In Vitro Pro-Glycative Effects of Resveratrol and Caffeic Acid

Kurin, E.; Mučaji, P.; Nagy, M.

doi:10.2478/afpuc-2019-0004

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.

References

[1] Ahmed N. Advanced glycation endproducts—role in pathology of diabetic complications. Diabetes Res Clin Pract. 2005;67:3–21.10.1016/j.diabres.2004.09.004
Search in Google Scholar Back to article
[2] Alarcón De La Lastra C, Villegas I. Resveratrol as an antioxidant and pro-oxidant agent: Mechanisms and clinical implications. Biochem Soc Trans. 2007; 35:1156–1160.10.1042/BST0351156
Search in Google Scholar Back to article
[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;12:1496–1547.10.3390/12071496
Search in Google Scholar Back to article
[4] Asgary S, Naderi G, Sarrafzadegan N, et al. Anti-oxidant effect of flavonoids on hemoglobin glycosylation. Pharm Acta Helv. 1999;73:223–226.10.1016/S0031-6865(98)00025-9
Search in Google Scholar Back to article
[5] Baur JA, Sinclair DA. Therapeutic potential of resveratrol: The in vivo evidence. Nat Rev Drug Discovery. 2006;5:493–506.10.1038/nrd2060
Search in Google Scholar Back to article
[6] Benjakul S, Lertittikul W, Bauer F. Antioxidant activity of Maillard reaction products from a porcine plasma protein–sugar model system. Food Chem. 2005;93:189–196.10.1016/j.foodchem.2004.10.019
Search in Google Scholar Back to article
[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;218:249–255.10.1016/j.taap.2006.11.022
Search in Google Scholar Back to article
[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;37:69–78.10.1016/S0023-6438(03)00136-1
Search in Google Scholar Back to article
[9] Dufour C, Dangles O. Flavonoid–serum albumin complexation: determination of binding constants and binding sites by fluorescence spectroscopy. Biochim Biophys Acta. 2005;1721:164–173.10.1016/j.bbagen.2004.10.01315652191
Search in Google Scholar Back to article
[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;15:12889–12899.10.1002/chem.20090162719847825
Search in Google Scholar Back to article
[11] Fatima S, Jairajpuri DS, Saleemuddin M. A procedure for the rapid screening of Maillard reaction inhibitors. J Biochem Biophys. 2008;70:958–965.10.1016/j.jprot.2007.10.00218096239
Search in Google Scholar Back to article
[12] Gülçin I. Antioxidant activity of caffeic acid (3,4-dihydroxycinnamic acid). Toxicology. 2006;217:213–220.10.1016/j.tox.2005.09.01116243424
Search in Google Scholar Back to article
[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;27:979–988.10.1007/s11095-010-0055-420119749
Search in Google Scholar Back to article
[14] Halliwell B. Are polyphenols antioxidants or pro-oxidants? What do we learn from cell culture and in vivo studies? Arch Biochem Biophys. 2008;476:107–112.10.1016/j.abb.2008.01.02818284912
Search in Google Scholar Back to article
[15] Hanhineva K, Törrönen R, Bondia-Pons I, et al. Impact of dietary polyphenols on carbohydrate metabolism. Int J Mol Sci. 2010;11:1365–1402.10.3390/ijms11041365287112120480025
Search in Google Scholar Back to article
[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;78:772–778.10.1055/s-0031-129844022499559
Search in Google Scholar Back to article
[17] Kurin E, Mučaji P, Nagy M. In vitro antioxidant activities of three red wine polyphenols and their mixtures: an interaction. Molecules. 2012b;17:14336–14348.10.3390/molecules171214336626859023208468
Search in Google Scholar Back to article
[18] Kurin E, Fakhrudin N, Nagy M. eNOS Promoter Activation by Red Wine Polyphenols: an Interaction Study
Search in Google Scholar Back to article
[19] Acta Fac Pharm Univ Comen. 2013;60:27–33.10.11118/actaun201260070027
Search in Google Scholar Back to article
[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;100:669–677.10.1016/j.foodchem.2005.09.085
Search in Google Scholar Back to article
[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;94:75–80.10.1016/j.foodchem.2004.10.052
Search in Google Scholar Back to article
[22] Lunceford N, Gugliucci A. Ilex paraguariensis extracts inhibit AGE formation more efficiently than green tea. Fitoterapia. 2005;76:419–427.10.1016/j.fitote.2005.03.021
Search in Google Scholar Back to article
[23] Matus MH, Domínguez Z, Salas-Reyes M, Hernández J, Cruz-Sánchez S. Conformational study of caffeic acid derivatives. J Mol Struct. Theochem. 2010;953:175–181.10.1016/j.theochem.2010.05.028
Search in Google Scholar Back to article
[24] Miura T, Muraoka S, Ikeda N, Watanabe M, Fujimoto Y. Antioxidative and prooxidative action of stilbene derivatives. Basic Clin Pharmacol Toxicol. 2000;86:203–208.10.1034/j.1600-0773.2000.d01-36.x
Search in Google Scholar Back to article
[25] Morales FJ, Jiménez-Pérez S. Free radical scavenging capacity of Maillard reaction products as related to colour and fluorescence. Food Chem. 2001;72:119–125.10.1016/S0308-8146(00)00239-9
Search in Google Scholar Back to article
[26] Morimitsu Y, Yoshida K, Esaki S, Hirota A, Protein glycation inhibitors from thyme (Thymus vulgaris). Biosci Biotechnol. 1995;59:2018–2021.10.1271/bbb.59.2018
Search in Google Scholar Back to article
[27] Nicoli MC, Anese M, Parpinel M. Influence of processing on the antioxidant properties of fruit and vegetables. Trends Food Sci Tech. 1999;10:94–100.10.1016/S0924-2244(99)00023-0
Search in Google Scholar Back to article
[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;11:1679–1703.10.3390/ijms11041679287113320480037
Search in Google Scholar Back to article
[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.
Search in Google Scholar Back to article
[30] Simić A, Manojlović D, Šegan D, Todorović M. Electrochemical behavior and antioxidant and prooxidant activity of natural phenolics. Molecules. 2007;12:2327–2340.10.3390/12102327614916517978760
Search in Google Scholar Back to article
[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;46:139–146.10.1007/s00394-007-0644-017356796
Search in Google Scholar Back to article
[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;47:3974–3977.10.1021/jf990382w10552752
Search in Google Scholar Back to article
[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;113:78–84.10.1016/j.foodchem.2008.07.025
Search in Google Scholar Back to article
[34] Xia EQ, Deng GF, Guo YJ, Li HB. Biological activities of polyphenols from grapes. Int J Mol Sci. 2010;11: 622–646.10.3390/ijms11020622
Search in Google Scholar Back to article
[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;405:186–190.10.1016/S0014-5793(97)00185-3
Search in Google Scholar Back to article

In Vitro Pro-Glycative Effects of Resveratrol and Caffeic Acid

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