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Mitigation of ovalbumin glycation in vitro by its treatment with green tea polyphenols

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Abstract

Polyphenols are known as inhibitors of glycation since they alter the pathways of the Maillard reaction by several mechanisms involving antioxidant activity, reactive dicarbonyl trapping, inhibition of sugar autoxidation, and amino group binding. Green tea is a rich source of polyphenols. This study aimed to investigate the effects of protein modification with green tea polyphenols on glycation potential of ovalbumin. For this purpose, green tea infusion was prepared and ovalbumin was treated with that infusion at alkaline pH conditions in order to let oxidation of polyphenols to quinone forms and formation of covalent linkages between quinones and amine residues of protein. This modified ovalbumin was heated with glucose at 90 °C. Furosine, the compound formed from N-ε-fructoselysine during acid hydrolysis, and N-ε-carboxymethyl lysine (CML) as indicators of early and advanced glycation, respectively, were monitored. Free lysine concentrations and antioxidant activity were measured in order to enlighten the interaction mechanism. Results showed that treatment of ovalbumin with green tea phenolics before reaction with glucose has a potential to limit glycation. In total 15 % less furosine was formed in treated ovalbumin than control ovalbumin upon heating at 90 °C for 1 h, whereas 14 % less CML was formed.

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References

  1. Wu Q, Li S, Li X, Fu X, Sui Y, Guo T, Xie B, Sun Z (2014) A significant inhibitory effect on advanced glycation end product formation by catechin as the major metabolite of lotus seedpod oligomeric procyanidins. Nutrients 6:3230–3244

    Article  Google Scholar 

  2. Kanska U, Boratynski J (2002) Thermal glycation of proteins by d-glucose and D-fructose. Arch Immunol Ther Exp (Warsz) 50:61–66

    CAS  Google Scholar 

  3. Hayase F, Shibuya T, Sato J, Yamamoto M (1996) Effects of oxygen and transition metals on the advanced Maillard reaction of proteins with glucose. Biosci Biotechnol Biochem 60:1820–1825

    Article  CAS  Google Scholar 

  4. Miller AG, Hegge S, Uhlmann A, Gerrard JA (2005) A continuous enzyme assay and characterisation of fructosyl amine oxidase enzymes (EC 1.5.3). Arch Biochem Biophys 434:60–66

    Article  CAS  Google Scholar 

  5. Yim HS, Kang SO, Hah YC, Chock PB, Yim MB (1995) Free radicals generated during the glycation reaction of amino acids by methylglyoxal. A model study of protein-cross-linked free radicals. J Biol Chem 270:28228–28233

    Article  CAS  Google Scholar 

  6. Ames JM (2007) Dietary Maillard reaction products: implications for human health and disease. Czech J Food Sci 27:66–69

    Google Scholar 

  7. Baynes JW (2001) The role of AGEs in aging: causation or correlation. Exp Gerontol 36:1527–1537

    Article  CAS  Google Scholar 

  8. Vlassara H (2005) Advanced glycation in health and disease role of the modern environment. Ann N Y Acad Sci 1043:452–460

    Article  CAS  Google Scholar 

  9. Chompoo J, Upadhyay A, Kishimoto W, Makise T, Tawata S (2011) Advanced glycation end products inhibitors from Alpinia zerumbet rhizomes. Food Chem 129:709–715

    Article  CAS  Google Scholar 

  10. Peng X, Cheng KW, Ma J, Chen B, Ho CT, Lo C, Chen F, Wang M (2008) Cinnamon bark proanthocyanidins as reactive carbonyl scavengers to prevent the formation of advanced glycation endproducts. J Agric Food Chem 56:1907–1911

    Article  CAS  Google Scholar 

  11. Sun Z, Peng X, Liu J, Fan KW, Wang M, Chen F (2010) Inhibitory effects of microalgal extracts on the formation of advanced glycation endproducts (AGEs). Food Chem 120:261–267

    Article  CAS  Google Scholar 

  12. Wang X, Zhang LS, Dong LL (2012) Inhibitory effect of polysaccharides from pumpkin on advanced glycation end-products formation and aldose reductase activity. Food Chem 130:821–825

    Article  CAS  Google Scholar 

  13. Boušová I, Martin J, Jahodář L, Dušek J, Palička V, Dršata J (2005) Evaluation of in vitro effects of natural substances of plant origin using a model of protein glycoxidation. J Pharm Biomed Anal 37:957–962

    Article  Google Scholar 

  14. Mesías M, Navarro M, Martínez-Saez N, Ullate M, del Castillo MD, Morales FJ (2014) Antiglycative and carbonyl trapping properties of the water soluble fraction of coffee silverskin. Food Res Int 62:1120–1126

