Effect of vanillin and its acid and alcohol derivatives on the diphenolase activity of mushroom tyrosinase

Document Type: Original article

Authors

1 Department of Biology, Faculty of Science, Payame Noor University, Tehran, Iran

2 Department of Biochemistry, Faculty of Biologilal Sciences, Tarbiat Modares University, Tehran, Iran

3 Department of Chemistry, Faculty of Sciences, University of Guilan, Rasht, Iran

4 Department of Biochemistry, Faculty of Biological Sciences, Tarbiat Modares University, Tehran, Iran

Abstract

For the first time in the present study the effects of vanillin, vanillyl alcohol, vanillic acid, as well as the newly synthesized vanillin derivative, bis-vanillin, were investigated on the oxidation of dopamine hydrochloride by mushroom tyrosinase. Among them, vanillin and bis-vanillin act as activators, while vanillyl alcohol and vanillic acid exhibited inhibitory effects, the IC50 values being estimated 1.5 and 1.0 mM, respectively. These compounds were mixed inhibitors. The presence of aldehyde and metoxy groups at the meta position of aromatic compounds seems to cause them to react as tyrosinase activators, as observed in the case of vanillin and bis-vanillin. The presence of both groups in bis-vanillin results in a stronger activation effect compared to vanillin. The results indicate that the electron-withdrawing capacity of the functional group at the C-1 position is essential for the inhibitory potency of vanillin derivatives. In comparison with other benzoic acid derivatives, the results obtained in this study suggest that the relative positioning of hydroxy and methoxy groups at meta and para positions plays an important role in the inhibition effects of benzoic acids and their inhibition potency.

Keywords


1. Prota G. Progress in the chemistry of melanins and related metabolites. Med Res Rev 1988;8:525-556.

2. Mayer AM. Polyphenol oxidases in plants and fungi: Going places? A review. Phytochemistry 2006;67:2318-2331.

3. Sánchez-Ferrer A, Rodríguez-López JN, García-Cánovas F, García-Carmona F. Tyrosinase: A comprehesive review of its mechanism. Biochim Biophys Acta 1995;1247:1-11.

4. Friedman M. Food browning and its prevention: An overview. J Agric Food Chem 1996;44:631-653.

5. Kubo I, Kinst-Hori I. Tyrosinase inhibitors from cumin. J Agric Food Chem 1998;46:5338-5341.

6. Kramer KJ,HopkinsTL. Tyrosinase metabolism for insect cuticle tanning. Arch Insect Biochem Physiol 1987;6:279-301.

7. Christensen BM, Li J, Chen C, Nappi AJ. Melanization immune responses in mosquito vectors. Trends Parasitol 2005;21:192-199.

8. Boss PK,GardnerRC, Janssen B, Ross GS. An apple polyphenol oxidase cDNA is up-regulated in wounded tissues. Plant Mol Biol 1995;27:429-433.

9. Ensminger AH, Ensminger ME, Konlande JE, Robson JRK. CRC Press.Boca Raton,LA1995.

10. Viterbo A, Yagen B, Mayer AM. Cucurbitacins, ‘attack’ enzymes and laccase in Botrytis cinerea. Phytochemistry 1992;32:61-65.

11. Pifferi PG, Baldassari L, Cultrera R. Inhibition by carboxylic acids of an o-diphenol oxidase from Prunus avium fruits. J Sci Food Agric 1974;25:263-270.

12. Maeda K, Fukuda M. In vitro effectiveness of several whitening cosmetic compounds in human melanocytes. J Soc Cosmet Chem 1991;42:361-368.

13. Huang XH, Chen QX, Wang Q, Song KK, Wang J, Sha L, Guan X. Inhibition of the activity of mushroom tyrosinase by alkylbenzoic acids. Food Chem 2006;94:1-6.

14. Jun N, Hong G, Jun K. Synthesis and evalution of 2',4',6'-trihydroxychalcones as a new class of tyrosine inhibitors.  Bioorg Med Chem 2007;15:2396-2402.

