Analysis of sugar degradation products with α-dicarbonyl structure in carbonated soft drinks by UHPLC-DAD-MS/MS

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 43, 2013, Pages 10238-10245

  Gensberger, Sabrina ^a   Glomb, Marcus A ^b   Pischetsrieder, Monika ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

dicarbonyl compounds ( DCs); carbonated soft drinks (CSD); high fructose corn syrup (HFCS); o phenylenediamine (OPD); sugar degradation products

Indexed keywords

CARBONATED SOFT DRINKS; DICARBONYL COMPOUNDS; HIGH FRUCTOSE CORN SYRUPS (HFCS); OPHENYLENEDIAMINE (OPD); SUGAR DEGRADATION PRODUCTS;

CARBONATION; DEGRADATION; FRUCTOSE; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; SUGAR (SUCROSE);

BEVERAGES;

DRUG DERIVATIVE; FRUCTOSE; GALACTOSE; GALACTOSONE; GLUCOSONE; GLYOXAL; KETOSE; SWEETENING AGENT;

CARBONATED BEVERAGE; CHEMISTRY; CONFERENCE PAPER; GLYCATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; TANDEM MASS SPECTROMETRY;

CARBONATED BEVERAGES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FRUCTOSE; GALACTOSE; GLYOXAL; KETOSES; MAILLARD REACTION; SWEETENING AGENTS; TANDEM MASS SPECTROMETRY;

EID: 84887094818     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf3048466     Document Type: Conference Paper

References (31)

