In Vitro Pro-Glycative Effects of Resveratrol and Caffeic Acid

E. Kurin 1 , P. Mučaji 1 , and M. Nagy 1
  • 1 Department of Pharmacognosy and Botany, Faculty of Pharmacy, Comenius University in Bratislava, Bratislava

Abstract

Resveratrol and caffeic acid belong to plant polyphenols and are known for their antioxidant effects. The aim of our research was to study their impact on Maillard reaction. This one occurs when the reducing saccharides react with amino groups of biomolecules including proteins, alter their protein conformation and transform to the variety of advanced glycation end products (AGEs). AGEs exhibit browning and generate fluorescence. There exist expectations that this oxidative protein glycosylation could be prevented by antioxidants. In this study, we incubated bovine serum albumin (BSA) with glucose for 7 days at 37°C and measured characteristic fluorescence and UV absorbance of the formed AGEs. Surprisingly, resveratrol and caffeic acid enhanced transformation of BSA to glycation products, which was confirmed either when cupric Cu(II) or ferric Fe(III) ions in nanomolar concentration were added to the system as pro-oxidant agent.

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  • [1] Ahmed N. Advanced glycation endproducts—role in pathology of diabetic complications. Diabetes Res Clin Pract. 2005;67:3–21.

  • [2] Alarcón De La Lastra C, Villegas I. Resveratrol as an antioxidant and pro-oxidant agent: Mechanisms and clinical implications. Biochem Soc Trans. 2007; 35:1156–1160.

  • [3] Apak R, Güçlü K, Demirata B, et al. Comparative evaluation of various total antioxidant capacity assays applied to phenolic compounds with the CUPRAC assay. Molecules. 2007;12:1496–1547.

  • [4] Asgary S, Naderi G, Sarrafzadegan N, et al. Anti-oxidant effect of flavonoids on hemoglobin glycosylation. Pharm Acta Helv. 1999;73:223–226.

  • [5] Baur JA, Sinclair DA. Therapeutic potential of resveratrol: The in vivo evidence. Nat Rev Drug Discovery. 2006;5:493–506.

  • [6] Benjakul S, Lertittikul W, Bauer F. Antioxidant activity of Maillard reaction products from a porcine plasma protein–sugar model system. Food Chem. 2005;93:189–196.

  • [7] Bhat SH, Azmi AS, Hadi SM. Prooxidant DNA breakage induced by caffeic acid in human peripheral lymphocytes: Involvement of endogenous copper and a putative mechanism for anticancer properties. Toxicol Appl Pharmacol. 2007;218:249–255.

  • [8] Billaud C, Maraschin C, Nicolas J. Inhibition of polyphenoloxidase from apple by Maillard reaction products prepared from glucose or fructose with l-cysteine under various conditions of pH and temperature. Lebensm Wiss u Technol. 2004;37:69–78.

  • [9] Dufour C, Dangles O. Flavonoid–serum albumin complexation: determination of binding constants and binding sites by fluorescence spectroscopy. Biochim Biophys Acta. 2005;1721:164–173.

  • [10] Fan GJ, Jin XL, Qian YP, et al. Hydroxycinnamic acids as DNA-cleaving agents in the presence of Cu II ions: Mechanism, structure-activity relationship, and biological implications. Chem Eur J. 2009;15:12889–12899.

  • [11] Fatima S, Jairajpuri DS, Saleemuddin M. A procedure for the rapid screening of Maillard reaction inhibitors. J Biochem Biophys. 2008;70:958–965.

  • [12] Gülçin I. Antioxidant activity of caffeic acid (3,4-dihydroxycinnamic acid). Toxicology. 2006;217:213–220.

  • [13] Hadi SM, Ullah MF, Azmi AS, et al. Resveratrol mobilizes endogenous copper in human peripheral lymphocytes leading to oxidative DNA breakage: A putative mechanism for chemoprevention of cancer. Pharm Res. 2010;27:979–988.

  • [14] Halliwell B. Are polyphenols antioxidants or pro-oxidants? What do we learn from cell culture and in vivo studies? Arch Biochem Biophys. 2008;476:107–112.

  • [15] Hanhineva K, Törrönen R, Bondia-Pons I, et al. Impact of dietary polyphenols on carbohydrate metabolism. Int J Mol Sci. 2010;11:1365–1402.