15. Xie JJ, Song KK, Qiu L, He Q, Huang H, Chen QX. Inhibitory effects of substrate analogues on enzyme activity and substrate specificities of mushroom tyrosinase. Food Chem 2007;103:1075-1079.

16. McEvily AJ, Iyengar R, Gross A. Inhibition of enzymatic browning in foods and beverages. U S patent 1991;32:253-273.

17. Rescigno A, Sollai F, Pisu B, Rinaldi A,  Sanjust E. Tyrosinase inhibition: general and applied aspects. J Enzym Inhib Med Chem 2002;17:207-218.

18. Noh JM,  Kwak SY,  Seo HS,  Seo JH,  Kim BG,  Lee YS. Kojic acid-amino acid conjugates as tyrosinase inhibitors. Bioorg Med Chem Lett 2009;19:5586-5589.

19. Kubo I, Kinst-Hori I, Kubo Y, Yamagiwa Y,  Kamikawa T, Haraguchi H.  Molecular design of antibrowning agents. J Agric Food Chem 2000;48:1393-1399.

20. Bradford MM. A rapid and sensitive for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 1976;72:248-54.

21. Robb DA. Tyrosinase. In: Lontie R (ed.) Copper proteins and copper enzymes, CRC Press. Boca Raton, FL, 1984; pp 207-240.

22. Zhang JP, Chen QX, Song KK, Xie JJ. Inhibitory effects of salicylic acid family compounds on the diphenolase activity of mushroom tyrosinase. Food Chem 2006; 95:579-584.

23. Copeland RA. Enzymes. Wiley-VCH, USA. 2000.

24. Akhtar M. SUSB-039, Suny Stony Brook, CHE 133Rev 12/06. 2008.

25. Irwin AP. Organic Syntheses. CV 4, 927. 1963.

26. Delomenede M, Bedos-Belval F, Duran H, Vindis C, Baltas M, Negre-Salvayre A. Development of novel antiatherogenic biaryls: design, synthesis, and reactivity. J Med Chem 2008;51:3171-3181.

27. Robit C, Rouch C, Cadet F. Inhibition of palmito (Axanthophoenix rubra) polyphenol oxidase by carboxylic acids. Food Chem 1997;59:355-360.

28. Kahn V, Ben-Shalom N. Zakin V. Effect of kojic acid on the oxidation of N-acetyldopamine by mushroom tyrosinase. J Agric and Food Chem. 1997;45:4460-4465.

29. Gao H, Nishida J, Saito SH, Kawabata J. Inhibitory effects of 5,6,7-trihydroxyflavones on tyrosinase. Molecules 2007;12:86-97.

30. Nerya O, Musa R, Khatib S, Tamir S, Vaya J. Chalcones as potent tyrosinase inhibitors: the effect of hydroxyl positions and numbers. Phytochemistry. 2004;65:1389-1395.

 31. Chen QX, Song KK, Qiu L, Liu XD, Huang H, Guo HY (2005) Inhibitory effects on mushroom tyrosinase by ρ-alkoxybenzoic acids. Food Chem 91:269-274

32. Chen QX, Song KK, Qiu L, Liu XD, Huang H, Guo HY. Inhibitory effects on mushroom tyrosinase by ρ-alkoxybenzoic acids. Food Chem 2005;91:269-274.

33. Likhitwitayawuid K. Stilbenes with tyrosinase inhibitory activity 2008:94:44-52.

34. Shimizu K, Kondo R, Sakai K. Inhibition of tyrosinase by flavonoids, stilbenes and related 4-substituted resorcinols: structure-activity investigations. Planta Med 2000;66:11-15.

35. Kubo I, Chen QX, Nihei KI, Calderon JS, Cespedes CL. Tyrosinase inhibition kinetics of anisic acid. Z Naturforsch C 2003;58:713-718