1. Economic Research Services (ERS) of U.S. Department of Agriculture (USDA). Food availabitily (per capita) data system; http://www.ers.usda.gov/ data/foodconsumption (accessed Sept 16, 2011).
2. White, J. S. Straight talk about high-fructose corn syrup: what it is and what it ain't Am. J. Clin. Nutr. 2008, 88, 1716S-1721S
3. Gensberger, S.; Mittelmaier, S.; Glomb, M. A.; Pischetsrieder, M. Identification and quantification of six major α-dicarbonyl process contaminants in high-fructose corn syrup Anal. Bioanal. Chem. 2012, 403, 2923-2931
4. Lo, C.-Y.; Li, S.; Wang, Y.; Tan, D.; Pan, M.-H.; Sang, S.; Ho, C.-T. Reactive dicarbonyl compounds and 5-hydroxymethylfurfural in carbonated beverages containing high fructose corn syrup Food Chem. 2008, 107, 1099-1105
5. Thornalley, P. J.; Rabbani, N. Dicarbonyls in cola drinks sweetened with sucrose or high fructose corn syrup. In The Maillard Reaction: Interface between Aging, Nutrition and Metabolism; Thomas, M.; Forbes, J., Eds.; Royal Society of Chemistry: Cambridge, UK, 2010; pp 158-163.
6. Ahmed, N.; Dobler, D.; Dean, M.; Thornalley, P. J. Peptide mapping identifies hotspot site of modification in human serum albumin by methylglyoxal involved in ligand binding and esterase activity J. Biol. Chem. 2005, 280, 5724-5732
7. Niwa, T. 3-Deoxyglucosone: metabolism, analysis, biological activity, and clinical implication J. Chromatogr., B: Biomed. Sci. Appl. 1999, 731, 23-36
8. Frischmann, M.; Bidmon, C.; Angerer, J.; Pischetsrieder, M. Identification of DNA adducts of methylglyoxal Chem. Res. Toxicol. 2005, 18, 1586-1592
9. More, S. S.; Raza, A.; Vince, R. The butter flavorant, diacetyl, forms a covalent adduct with 2-deoxyguanosine, uncoils DNA, and leads to cell death J. Agric. Food Chem. 2012, 60, 3311-3317
10. Breyer, V.; Frischmann, M.; Bidmon, C.; Schemm, A.; Schiebel, K.; Pischetsrieder, M. Analysis and biological relevance of advanced glycation end-products of DNA in eukaryotic cells FEBS J. 2008, 275, 914-925
11. Shapiro, R.; Sodum, R. S.; Everett, D. W.; Kundu, S. K. Reactions of nucleosides with glyoxal and acrolein IARC Sci. Publ. 1986, 165-173
12. Tauer, A.; Knerr, T.; Niwa, T.; Schaub, T. P.; Lage, C.; Passlick-Deetjen, J.; Pischetsrieder, M. In vitro formation of N ε-(carboxymethyl)lysine and imidazolones under conditions similar to continuous ambulatory peritoneal dialysis Biochem. Biophys. Res. Commun. 2001, 280, 1408-1414
13. Mittelmaier, S.; Pischetsrieder, M. Multistep ultrahigh performance liquid chromatography/tandem mass spectrometry analysis for untargeted quantification of glycating activity and identification of most relevant glycation products Anal. Chem. 2011, 83, 9660-9668
14. Linden, T.; Cohen, A.; Deppisch, R.; Kjellstrand, P.; Wieslander, A. 3,4-Dideoxyglucosone-3-ene (3,4-DGE): a cytotoxic glucose degradation product in fluids for peritoneal dialysis Kidney Int. 2002, 62, 697-703
15. Leung, J. C.; Chan, L. Y.; Li, F. F.; Tang, S. C.; Chan, K. W.; Chan, T. M.; Lam, M. F.; Wieslander, A.; Lai, K. N. Glucose degradation products downregulate ZO-1 expression in human peritoneal mesothelial cells: the role of VEGF Nephrol. Dial. Transplant. 2005, 20, 1336-1349
16. Mittelmaier, S.; Niwa, T.; Pischetsrieder, M. Chemical and physiological relevance of glucose degradation products in peritoneal dialysis J. Ren. Nutr. 2012, 22, 181-185
17. Glomb, M. A.; Pfahler, C. Synthesis of 1-deoxy- d -erythro-hexo-2,3- diulose, a major hexose Maillard intermediate Carbohydr. Res. 2000, 329, 515-523
18. Mittelmaier, S.; Funfrocken, M.; Fenn, D.; Fichert, T.; Pischetsrieder, M. Identification and quantification of the glucose degradation product glucosone in peritoneal dialysis fluids by HPLC/DAD/MSMS J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. 2010, 878, 877-882
19. Mittelmaier, S.; Funfrocken, M.; Fenn, D.; Pischetsrieder, M. 3-Deoxygalactosone, a new glucose degradation product in peritoneal dialysis fluids: identification, quantification by HPLC/DAD/MSMS and its pathway of formation Anal. Bioanal. Chem. 2011, 399, 1689-1697
20. Bruggemann, L.; Quapp, W.; Wennrich, R. Test for non-linearity concerning linear calibrated chemical measurements Accredit. Qual. Assur. 2006, 11, 625-631
21. de Revel, G.; Pripis-Nicolau, L.; Barbe, J.-C.; Bertrand, A. The detection of α-dicarbonyl compounds in wine by formation of quinoxaline derivatives J. Sci. Food Agric. 2000, 80, 102-108
22. Glomb, M. A.; Tschirnich, R. Detection of α-dicarbonyl compounds in Maillard reaction systems and in vivo J. Agric. Food Chem. 2001, 49, 5543-5550
23. Hollnagel, A.; Kroh, L. W. Formation of α-dicarbonyl fragments from mono- and disaccharides under caramelization and Maillard reaction conditions Z. Lebensm. Unters. Forsch. A 1998, 207, 50-54
24. Mittelmaier, S.; Funfrocken, M.; Fenn, D.; Berlich, R.; Pischetsrieder, M. Quantification of the six major α-dicarbonyl contaminants in peritoneal dialysis fluids by UHPLC/DAD/MSMS Anal. Bioanal. Chem. 2011, 401, 1183-1193
25. Marceau, E.; Yaylayan, V. A. Profiling of α-dicarbonyl content of commercial honeys from different botanical origins: identification of 3,4-dideoxyglucoson-3-ene (3,4-DGE) and related compounds J. Agric. Food Chem. 2009, 57, 10837-10844
26. Bravo, A.; Herrera, J. C.; Scherer, E.; Ju-Nam, Y.; Rubsam, H.; Madrid, J.; Zufall, C.; Rangel-Aldao, R. Formation of α-dicarbonyl compounds in beer during storage of Pilsner J. Agric. Food Chem. 2008, 56, 4134-4144
27. Daglia, M.; Papetti, A.; Aceti, C.; Sordelli, B.; Spini, V.; Gazzani, G. Isolation and determination of α-dicarbonyl compounds by RP-HPLC-DAD in green and roasted coffee J. Agric. Food Chem. 2007, 55, 8877-8882
28. Hellwig, M.; Degen, J.; Henle, T. 3-Deoxygalactosone, a "new" 1,2-dicarbonyl compound in milk products J. Agric. Food Chem. 2010, 58, 10752-10760
29. Degen, J.; Hellwig, M.; Henle, T. 1,2-Dicarbonyl compounds in commonly consumed foods J. Agric. Food Chem. 2012, 60, 7071-7079
30. Witowski, J.; Korybalska, K.; Wisniewska, J.; Breborowicz, A.; Gahl, G. M.; Frei, U.; Passlick-Deetjen, J.; Jorres, A. Effect of glucose degradation products on human peritoneal mesothelial cell function J. Am. Soc. Nephrol. 2000, 11, 729-739
31. Zimmeck, T.; Tauer, A.; Fuenfrocken, M.; Pischestrieder, M. How to reduce 3-deoxyglucosone and acetaldehyde in peritoneal dialysis fluids Perit. Dial. Int. 2002, 22, 350-356