P. Methylglyoxal in living organisms: chemistry, biochemistry, toxicology and biological implications. Toxicol. Lett. 1999, 110, 145-175.
6. Baskaran, S.; Balasubramanian, K. A. Toxicity of methylglyoxal towards rat enterocytes and coloncytes. Biochem. Int. 1990, 21, 165-174.
7. Ueno, H.; Nakamuro, K.; Sayato, Y.; Okada, S. DNA lesion in rat hepatocytes induces by in vitro and in vivo exposure to glyoxal. Mutat. Res. 1991, 260, 115-119.
8. Schnuch, A.; Uter, W.; Geier, J.; Frosch, P. J.; Rustemeyer, T. Contact allergies in healthcare workers. Results from the IVDK. Acta Derm. Venereol. 1998, 78, 358-363.
9. Uter, W.; Schwanitz, H. J.; Lessmann, H.; Schnuch, A. Glyoxal is an important allergen for (medical care) cleaning staff. Int. J. Hyg. Environ. Health 2001, 204, 251-253.
10. Nemet, I.; Varga-Defterdarovic, L.; Turk, Z. Methylglyoxal in food and living organisms. Mol. Nutr. Food Res. 2006, 50, 115-117.
11. Homoki-Farkas, P.; Örsi, F.; Kroh, L. W. Methylglyoxal determination from different carbohydrates during heat processing. Food Chem. 1991, 59, 157-163.
12. Niyati-Shirkhodaee, F.; Shibamoto, T. Gas-chromatographic analysis of glyoxal and methylglyoxal formed from lipids and relatedcompounds upon ultraviolet-irradiation. J. Agric. Food Chem. 1993, 41, 227-230.
13. Yamaguchi, M.; Ishida, J.; Xuan-Xuan, Z.; Nakamura, M.; Yoshitake, T. Determination of glyoxal, methylglyoxal, diacethyl, and 2,3-pentanedione in fermented foods by high-performance liquid chromatography with fluorescence detection. J. Liq. Chromatogr. 1994, 17, 203-211.
14. Weigel, K. U.; Opitz, T.; Henle, T. Studies on the occurrence and formation of 1,2-dicarbonyls in honey. Eur. Food Res. Technol. 2004, 218, 147-157.
15. De Revel, G.; Bertrand, A. A method for the detection of carbonyl compounds in wine: glyoxal and methylglyoxal. J. Sci. Food Agric 1993, 61, 267-272.
16. Barros, A.; Rodrigues, J. A.; Almeida, P. J.; Oliva-Teles, M. T. Determination of glyoxal, methylglyoxal and diacetyl in selected beer and wine by HPLC with UV spectrophotometric detection after derivatization with o-phenylendiamine. J. Liq. Chromatogr. Relat. Technol. 1999, 22, 2061-2069.
17. Hirayama, T.; Yamada, N.; Nohara, M.; Fukui, S. The existence of the 1, 2-diacrbonyl compounds glyoxal, methylglyoxal and diacetyl in autoxidised oils. J. Sci. Food Agric. 1984, 35, 1357-1362.
18. Nagao, M.; Fujita, Y.; Sugimura, T.; Kosuge, T. Methylglyoxal in beverages and foods: its mutagenicity and carcinogenicity. IARC Sci. Publ. 1986, 70, 283-291.
19. Thornalley, P. J.; Langborg, A.; Minhas, H. S. Formation of glyoxal, methylglyoxal and 3-deoxyglucosone in the glycation of proteins by glucose. Biochem. J. 1999, 344, 109-116.
20. De Revel, G.; Pripis-Nicolau, L.; Berbe, J. C.; Bertrand, A. The detection of α-dicarbonyl compounds in wine by formation of quinoxaline derivates. J. Sci. Food Agric. 2000, 50, 102-108.
21. Acrylamide; International Agency for Research on Cancer: Lyon, France, 1994.
22. Surh, Y.; Tannenbaun, S. Activation of the Maillard reaction product 5-(hydroxymethyl)furfural to strong mutagens via allylic sulfonation and chlorination. Chem. Res. Toxicol. 1994, 7, 313-318.
23. Amrein, T. M.; Andres, L.; Manzardo, G. G. G.; Amado, R. Investigations on the promoting effect of ammonium hydrogencarbonate on the formation of acrylamide in model system. J. Agric. Food Chem. 2006, 54, 10253-10261.
24. Arribas-Lorenzo, G.; Fogliano, V.; Morales, F. J. Acrylamide formation in a cookie system as influenced by the oil phenol profile and degree of oxidation. Eur. Food Res. Technol. 2009, 229, 63-72.
25. Rufián-Henares, J. A.; Delgado-Andrade, C.; Morales, F. J. Application of a fast HPLC method for simultaneously determination of furanic compounds and glucosylisomaltol in breakfast cereals. J. AOAC Int. 2006, 89, 161-165.
26. MARM. La Alimentación en España; Ministerio de Agricultura, Pesca y Alimentación: Madrid, Spain, 2009.
27. Dhar, A.; Desai, K.; Liu, J.; Wu, L. Methylglyoxal, protein binding and biological samples: are we getting the true measure? J. Chromatogr., B 2009, 577, 1093-1100.
28. Gildersleeve, D. L.; Tobes, M. C.; Natale, R. B. Rapid analysis for methylglyoxal bis(guanylhydrazone) by reversed-phase ion-pair liquid chromatography. Clin. Chem. 1985, 31, 1979-1984.
29. Daglia, M.; Papetti, A.; Aceti, C.; Sordelli, B.; Spini, V.; Gazzani, G. Isolation and determination of a-dicarbonyl compounds by RPHPLC-DAD in green and roasted coffee. J. Agric. Food Chem. 2007, 55, 8877-8882.
30. Roiter, I. M.; Borovikova, L. A. Level of volatile carbonyl compounds in bread during the addition of enzyme preparations. Khlebopek. Konditer. Promst. 1972, 14, 14-15.
31. Weenen, H. Reactive intermediates and carbohydrate fragmentation in Maillard chemistry. Food Chem. 1998, 62, 393-401.
32. Wells-Knecht, K. J.; Zyzak, D. V.; Litchfield, J. E.; Thorpe, S. R.; Baynes, J. W. Mechanism of autoxidative glycosylation: identification of glyoxal and arabinose as intermediates in the autoxidative modification of proteins by glucose. Biochemistry 1995, 34, 3702-3709.
33. Hayashi, T.; Namiki, M. Role of sugar fragmentation in an early stage browning of amino-carbonyl reaction of sugar with amino acid. Agric. Biol. Chem. 1986, 50, 1965-1970.
34. Mottram, D. S.; Wedzicha, B. L.; Dodson, A. T. Acrylamide is formed in the Maillard reaction. Nature 2002, 419, 449-450.
35. Stadler, R. H.; Blank, I.; Varga, N.; Robert, F.; Hau, J.; Guy, P. A.; Robert, M. C.; Riediker, S. Acrylamide from Maillard reaction products. Nature 2002, 419, 449-450.
36. Tareke, E.; Rydberg, P.; Karlsson, P.; Eriksson, S.; Tornqvist, M. Analysis of acrylamide, a carcinogen formed in heated foodstuffs. J. Agric. Food Chem. 2002, 50, 4998-5006.
37. Yuan, Y.; Zhao, G-h.; Hu, X-s.; Wu, J-h.; Liu, J.; Chen, F. High correlation of methylglyoxal with acrylamide formation in glucose/ asparagine Maillard reaction model. Eur. Food Res. Technol. 2008, 226, 1301-1307.