Quercetin Fatty Acid Esters: from Synthesis to the Mushroom Tyrosinase Inhibition
Subject Areas : Journal of Chemical Health RisksZohreh Jamali 1 , Golam Reza Rezaei Behbahan 2 , Karim Zare 3 , Nematollah Gheibi 4
1 - Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran
2 - Department of Chemistry, Imam Khomeini International University, Qazvin, Iran
3 - Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran
4 - Cellular and Molecular Research Center, Qazvin University of Medical Sciences, Qazvin, Iran
Keywords: Instability, Inhibition, Quercetin, Mushroom tyrosinase, PUFA,
Abstract :
New complexes of quercetin esterification with alpha linolenic acid (ALA) and linoleic acid (LA) were applied as inhibitor of tyrosinase as the main melanogenesis.enzyme The most abundant flavonoid compound, quercetin was considered as the base of esterification with poly unsaturated fatty acids (PUFA). The new derivatives including quercetin- ALA (complex I) and quercetin- LA (complex II) were designed and their impacts on mushroom tyrosinase (MT) were assessed by experimental and theoretical studies. The new complexes I and II were induced competitive inhibition on tyrosinase enzyme with Ki of 0.59 and 0.40 mM, respectively. The molecular analysis of docking revealed that the complex II has a better ability to interact with enzyme than the complex I and the nature of interactions was obeyed from hydrophobic manner. So, the esterification of quercetin by above mentioned fatty acids achieved strength inhibitors against tyrosinase and because of their abundant in natural sources and importance in lifestyle, it is proposed to utilize them in medicine, cosmetics, agriculture and food industries. Their other biological properties need more investigations.
1. Chen Q.X., Kubo I., 2002. Kinetics of mushroom tyrosinase inhibition by quercetin. J Agric Food Chem. 50(14), 4108- 4112.
2. Uddin Zaidi K., S Ali A., A Ali S., Nazz I., 2014. Microbial Tyrosinases: Promising Enzymes for Pharmaceutical, Food Bioprocessing, and Environmental Industry. Journal of Biochemistry Research International. Article ID 854687, 16 pages. http: //dx. doi.org/ 10. 1155/2014/ 854687.
3. Lee H.S., 2002. Tyrosinase inbibitors of pulsatilla cernua root-derived materials. J Agric Food Chem. 50(6), 1400- 1403.
4. Liangli Y.U., 2003. Inhibitory effects of (S) - and I-6-hydroxy-2, 5, 7, 8-tetramethylchroman-2-carboxylic acids on tyrosinase activity. J Agric Food Chem. 51(8), 2344-2347.
5. Yun-Ji G., Zhi-Zhen P., Chao-Qi C., Yong-Hua H., Feng-Jiao L., Yan S., Jiang-Hua Y., Qing-Xi C., 2010. Inhibitory Effects of Fatty Acids on the Activity of Mushroom Tyrosinase. J Appl Biochem Biotechnol. 162(6), 1564–1573.
6. Gheibi N., Hosseini Zavareh S., Rezaei Behbahani G.R., Haghbeen K., Sirati-sabet M., Ilghari D., Goodarzvand Chegini K., 2016. Comprehensive kinetic and structural studies of different flavonoids inhibiting diphenolase activity of mushroom tyrosinase. J Applied biochemistry and microbiology. 52(3), 304-310.
7. NematiNiko F., Goodarzvand Chegini K., Asghari H., Amini A., Gheibi N., 2017. Modifying effects of carboxyl group on the interaction of recombinant S100A8/A9 complex with tyrosinase. J Biochimica et Biophysica Acta. 1865(3), 370–379.
8. Zanotti I., Dall’Asta M., Mena P., Mele L., Bruni R., Ray S., Del Rio D. 2015. Atheroprotective effects of [poly] phenols: A focus on cell cholesterol metabolism. J Food Funct. 6(1), 13–31.
9. Williamson G., 2017. The role of polyphenols in modern nutrition. J Nutr Bull. 42(3), 226–235.
10. Van Dam R.M., Naidoo N., Landberg R., 2013. Dietary flavonoids and the development of type 2 diabetes and cardiovascular diseases: Review of recent findings. J Curr Opin Lipidol. 24(1), 25–33.
