Formation of α-dicarbonyl compounds in cookies made from wheat, hull-less barley and colored corn and its relation with phenolic compounds, free amino acids and sugars

European Food Research and Technology

Volumn 242, Issue 1, 2016, Pages 51-60

  Kocadağlı, Tolgahan ^a   Žilić, Slađana ^b   Taş, Neslihan Göncüoğlu ^a   Vančetović, Jelena ^b   Dodig, Dejan ^b   Gökmen, Vural ^a  

^a HACETTEPE UNIVERSITY   (Turkey)

^b Maize Research Institute   (Serbia)

Author keywords

Cereal cookies; Free amino acids; Phenolic compounds; Sucrose degradation; Dicarbonyl compounds

Indexed keywords

AMINO ACIDS; PHENOLS; SUGAR (SUCROSE);

CEREAL COOKIES; DICARBONYL COMPOUNDS; FREE AMINO ACIDS; PHENOLIC COMPOUNDS; SUCROSE DEGRADATION;

FLAVOR COMPOUNDS;

EID: 84953354159     PISSN: 14382377     EISSN: 14382385     Source Type: Journal    
DOI: 10.1007/s00217-015-2517-8     Document Type: Article

References (50)

1. Rabbani N, Thornalley PJ (2015) Dicarbonyl stress in cell and tissue dysfunction contributing to ageing and disease. Biochem Biophys Res Commun 458(2):221–226
2. Rabbani N, Thornalley PJ (2014) Dicarbonyl proteome and genome damage in metabolic and vascular disease. Biochem Soc Trans 42(2):425–432
3. Cerny C (2008) The aroma side of the Maillard reaction. Ann Ny Acad Sci 1126:66–71
4. Yaylayan VA (2003) Recent advances in the chemistry of Strecker degradation and Amadori rearrangement: Implications to aroma and color formation. Food Sci Technol Res 9(1):1–6
5. Weenen H (1998) Reactive intermediates and carbohydrate fragmentation in Maillard chemistry. Food Chem 62(4):393–401
6. Kroh LW (1994) Caramelisation in food and beverages. Food Chem 51(4):373–379
7. Yaylayan VA, Huyghues-Despointes A (1994) Chemistry of Amadori rearrangement products: analysis, synthesis, kinetics, reactions, and spectroscopic properties. Crit Rev Food Sci Nutr 34(4):321–369
8. Jiang Y, Hengel M, Pan C, Seiber JN, Shibamoto T (2013) Determination of toxic alpha-dicarbonyl compounds, glyoxal, methylglyoxal, and diacetyl, released to the headspace of lipid commodities upon heat treatment. J Agric Food Chem 61(5):1067–1071
9. Thornalley PJ, Langborg A, Minhas HS (1999) Formation of glyoxal, methylglyoxal and 3-deoxyglucosone in the glycation of proteins by glucose. Biochem J 344:109–116
10. Gobert J, Glomb MA (2009) Degradation of glucose: reinvestigation of reactive alpha-dicarbonyl compounds. J Agric Food Chem 57(18):8591–8597
11. Shibamoto T (2014) Diacetyl: occurrence, analysis, and toxicity. J Agric Food Chem 62(18):4048–4053
12. Smuda M, Glomb MA (2013) Fragmentation pathways during Maillard-induced carbohydrate degradation. J Agric Food Chem 61(43):10198–10208
13. Fujioka K, Shibamoto T (2004) Formation of genotoxic dicarbonyl compounds in dietary oils upon oxidation. Lipids 39(5):481–486
14. Usui T, Yanagisawa S, Ohguchi M, Yoshino M, Kawabata R, Kishimoto J, Arai Y, Aida K, Watanabe H, Hayase F (2007) Identification and determination of alpha-dicarbonyl compounds formed in the degradation of sugars. Biosci Biotech Bioch 71(10):2465–2472
15. Degen J, Hellwig M, Henle T (2012) 1,2-Dicarbonyl compounds in commonly consumed foods. J Agric Food Chem 60(28):7071–7079
