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Antioxidant activity of 3,4,5-trihydroxyphenylacetamide derivatives

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Abstract

A series of amide derivatives of 3,4,5-trihydroxyphenylacetic acid was synthesized in two steps. The antioxidant activities were evaluated by using four different in vitro models such as ABTS and DPPH radical scavenging activity and FTC and TBA anti-lipid peroxidation activity. Most of compounds were more powerful radical scavengers than vitamin C and were comparable to Trolox. It was found that there were no direct correlations between radical scavenging and anti-peroxidation activities. The inhibitory activity of compound on lipid peroxidation showed remarkable dependency on both the number of phenolic hydroxyl group and the length of methylene linker in N-arylalkyl group of amide. Compound 14, a conjugate of 3,4,5-trihydroxyphenylacetic acid and dopamine, was found as powerful antioxidant as propyl gallate in all four antioxidant assays.

Graphical Abstract

A series of amide derivatives of 3,4,5-trihydroxyphenylacetic acid was synthesized. The antioxidant activities were evaluated by using four different in vitro models such as ABTS and DPPH radical scavenging activity and FTC and TBA anti-lipid peroxidation activity. Compound 14, a conjugate of dopamine, was found as powerful antioxidant as propyl gallate in all four antioxidant assays.

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References

  • Belin, F., P. Barthélémy, K. Ruiz, J.M. Lacombe, and B. Pucci. 2003. Synthetic gallic acid derivatives as models for a comprehensive study of antioxidant activity. Helvetica Chimica Acta 86: 247–265.

    Article  CAS  Google Scholar 

  • Çetinkaya, Y., H. Göçer, A. Menzek, and İ. Gülçin. 2012. Synthesis and antioxidant properties of (3,4-Dihydroxyphenyl)(2,3,4-trihydroxyphenyl) methanone and its derivatives. Archiv der Pharmazie 345: 323–334.

    Article  PubMed  Google Scholar 

  • Chan, E., C.Y. Wong, C.W. Wan, C.Y. Kwok, J.H. Wu, K.M. Ng, C.H. So, A.L. Au, C.C. Poon, S.W. Seto, Y.W. Kwan, P.H. Yu, and S.W. Chan. 2010. Evaluation of anti-oxidant capacity of root of Scutellaria baicalensis georgi, in comparison with roots of polygonum multiflorum thunb and panax ginseng CA Meyer. American Journal of Chinese Medicine 38: 815–827.

    Article  PubMed  Google Scholar 

  • Du, J., C. Miao, X. Zhang, I.-H. Jeong, E.M. Son, S. You, B.-J. Lee, and D.-K. Kim. 2011. Antiproliferation of hela cells by 3,4,5-trihydroxy-N-[2-p-tolylethyl]-benzamide is associated with induction of DNA damage and inhibition of DNA replication. Toxicology in Vitro 25: 1535–1541.

    Article  CAS  PubMed  Google Scholar 

  • Erkan, N., G. Ayranci, and E. Ayranci. 2008. Antioxidant activities of rosemary (Rosmarinus officinalis L.) extract, blackseed (Nigella sativa L.) essential oil, carnosic acid, rosmarinic acid and sesamol. Food Chemistry 110: 76–82.

    Article  CAS  Google Scholar 

  • Fiuza, S.M., C. Gomes, L.J. Teixeira, M.T. Girão Da Cruz, M.N.D.S. Cordeiro, N. Milhazes, F. Borges, and M.P.M. Marques. 2004. Phenolic acid derivatives with potential anticancer properties—A structure–activity relationship study. Part 1: Methyl, propyl and octyl esters of caffeic and gallic acids. Bioorganic and Medicinal Chemistry 12: 3581–3589.

    Article  CAS  PubMed  Google Scholar 

  • Gülçin, İ. 2012. Antioxidant activity of food constituents: An overview. Archives of Toxicology 86: 345–391.

    Article  PubMed  Google Scholar 

  • Halliwell, B., and S. Chirico. 1993. Lipid peroxidation: Its mechanism, measurement, and significance. The American Journal of Clinical Nutrition 57: 715S–724S.

    CAS  PubMed  Google Scholar 

  • Huang, D., B. Ou, and R.L. Prior. 2005. The chemistry behind antioxidant capacity assays. Journal of Agriculture and Food Chemistry 53: 1841–1856.

    Article  CAS  Google Scholar 

  • Kikuzaki, H., and N. Nakatani. 1993. Antioxidant effects of some ginger constituents. Journal of Food Science 58: 1407–1410.