    Article  Google Scholar 

  15. Delgado-Andrade C (2016) Carboxymethyl-lysine: thirty years of investigation in the field of AGE formation. Food Funct 7:46–57

    Article  CAS  Google Scholar 

  16. Noda Y, Peterson DG (2007) Structure-reactivity relationships of flavan-3-ols on product generation in aqueous glucose/glycine model systems. J Agric Food Chem 55:3686–3691

    Article  CAS  Google Scholar 

  17. Totlani VM, Peterson DG (2005) Reactivity of epicatechin in aqueous glycine and glucose Maillard reaction models: quenching of C2, C3, and C4 sugar fragments. J Agric Food Chem 53:4130–4135

    Article  CAS  Google Scholar 

  18. 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 55:414–420

    Article  CAS  Google Scholar 

  19. Bin Q, Peterson DG, Elias RJ (2012) Influence of phenolic compounds on the mechanisms of pyrazinium radical generation in the Maillard reaction. J Agric Food Chem 60:5482–5490

    Article  CAS  Google Scholar 

  20. Babu PV, Sabitha KE, Shyamaladevi CS (2008) Effect of green tea extract on advanced glycation and cross-linking of tail tendon collagen in streptozotocin induced diabetic rats. Food Chem Toxicol 46:280–285

    Article  CAS  Google Scholar 

  21. Doğan E, Gökmen V (2015) Mechanism of the interaction between insoluble wheat bran and polyphenols leading to increased antioxidant capacity. Food Res Int 69:189–193

    Article  Google Scholar 

  22. Gökmen V, Serpen A, Morales FJ (2009) Determination of furosine in thermally processed foods by hydrophilic interaction liquid chromatography. J AOAC Int 92:1460–1463

    Google Scholar 

  23. Palermo M, Fiore A, Fogliano V (2012) Okara promoted acrylamide and carboxymethyl-lysine formation in bakery products. J Agric Food Chem 60:10141–10146

    Article  CAS  Google Scholar 

  24. Akıllıoğlu HG, Gökmen V (2014) Effects of hydrophobic and ionic interactions on glycation of casein during Maillard reaction. J Agric Food Chem 62:11289–11295

    Article  Google Scholar 

  25. Kocadaglı T, Zilic S, Tas NG, Vancetovic J, Dodig D, Gökmen V (2016) 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. Eur Food Res Technol 242:51–60

    Article  Google Scholar 

  26. Serpen A, Gökmen V, Fogliano V (2012) Total antioxidant capacities of raw and cooked meats. Meat Sci 90:60–65

    Article  CAS  Google Scholar 

  27. Celik EE, Gökmen V, Fogliano V (2013) Soluble antioxidant compounds regenerate the antioxidants bound to insoluble parts of foods. J Agric Food Chem 61:10329–10334

    Article  CAS  Google Scholar 

  28. Zilic S, Akıllıoğlu G, Serpen A, Barac M, Gökmen V (2012) Effects of isolation, enzymatic hydrolysis, heating, hydratation and Maillard reaction on the antioxidant capacity of cereal and legume proteins. Food Res Int 49:1–6

    Article  CAS  Google Scholar 

  29. Medina-Navarro R, Durán-Reyes G, Díaz-Flores M, Vilar-Rojas C (2010) Protein antioxidant response to the stress and the relationship between molecular structure and antioxidant function. PLoS ONE 5:1–11

    Article  Google Scholar 

  30. Çelik EE, Gökmen V (2014) Investigation of the interaction between soluble antioxidants in green tea and insoluble dietary fiber bound antioxidants. Food Res Int 63C:266–270

    Article  Google Scholar 

  31. Wang H, Provan GJ, Helliwell K (2000) Tea flavonoids: their functions, utilisation and analysis. Trend Food Sci Technol 11:152–160

    Article  CAS  Google Scholar 

  32. Colahan-Sederstrom PM, Peterson DG (2005) Inhibition of key aroma compound generated during ultrahigh-temperature processing of bovine milk via epicatechin addition. J Agric Food Chem 53:398–402

    Article  CAS  Google Scholar 

  33. Guerra PV, Yaylayan VA (2014) Interaction of flavanols with amino acids: postoxidative reactivity of the B-ring of catechin with glycine. J Agric Food Chem 62:3831–3836

    Article  CAS  Google Scholar 

  34. Sang S, Shao X, Bai N, Lo CY, Yang CS, Ho CT (2007) Tea polyphenol (−)-epigallocatechin-3-gallate: a new trapping agent of reactive dicarbonyl species. Chem Res Toxicol 20:1862–1870