16. Gensberger S, Mittelmaier S, Glomb MA, Pischetsrieder M (2012) Identification and quantification of six major alpha-dicarbonyl process contaminants in high-fructose corn syrup. Anal Bioanal Chem 403(10):2923–2931
17. Marceau E, Yaylayan VA (2009) Profiling of alpha-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 57(22):10837–10844
18. Weigel KU, Opitz T, Henle T (2004) Studies on the occurrence and formation of 1,2-dicarbonyls in honey. Eur Food Res Technol 218(2):147–151
19. Arribas-Lorenzo G, Morales FJ (2010) Analysis, distribution, and dietary exposure of glyoxal and methylglyoxal in cookies and their relationship with other heat-induced contaminants. J Agric Food Chem 58(5):2966–2972
20. Totlani VM, Peterson DG (2005) Reactivity of epicatechin in aqueous glycine and glucose Maillard reaction models: Quenching of C(2), C(3), and C(4) sugar fragments. J Agric Food Chem 53(10):4130–4135
21. Totlani VM, Peterson DG (2006) Epicatechin carbonyl-trapping reactions in aqueous Maillard systems: identification and structural elucidation. J Agric Food Chem 54(19):7311–7318
22. Lo CY, Li SM, Tan D, Pan MH, Sang SM, Ho CT (2006) Trapping reactions of reactive carbonyl species with tea polyphenols in simulated physiological conditions. Mol Nutr Food Res 50(12):1118–1128
23. Tan D, Wang Y, Lo CY, Sang SM, Ho CT (2008) Methylglyoxal: its presence in beverages and potential scavengers. Ann N Y Acad Sci 1126:72–75
24. Hu TY, Liu CL, Chyau CC, Hu ML (2012) Trapping of methylglyoxal by curcumin in cell-free systems and in human umbilical vein endothelial cells. J Agric Food Chem 60(33):8190–8196
25. Kokkinidou S, Peterson DG (2013) Response surface methodology as optimization strategy for reduction of reactive carbonyl species in foods by means of phenolic chemistry. Food Funct 4(7):1093–1104
26. Lv L, Shao X, Chen H, Ho CT, Sang S (2011) Genistein inhibits advanced glycation end product formation by trapping methylglyoxal. Chem Res Toxicol 24(4):579–586
27. Shao X, Bai N, He K, Ho CT, Yang CS, Sang S (2008) Apple polyphenols, phloretin and phloridzin: new trapping agents of reactive dicarbonyl species. Chem Res Toxicol 21(10):2042–2050
28. Lo CY, Hsiao WT, Chen XY (2011) Efficiency of trapping methylglyoxal by phenols and phenolic acids. J Food Sci 76(3):H90–H96
29. Mesias M, Navarro M, Gökmen V, Morales FJ (2013) Antiglycative effect of fruit and vegetable seed extracts: inhibition of AGE formation and carbonyl-trapping abilities. J Sci Food Agr 93(8):2037–2044
30. Totlani VM, Peterson DG (2007) Influence of epicatechin reactions on the mechanisms of Maillard product formation in low moisture model systems. J Agric Food Chem 55(2):414–420
31. Moskowitz MR, Bin Q, Elias RJ, Peterson DG (2012) Influence of endogenous ferulic acid in whole wheat flour on bread crust aroma. J Agric Food Chem 60(45):11245–11252
32. Troise AD, Fiore A, Colantuono A, Kokkinidou S, Peterson DG, Fogliano V (2014) Effect of olive mill wastewater phenol compounds on reactive carbonyl species and Maillard reaction end-products in ultrahigh-temperature-treated milk. J Agric Food Chem 62(41):10092–10100
33. Kokkinidou S, Peterson DG (2014) Control of Maillard-type off-flavor development in ultrahigh-temperature-processed bovine milk by phenolic chemistry. J Agric Food Chem 62(32):8023–8033