    Article  CAS  Google Scholar 

  • Lu, Z., G. Nie, P.S. Belton, H. Tang, and B. Zhao. 2006. Structure–activity relationship analysis of antioxidant ability and neuroprotective effect of gallic acid derivatives. Neurochemistry International 48: 263–274.

    Article  CAS  PubMed  Google Scholar 

  • Navarro-Perán, E., J. Cabezas-Herrera, L. Sánchez-Del-Campo, F. García-Cánovas, and J.N. Rodríguez-López. 2008. The anti-inflammatory and anti-cancer properties of epigallocatechin-3-gallate are mediated by folate cycle disruption, adenosine release and NF-κB suppression. Inflammation Research 57: 472–478.

    Article  PubMed  Google Scholar 

  • Niki, E., E. Komuro, M. Takahashi, S. Urano, E. Ito, and K. Terao. 1988. Oxidative hemolysis of erythrocytes and its inhibition by free radical scavengers. Journal of Biological Chemistry 263: 19809–19814.

    CAS  PubMed  Google Scholar 

  • Ottolenghi, A. 1959. Interaction of ascorbic acid and mitochondrial lipides. Archives of Biochemistry and Biophysics 79: 355–363.

    Article  CAS  Google Scholar 

  • Pal, C., S. Bindu, S. Dey, A. Alam, M. Goyal, M.S. Iqbal, S. Sarkar, R. Kumar, K.K. Halder, M.C. Debnath, S. Adhikari, and U. Bandyopadhyay. 2012. Tryptamine-gallic acid hybrid prevents non-steroidal anti-inflammatory drug-induced gastropathy. Journal of Biological Chemistry 287: 3495–3509.

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  • Pratt, D.A., K.A. Tallman, and N.A. Porter. 2011. Free radical oxidation of polyunsaturated lipids: New mechanistic insights and the development of peroxyl radical clocks. Accounts of Chemical Research 44: 458–467.

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  • Re, R., N. Pellegrini, A. Proteggente, A. Pannala, M. Yang, and C. Rice-Evans. 1999. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology and Medicine 26: 1231–1237.

    Article  CAS  PubMed  Google Scholar 

  • Sato, Y., S. Kamo, T. Takahashi, and Y. Suzuki. 1995. Mechanism of free radical-induced hemolysis of human erythrocytes: Hemolysis by water-soluble radical initiator. Biochemistry (Moscow) 34: 8940–8949.

    Article  CAS  Google Scholar 

  • Siquet, C., F. Paiva-Martins, J.L.F.C. Lima, S. Reis, and F. Borges. 2006. Antioxidant profile of dihydroxy- and trihydroxyphenolic acids-A structure–activity relationship study. Free Radical Research 40: 433–442.

    Article  CAS  PubMed  Google Scholar 

  • Valko, M., D. Leibfritz, J. Moncol, M.T.D. Cronin, M. Mazur, and J. Telser. 2007. Free radicals and antioxidants in normal physiological functions and human disease. The International Journal of Biochemistry and Cell Biology 39: 44–84.

    Article  CAS  PubMed  Google Scholar 

  • Vijayavel, K., R.D. Gomathi, K. Durgabhavani, and M.P. Balasubramanian. 2004. Sublethal effect of naphthalene on lipid peroxidation and antioxidant status in the edible marine crab Scylla serrata. Marine Pollution Bulletin 48: 429–433.

    Article  CAS  PubMed  Google Scholar 

  • Wu, J., H. Sugiyama, L.H. Zeng, D. Mickle, and W. T-W. 1998. Evidence of trolox and some gallates as synergistic protectors of erythrocytes against peroxyl radicals. Biochemistry and Cell Biology 76: 661–664.

    Article  CAS  PubMed  Google Scholar 

  • Yang, Y., R. Sharma, J.-Z. Cheng, M.K. Saini, N.H. Ansari, U.P. Andley, S. Awasthi, and Y.C. Awasthi. 2002. Protection of HLE B-3 cells against hydrogen peroxide- and naphthalene-induced lipid peroxidation and apoptosis by transfection with hGSTA1 and hGSTA2. Investigative Ophthalmology and Visual Science 43: 434–445.

    PubMed  Google Scholar 

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Acknowledgments

The research was supported by the Bisa Research Grant of Keimyung University in 2012.

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Correspondence to Jinho Lee.

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Kim, J., Hong, V.S. & Lee, J. Antioxidant activity of 3,4,5-trihydroxyphenylacetamide derivatives. Arch. Pharm. Res. 37, 324–331 (2014). https://doi.org/10.1007/s12272-013-0189-0

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