    Article  CAS  Google Scholar 

  35. Yin J, Hedegaard RV, Skibsted LH, Andersen ML (2014) Epicatechin and epigallocatechin gallate inhibit formation of intermediary radicals during heating of lysine and glucose. Food Chem 146:48–55

    Article  CAS  Google Scholar 

  36. Zhang X, Chen F, Wang M (2014) Antioxidant and antiglycation activity of selected dietary polyphenols in a cookie model. J Agric Food Chem 62:1643–1648

    Article  CAS  Google Scholar 

  37. Rawel HM, Kroll J, Rohn S (2001) Reactions of phenolic substances with lysozyme-physicochemical characterisation and proteolytic digestion of the derivatives. Food Chem 72:59–71

    Article  CAS  Google Scholar 

  38. Silván JM, Assar SH, Chou S, del Castillo MD, Ames JM (2011) Control of the Maillard reaction by ferulic acid. Food Chem 128:208–213

    Article  Google Scholar 

  39. Silvan JM, Chou S, Ames JM, del Castillo MD (2014) Glycation is regulated by isoflavones. Food & Funct 5:2036–2042

    Article  CAS  Google Scholar 

  40. Fujiwara Y, Kiyota N, Tsurushima K, Yoshitomi M, Mera K, Sakashita N, Takeya M, Ikeda T, Araki T, Nohara T, Nagai R (2011) Natural compounds containing a catechol group enhance the formation of N ε-(carboxymethyl) lysine of the Maillard reaction. Free Radic Biol Med 50:883–891

    Article  CAS  Google Scholar 

  41. Nagai R, Shirakawa J, Ohno R, Moroishi N, Nagai M (2014) Inhibition of AGEs formation by natural products. Amino Acids 46:261–266

    Article  CAS  Google Scholar 

  42. Fernandez-Gomez B, Ullate M, Picariello G, Ferranti P, Mesa MD, del Castillo MD (2015) New knowledge on the antiglycoxidative mechanism of chlorogenic acid. Food Funct 6:2081–2090

    Article  CAS  Google Scholar 

  43. Koschinsky T, He CJ, Mitsuhashi T, Bucala R, Liu C, Buenting C, Heitmann K, Vlassara H (1997) Orally absorbed reactive glycation products (glycotoxins): an environmental risk factor in diabetic nephropathy. Proc Natl Acad Sci 94:6474–6479

    Article  CAS  Google Scholar 

  44. Uribarri J, Cai W, Peppa M, Goodman S, Ferrucci L, Striker G, Vlassara H (2007) Circulating glycotoxins and dietary advanced glycation endproducts: two links to inflammatory response, oxidative stress, and aging. J Gerontol A Biol Sci Med Sci 62:427–433

    Article  Google Scholar 

  45. Vlassara H, Cai W, Crandall J, Goldberg T, Oberstein R, Dardaine V, Peppa M, Rayfield EJ (2002) Inflammatory mediators are induced by dietary glycotoxins, a major risk factor for diabetic angiopathy. Proc Natl Acad Sci 99:15596–15601

    Article  CAS  Google Scholar 

  46. Uribarri J, Peppa M, Cai W, Goldberg T, Lu M, He C, Vlassara H (2003) Restriction of dietary glycotoxins reduces excessive advanced glycation end products in renal failure patients. J Am Soc Nephrol 14:728–731

    Article  CAS  Google Scholar 

  47. Uribarri J, Peppa M, Cai W, Goldberg T, Lu M, Baliga S, Vassalotti JA, Vlassara H (2003) Dietary glycotoxins correlate with circulating advanced glycation end product levels in renal failure patients. Am J Kidney Dis 42:532–538

    Article  CAS  Google Scholar 

  48. Vlassara H, Cai W, Goodman S, Pyzik R, Yong A, Chen X, Zhu L, Neade T, Beeri M, Silverman JM, Ferrucci L, Tansman L, Striker GE, Uribarri J (2009) Protection against loss of innate defenses in adulthood by low advanced glycation end products (AGE) intake: role of the antiinflammatory AGE receptor-1. J Clin Endocrinol Metab 94:4483–4491

    Article  CAS  Google Scholar 

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Correspondence to Vural Gökmen.

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Cömert, E.D., Akıllıoğlu, H.G. & Gökmen, V. Mitigation of ovalbumin glycation in vitro by its treatment with green tea polyphenols. Eur Food Res Technol 243, 11–19 (2017). https://doi.org/10.1007/s00217-016-2717-x

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  • DOI: https://doi.org/10.1007/s00217-016-2717-x

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