34. Kroh LW, Fiedler T, Wagner J (2008) alpha-Dicarbonyl compounds-key intermediates for the formation of carbohydrate-based melanoidins. Ann NY Acad Sci 1126:210–215
35. Žilić S, Hadži-Tašković Šukalović V, Dodig D, Maksimović V, Maksimović M, Basić Z (2011) Antioxidant activity of small grain cereals caused by phenolics and lipid soluble antioxidants. J Cereal Sci 54(3):417–424
36. Žilić S, Serpen A, Akıllıoğlu G, Gökmen V, Vancetovic J (2012) Phenolic compounds, carotenoids, anthocyanins, and antioxidant capacity of colored maize (Zea mays L.) kernels. J Agric Food Chem 60(5):1224–1231
37. Žilić S, Dodig D, Milašinović Šeremešić M, Kandić V, Konstadinović M, Prodanović S, Savić Đ (2011) Small grain cereals compared for dietary fibre and protein contents. Genetika 43(2):381–395
38. AACC (2000) Approved methods of the American Association of Cereal Chemists, 10th edn. Association of Cereal Chemists, St Paul
39. Antoine C, Peyron S, Lullien-Pellerin V, Abecassis J, Rouau X (2004) Wheat bran tissue fractionation using biochemical markers. J Cereal Sci 39(3):387–393
40. Singleton VL, Orthofer R, Lamuela-Raventos RM (1999) Analysis of total phenols and other oxidation substrates and antioxidants by means of Folin-Ciocalteu reagent. Oxid Antioxid A 299:152–178
41. Kocadağlı T, Özdemir KS, Gökmen V (2013) Effects of infusion conditions and decaffeination on free amino acid profiles of green and black tea. Food Res Int 53(2):720–725
42. Kocadağlı T, Gökmen V (2014) Investigation of alpha-dicarbonyl compounds in baby foods by high-performance liquid chromatography coupled with electrospray ionization mass spectrometry. J Agric Food Chem 62:7714–7720
43. Abdel-Aal ESM (2011) In: Awika JM, Piironen V, Bean S (eds) Anthocyanin-pigmented grain products. American Chemical Society, Washington
44. Van der Fels-Klerx HJ, Capuano E, Nguyen HT, Mogol BA, Kocadağlı T, Taş NG, Hamzalıoğlu A, Van Boekel MAJS, Gökmen V (2014) Acrylamide and 5-hydroxymethylfurfural formation during baking of biscuits: NaCl and temperature-time profile effects and kinetics. Food Res Int 57:210–217
45. Gensberger S, Glomb MA, Pischetsrieder M (2013) Analysis of sugar degradation products with alpha-dicarbonyl structure in carbonated soft drinks by UHPLC-DAD-MS/MS. J Agric Food Chem 61(43):10238–10245
46. Vander Jagt DL, Hunsaker LA (2003) Methylglyoxal metabolism and diabetic complications: roles of aldose reductase, glyoxalase-1, betaine aldehyde dehydrogenase and 2-oxoaldehyde dehydrogenase. Chem Biol Interact 143:341–351
47. Degen J, Vogel M, Richter D, Hellwig M, Henle T (2013) Metabolic transit of dietary methylglyoxal. J Agric Food Chem 61:10253–10260
48. Kato H, van Chuyen N, Shinoda T, Sekiya F, Hayase F (1990) Metabolism of 3-deoxyglucosone, an intermediate compound in the Maillard reaction, administered orally or intravenously to rats. Biochim Biophys Acta 1035:71–76
49. Collard F, Vertommen D, Fortpied J, Duester G, Van Schaftingen E (2007) Identification of 3-deoxyglucosone dehydrogenase as aldehyde dehydrogenase 1A1 (retinaldehyde dehydrogenase 1). Biochimie 89:369–373
50. Degen J, Beyer H, Heymann B, Hellwig M, Henle T (2014) Dietary influence on urinary excretion of 3-deoxyglucosone and its metabolite 3-deoxyfructose. J Agric Food Chem 62:2449–2456