Phenolic compounds reduce formation of Nε-(carboxymethyl)lysine and pyrazines formed by Maillard reactions in a model bread system

Food Chemistry

Volumn 231, Issue , 2017, Pages 175-184

  Mildner Szkudlarz, Sylwia ^a   Siger, Aleksander ^a   Szwengiel, Artur ^a   Przygoński, Krzysztof ^b   Wojtowicz, Elżbieta ^b   Zawirska Wojtasiak, Renata ^a  

^a POZNA UNIVERSITY OF LIFE SCIENCES   (Poland)

^b State Research Institute   (Poland)

Author keywords

Available lysine losses; Bread; N (carboxymethyl)lysine (CML); Phenolic compounds; Pyrazines

Indexed keywords

AMINO ACIDS; FLAVONOIDS; FOOD PRODUCTS; ORGANIC COMPOUNDS;

AVAILABLE LYSINES; BREAD; CARBOXYMETHYL; PHENOLIC COMPOUNDS; PYRAZINES;

PHENOLS;

CATECHIN; FERULIC ACID; LYSINE; N EPSILON (CARBOXYMETHYL)LYSINE; PHENOL DERIVATIVE; PYRAZINE DERIVATIVE; UNCLASSIFIED DRUG; N(6)-(1-CARBOXYETHYL)LYSINE;

ANTIOXIDANT ACTIVITY; ARTICLE; BREAD; CHEMICAL STRUCTURE; CLUSTER ANALYSIS; CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; GLYCATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEOPHILICITY; PROTEIN DETERMINATION; SIGNAL NOISE RATIO; THERMOSTABILITY; ANALOGS AND DERIVATIVES;

BREAD; CATECHIN; LYSINE; MAILLARD REACTION; PHENOLS; PYRAZINES;

EID: 85016414053     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2017.03.126     Document Type: Article

References (39)