  • [16] Kurin E, Atanasov AG, Donath O, Heiss EH, Dirsch VM, Nagy M. Synergy study of the inhibitory potential of red wine polyphenols on vascular smooth muscle cellproliferation. 2012a;78:772–778.

  • [17] Kurin E, Mučaji P, Nagy M. In vitro antioxidant activities of three red wine polyphenols and their mixtures: an interaction. Molecules. 2012b;17:14336–14348.

  • [18] Kurin E, Fakhrudin N, Nagy M. eNOS Promoter Activation by Red Wine Polyphenols: an Interaction Study

  • [19] Acta Fac Pharm Univ Comen. 2013;60:27–33.

  • [20] Lertittikul W, Benjakul S, Tanaka M. Characteristics and antioxidative activity of Maillard reaction products from a porcine plasma protein–glucose model system as influenced by pH. Food Chem. 2007;100:669–677.

  • [21] López-Galilea I, Andueza S, Di Leonardo I, De Peña MP, Cid C. Influence of torrefacto roast on antioxidant and pro-oxidant activity of coffee. Food Chem. 2006;94:75–80.

  • [22] Lunceford N, Gugliucci A. Ilex paraguariensis extracts inhibit AGE formation more efficiently than green tea. Fitoterapia. 2005;76:419–427.

  • [23] Matus MH, Domínguez Z, Salas-Reyes M, Hernández J, Cruz-Sánchez S. Conformational study of caffeic acid derivatives. J Mol Struct. Theochem. 2010;953:175–181.

  • [24] Miura T, Muraoka S, Ikeda N, Watanabe M, Fujimoto Y. Antioxidative and prooxidative action of stilbene derivatives. Basic Clin Pharmacol Toxicol. 2000;86:203–208.

  • [25] Morales FJ, Jiménez-Pérez S. Free radical scavenging capacity of Maillard reaction products as related to colour and fluorescence. Food Chem. 2001;72:119–125.

  • [26] Morimitsu Y, Yoshida K, Esaki S, Hirota A, Protein glycation inhibitors from thyme (Thymus vulgaris). Biosci Biotechnol. 1995;59:2018–2021.

  • [27] Nicoli MC, Anese M, Parpinel M. Influence of processing on the antioxidant properties of fruit and vegetables. Trends Food Sci Tech. 1999;10:94–100.

  • [28] Pascual-Teresa S, Moreno DA, García-Viguera C. Flavanols and anthocyanins in cardiovascular health. A review of current evidence. Int J Mol Sci. 2010;11:1679–1703.

  • [29] Plaza M, Amigo-Benavent M, del Castillo MD, Ibáñez E, Herrero M. Neoformation of antioxidants in glycation model systems treated under subcritical water extraction conditions. Food Res. Int. 2010;43:1123–1129.

  • [30] Simić A, Manojlović D, Šegan D, Todorović M. Electrochemical behavior and antioxidant and prooxidant activity of natural phenolics. Molecules. 2007;12:2327–2340.

  • [31] Urios P, Grigorova-Borsos AM, Sternberg M. Flavonoids inhibit the formation of the cross-linking AGE pentosidine in collagen incubated with glucose, according to their structure. Eur J Nutr. 2007;46:139–146.

  • [32] Wang M, Jin Y, Ho CT. Evaluation of resveratrol derivatives as potential antioxidants and identification of a reaction product of resveratrol and 2,2-diphenyl-1-picryhydrazyl radical. J Agric Food Chem. 1999;47:3974–3977.

  • [33] Wu JW, Hsieh CL, Wang HY, Chen HY. Inhibitory effects of guava (Psidium guajava L.) leaf extracts and its active compounds on the glycation process of protein. Food Chem. 2009;113:78–84.

  • [34] Xia EQ, Deng GF, Guo YJ, Li HB. Biological activities of polyphenols from grapes. Int J Mol Sci. 2010;11: 622–646.

  • [35] Yamanaka N, Oda O, Nagao S. Prooxidant activity of caffeic acid, dietary non-flavonoid phenolic acid, on Cu2+-induced low density lipoprotein oxidation. FEBS Lett. 1997;405:186–190.

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