Antioxidant Potential and Tyrosinase Inhibitory Properties of Quebecol as Natural Phenolic Compound

Öz

In this paper, we investigated the antioxidant potential of Quebecol in vitro using several assays. These; Cu2+-Cu+ reducing, DPPH• scavenging, Fe3+-Fe2+reducing, ABTS•+ scavenging. The IC50 amounts of the Quebecol in the DPPH• and ABTS•+ methods were 14.78 and 5.38 μg m1, respectively. Tyrosinase enzyme is a functional oxidase that is extensively divided in nature. It is the main enzyme in melanin synthesis and also is involved in designating the color of mammalian hair and skin. Recently, there has been a remarkable concern to study the inhibitory activity of the tyrosinase enzyme and some inhibitory molecules isolated from natural sources. For tyrosinase enzyme, Quebecol and kojic Acid (Standard) as natural phenols have IC50 values of 4.64 and 9.28 μM.

Anahtar Kelimeler

• Quebecol
• antioxidant activity
• tyrosinase
• enzyme inhibition

Kaynakça

1. Apak R, Güçlü K, Demirata B, Özyürek M, Esin Çelik S, Bektaşoğlu B, Işıl Berker K, Özyurt D. 2007. Comparative evaluation of various total antioxidant capacity assays applied to phenolic compounds with the CUPRAC assay. Molecules, 12: 1496-1547.
2. Ball DW. 2007. The Chemical Composition of Maple Syrup. J. Chem. Edu. 84: 1647
3. Chen J, Liu S, Huang Z, Huang W, Li Q, Ye Y. 2017. Molecular inhibitory mechanism of dihydromyricetin on mushroom tyrosinase. Journal of Biomolecular Structure and Dynamics. 1-13
4. Elmastaş M, Gülçin İ, Beydemir Ş, Küfrevioğlu Öİ, Aboul-Enein HY. 2006. Radical scavenging activity and antioxidant capacity of bay leaf extracts. Analytical Letters, 39: 47-65.
5. Elmastaş M, Gülçin İ, Öztürk L, Gökçe İ. 2005. Investigation of antioxidant properties of spearmint (Mentha spicata L.). Asian Journal of Chemistry, 17: 137-148.
6. Espín J.C, and Wichers HJ. 1999. Slow-binding inhibition of mushroom (Agaricus bisporus) tyrosinase isoforms by tropolone. Journal of Agricultural and Food Chemistry, 47 (7): 2638–2644.
7. Gülçin İ, 2005. The antioxidant and radical scavenging activities of black pepper (Piper nigrum) seeds. International Journal of Food Sciences and Nutrition, 56: 491-499.
8. Gülçin İ, Berashvili D, Gepdiremen A. 2005a. Antiradical and antioxidant activity of total anthocyanins from Perilla pankinensis decne. Journal of Ethnopharmacology, 101: 287-293.

9. Gülçin İ, Beydemir Ş, Alici HA, Elmastaş M, Büyükokuroğlu ME, 2004a. In vitro antioxidant properties of morphine. Pharmacological Research, 49: 59-66.
10. Gülçin İ, Beydemir Ş, Hisar O. 2005b. The effect of α-tocopherol on the antioxidant enzymes activities and lipid peroxidation of rainbow trout (Oncorhynchus mykiss), Acta Veterinaria Hungarica, 53: 425-433.
11. Gülçin İ, Beydemir Ş, Şat İG, Küfrevioğlu Öİ. 2005c. Evaluation of antioxidant activity of cornelian cherry (Cornus mas L.). Acta Aliment Hung. 34: 193-202.
12. Gülçin İ, Elias R, Gepdiremen A, Boyer L. 2006a. Antioxidant activity of lignans from fringe tree (Chionanthus virginicus L.). European Food Research. 223: 759-767.
13. Gülçin İ, Küfrevioğlu Öİ, Oktay M, Büyükokuroğlu ME, 2004b. Antioxidant, antimicrobial, antiulcer and analgesic activities of nettle (Urtica dioica L.). Journal of Ethnopharmacology, 90: 205-215.
14. Gülçin İ, Mshvildadze V, Gepdiremen A, Elias R. 2006b. Screening of antiradical and antioxidant activity of monodesmosides and crude extract from Leontice smirnowii tuber. Phytomedicine, 13: 343-351.
15. Gülçin İ, Şat İG, Beydemir Ş, Küfrevioğlu Öİ, 2004c. Evaluation of the in vitro antioxidant properties of extracts of broccoli (Brassica oleracea L.). Italian Journal of Food Sciences, 16 (1): 17-30.
16. Gülçin İ, Tel AZ, Kirecci E. 2008. Antioxidant, antimicrobial, antifungal and antiradical activities of Cyclotrichium niveum (Boiss.) Manden and Scheng. International Journal of Food Properties, 11: 450-471.
17. Gülçin İ. 2006. Antioxidant and Antiradical Activities of L-Carnitine. Life Sciences, 78: 803–811.
18. Gülçin İ. 2006. Antioxidant activity of caffeic acid (3,4-dihydroxycinnamic acid). Toxicology, 217: 213-220.
19. Gülçin İ. 2008. Measurement of antioxidant ability of melatonin and serotonin by the DMPD and CUPRAC methods as trolox equivalent. Journal of Enzyme Inhibition and Medicinal Chemistry, 23: 871-876.
20. Huang XH, Chen QX, Wang Q, Song KK, Wang J, Sha L, Guan X. 2006. Inhibition of the activity of mushroom tyrosinase by alkylbenzoic acids Food Chemistry, 94: 1-6
21. Ishioka W, Oonuki S, Iwadate T, Nihei K. 2019. Resorcinol alkyl glucosides as potent tyrosinase inhibitors. Bioorganic & Medicinal Chemistry Letters, 29(2): 313–316.
22. Köksal E, Gülçin İ, Öztürk Sarıkaya SB, Bursal E. 2009. On the in vitro antioxidant activity of silymarin. Journal of Enzyme Inhibition and Medicinal Chemistry, 24: 395–405.
23. Köksal E, Gülçin İ. 2008. Antioxidant activity of cauliflower (Brassica oleracea L.). Turkish Journal of Agriculture and Forestry, 32: 65-78.
24. Li L, Seeram NP. 2011. Quebecol, a novel phenolic compound isolated from Canadian maple syrup. Journal of Functional Foods. 3: 125-128.
25. Matsumoto T, Nakajima T, Iwadate T, Nihei K. 2018. Chemical synthesis and tyrosinase-inhibitory activity of isotachioside and its related glycosides. Carbohydrate Research, 465: 22–28.
26. Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. 1999. Antioxidant activity applying an improved ABTS radical cation decolorization assay. 26: 1231-1237.
27. Ros JR, Rodríguez-López JN, García-Cánovas F. 1993. Effect of L-ascorbic acid on the monophenolase activity of tyrosinase. Biochemistry Journal, 295: 309-312
28. Tanaka Y, Suzuki M, Kodachi Y, Nihei K. 2019. Molecular design of potent, hydrophilic tyrosinase inhibitors based on the natural dihydrooxyresveratrol skeleton. Carbohydrate Research, 472: 42-49.
29. Wang T, Zhang G, Yan J, Gong D. 2014. Inhibitory effect of morin on tyrosinase: insights from spectroscopic and molecular docking studies. Food Chemistry., 163: 226-233
30. Zolghadri S, Bahrami A, Hassan Khan MT, Munoz-Munoz J, Garcia-Molina F, Garcia-Canovas F, Saboury AA. 2019. A comprehensive review on tyrosinase inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry, 34 (1): 279–309.