1. AOAC, Official methods of analysis. 16th ed., 1995, AOAC International, Arlington, VA.
2. Blandino, M., Sovrani, V., Marinaccio, F., Reyneri, A., Rolle, L., Giacosa, S., Arlorio, M., Nutritional and technological quality of bread enriched with an intermediated pearled wheat fraction. Food Chemistry 141:3 (2013), 2549–2557.
3. Bors, W., Heller, W., Michel, C., Saran, M., Flavonoids as antioxidants: Determination of radical-scavenging efficiencies. Methods in Enzymology 186 (1990), 343–355.
4. Chinchansure, A.A., Korwar, A.M., Kulkarni, M.J., Joshi, S.P., Recent development of plant products with anti-glycation activity: A review. RSC Advances 5:39 (2015), 31113–31138.
5. Drusch, S., Faist, V., Erbersdobler, H., Determination of N∊-carboxymethyllysine in milk products by a modified reversed-phase HPLC method. Food Chemistry 65:4 (1999), 547–553.
6. Favreau-Farhadi, N., Pecukonis, L., Barrett, A., The inhibition of Maillard browning by different concentrations of rosmarinic acid and epigallocatechin-3-gallate in model, bakery, and fruit systems. Journal of Food Science, 80(10), 2015 C2140-6.
7. Fujiwara, Y., Kiyota, N., Tsurushima, K., Yoshitomi, M., Mera, K., Sakashita, N., Nagai, R., Natural compounds containing a catechol group enhance the formation of Nε-(carboxymethyl)lysine of the Maillard reaction. Free Radical Biology and Medicine 50:7 (2011), 883–891.
8. Granato, D., Katayama, F.C.U., de Castro, I.A., Phenolic composition of South American red wines classified according to their antioxidant activity, retail price and sensory quality. Food Chemistry 129:2 (2011), 366–373.
9. He, J., Zeng, M., Zheng, Z., He, Z., Chen, J., Simultaneous determination of N ε-(carboxymethyl) lysine and N ε-(carboxyethyl) lysine in cereal foods by LC–MS/MS. European Food Research and Technology 238:3 (2013), 367–374.
10. Hull, G.L.J., Woodside, J.V., Ames, J.M., Cuskelly, G.J., Nε-(carboxymethyl)lysine content of foods commonly consumed in a Western style diet. Food Chemistry 131:1 (2012), 170–174.
11. Kim, J., Kim, K.M., Kim, C.-S., Sohn, E., Lee, Y.M., Jo, K., Kim, J.S., Puerarin inhibits the retinal pericyte apoptosis induced by advanced glycation end products in vitro and in vivo by inhibiting NADPH oxidase-related oxidative stress. Free Radical Biology & Medicine 53:2 (2012), 357–365.
12. Kocadağlı, T., Žilić, S., Taş, N.G., Vančetović, J., Dodig, D., Gökmen, V., 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 242:1 (2015), 51–60.
13. Leyva-Corral, J., Quintero-Ramos, A., Camacho-Dávila, A., de Jesús Zazueta-Morales, J., Aguilar-Palazuelos, E., Ruiz-Gutiérrez, M.G., de Jesús Ruiz-Anchondo, T., Polyphenolic compound stability and antioxidant capacity of apple pomace in an extruded cereal. LWT – Food Science and Technology 65 (2016), 228–236.
14. Mesías, M., Navarro, M., Gökmen, V., Morales, F.J., Antiglycative effect of fruit and vegetable seed extracts: Inhibition of AGE formation and carbonyl-trapping abilities. Journal of the Science of Food and Agriculture 93:8 (2013), 2037–2044.
15. Mildner-Szkudlarz, S., Siger, A., Szwengiel, A., Bajerska, J., Natural compounds from grape by-products enhance nutritive value and reduce formation of CML in model muffins. Food Chemistry 172 (2015), 78–85.
16. Navarro, M., Morales, F.J., In vitro investigation on the antiglycative and carbonyl trapping activities of hydroxytyrosol. European Food Research and Technology 242:7 (2016), 1101–1110.
17. Nerlich, A.G., Schleicher, E.D., Nɛ-(carboxymethyl)lysine in atherosclerotic vascular lesions as a marker for local oxidative stress. Atherosclerosis (Shannon, Ireland) 144 (1999), 41–47.
18. Pacyński, M., Zawirska-Wojtasiak, R., Mildner-Szkudlarz, S., Improving the aroma of gluten-free bread. LWT – Food Science and Technology 63:1 (2015), 706–713.
19. Paraskevopoulou, A., Chrysanthou, A., Koutidou, M., Characterisation of volatile compounds of lupin protein isolate-enriched wheat flour bread. Food Research International 48:2 (2012), 568–577.
20. Peng, X., Cheng, K.W., Ma, J., Chen, B., Ho, C.T., Lo, C., Wang, M., Cinnamon bark proanthocyanidins as reactive carbonyl scavengers to prevent the formation of advanced glycation endproducts. Journal of Agricultural and Food Chemistry 56:6 (2008), 1907–1911.
21. Peng, X., Ma, J., Cheng, K.-W., Jiang, Y., Chen, F., Wang, M., The effects of grape seed extract fortification on the antioxidant activity and quality attributes of bread. Food Chemistry 119:1 (2010), 49–53.
22. Ramı́rez-Jiménez, A., Garcı́a-Villanova, B., Guerra-Hernández, E., Effect of storage conditions and inclusion of milk on available lysine in infant cereals. Food Chemistry 85:2 (2004), 239–244.
23. Rawel, H.M., Czajka, D., Rohn, S., Kroll, J., Interactions of different phenolic acids and flavonoids with soy proteins. International Journal of Biological Macromolecules 30:3–4 (2002), 137–150.
24. Rawel, H.M., Kroll, J., Rohn, S., Reactions of phenolic substances with lysozyme — physicochemical characterisation and proteolytic digestion of the derivatives. Food Chemistry 72:1 (2001), 59–71.
25. Reddy, V.P., Beyaz, A., Inhibitors of the Maillard reaction and AGE breakers as therapeutics for multiple diseases. Drug Discovery Today 11:13–14 (2006), 646–654.
26. Rohn, S., Buchner, N., Driemel, G., Rauser, M., Kroh, L.W., Thermal degradation of onion quercetin glucosides under roasting conditions. Journal of Agricultural and Food Chemistry 55:4 (2007), 1568–1573.
27. Rupasinghe, H.P.V., Wang, L., Huber, G.M., Pitts, N.L., Effect of baking on dietary fibre and phenolics of muffins incorporated with apple skin powder. Food Chemistry 107:3 (2008), 1217–1224.
28. Shao, X., Bai, N., He, K., Ho, C.T., Yang, C.S., Sang, S., Apple polyphenols, phloretin and phloridzin: New trapping agents of reactive dicarbonyl species. Chemical Research in Toxicology 21:10 (2008), 2042–2050.
29. Singh, R., Barden, A., Mori, T., Beilin, L., Advanced glycation end-products: A review. Diabetologia 44:2 (2001), 129–146.
30. Thornalley, P.J., Use of aminoguanidine (Pimagedine) to prevent the formation of advanced glycation endproducts. Archives of Biochemistry and Biophysics 419:1 (2003), 31–40.
31. Totlani, V.M., Peterson, D.G., Influence of epicatechin reactions on the mechanisms of Maillard product formation in low moisture model systems. Journal of Agricultural and Food Chemistry 55:2 (2007), 414–420.
32. Turchetti, B., Pinelli, P., Buzzini, P., Romani, A., Heimler, D., Franconi, F., Martini, A., In vitro antimycotic activity of some plant extracts towards yeast and yeast-like strains. Phytotherapy Research: PTR 19:1 (2005), 44–49.
33. Wang, J., Sun, B., Cao, Y., Tian, Y., Protein glycation inhibitory activity of wheat bran feruloyl oligosaccharides. Food Chemistry 112:2 (2009), 350–353.
34. Wang, R., Zhou, W., Stability of tea catechins in the breadmaking process. Journal of Agricultural and Food Chemistry 52:26 (2004), 8224–8229.
35. Wang, Y., Effects of naturally occurring phenolic compounds on the formation of Maillard aroma. (Ph.D. dissertation), 2000, Rutgers State University.
36. Wu, J.-W., Hsieh, C.-L., Wang, H.-Y., Chen, H.-Y., Inhibitory effects of guava (Psidium guajava L.) leaf extracts and its active compounds on the glycation process of protein. Food Chemistry 113:1 (2009), 78–84.
37. Wu, Q., Li, S., Li, X., Fu, X., Sui, Y., Guo, T., Sun, Z., A significant inhibitory effect on advanced glycation end product formation by catechin as the major metabolite of lotus seedpod oligomeric procyanidins. Nutrients 6:8 (2014), 3230–3244.
38. Yu, A.-N., Zhang, A.-D., The effect of pH on the formation of aroma compounds produced by heating a model system containing L-ascorbic acid with L-threonine/L-serine. Food Chemistry 119:1 (2010), 214–219.
39. Zheng, L.W., Chung, H., Kim, Y.-S., Effects of dicarbonyl trapping agents, antioxidants, and reducing agents on the formation of furan and other volatile components in canned-coffee model systems. Food Research International 75 (2015), 328–336.