11. Vogiatzoglou A., Heuer T., Mulligan A.A., Lentjes M.A.H., Luben R.N., Kuhnle G.G.C., 2014. Estimated dietary intakes and sources of flavanols in the German population (German National Nutrition Survey II). Eur J Nutr. 53(2), 635–643.
12.Gerard H., 2001. Importance of polyunsaturated fatty acids of the n-6 and n-3 families for early human development. Eur J Lipid Sci. Technol.103(6),379–389.
13. Mu-Hyoung L., Hyun-Jin K., Dong-Ju H., Jong-Hyun P., Hong-Yong K., 2002. Therapeutic Effect of Topical Application of Linoleic Acid and Lincomycin in Combination with Betamethasone Valerate in Melasma Patients. J The Korean Academy of Medical Sciences. 17(4), 518-23.
14. Hideya A., Atsuko R., Akira H., Masahiro O., Masamitsu I., 1998. Linoleic acid and á-linolenic acid lightens ultraviolet-induced Hyperpigmentation of the skin. J Arch Dermatol Res. 290(7), 375–381.
15. Ha K.M., Kim J.A., Park D., Kim J.M., Chung K.W., 2011. Analogs of 5‐ (substituted benzylidene)hydantoin as inhibitors of tyrosinase and melanin formation. Journal of Biochimica et Biophysica Acta. 1810(6), 612-616.
16. Gheibi N., Saboury A., Mansuri-Torshizi H., Haghbeen K., Moosavi-Movahedi A., 2005. The inhibition effect of some n-alkyl dithiocarbamates on mushroom tyrosinase. J Enzyme inhibition and medicinal chemistry. 20(4), 393-399.
17. Gheibi N., Saboury A.A., Haghbeen K., Rajaei F., Pahlevan A.A., 2009. Dual effects of aliphatic carboxylic acids on cresolase and catecholase reactions of mushroom tyrosinase.Journal of Enzyme Inhibition and Medicinal Chemistry. 24(5), 1076–1081.
18. Jiang-ning H., Xian-guo Z., Yi H., Fang C., Ze-yuan D., 2016. Esterification of Quercetin Increases Its Transport Across Human Caco-2 Cells. Journal of Food Science. 81(7), 1825-1832.
19. Gheibi N., Jamali Z., Rezaei Behbahani G.R., Zare K., 2018. Effect of chrysin omega‐3 and 6 fatty acid esters on mushroom tyrosinase activity, stability, and structure. Journal of Food Biochem. DOI: 10.1111/jfbc.12728.
20. Gheibi N., Saboury A., Haghbeen K., Rajaei F., Pahlevan A., 2009. Dual effects of aliphatic carboxylic acids on cresolase andcatecholase reactions of mushroom tyrosinase. J Enzyme Inhib Med Chem. 24(5), 1076-1081.
21. Gheibi N., Taherkhani N., Ahmadi A., Haghbeen K., Ilghari D., 2015. Characterization of inhibitory effects of the potential therapeutic inhibitors, benzoic acid and pyridine derivatives, on the monophenolase and diphenolase activities of tyrosinase. Iranian Journal of Basic Medical Sciences. 18(2), 122-129.
22. Fiser A., Do R.K., Sali A., 2000. Modeling of loops in protein structures. J Protein Science. 9(9), 1753-1773.
23. Sanner M.F., 1999. Python: a programming language for software integration and development. J Mol Graph Model. 17(1), 57-61.
24. Voityuk A.A., Anton J., Stasyuk A.J., Vyboishchikov S.F., 2018. A simple model for calculating atomic charges in molecules. Journal of Physical Chemisty Chemical Physics. 20(36), 1-10.
25. Bjelkmar P., Larsson P., Cuendet M.A., Hess B., Lindahl E., 2010. Implementation of the CHARMM Force Field in GROMACS: Analysis of Protein Stability Effects from Correction Maps, Virtual Interaction Sites, and Water Models. J Chemical Theory and Computation. 6(2), 459-466.
26. Trott O., Olson A.J., 2010. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization and multithreading. J Computational Chemistry. 31(2), 455-461.
27. Medina-Franco J.L., Méndez-Lucio O., Martinez-Mayorga K., 2014. Chapter One - The Interplay Between Molecular Modeling and Chemoinformatics to Characterize Protein–Ligand and Protein–Protein Interactions Landscapes for Drug Discovery: Advances in Protein Chemistry and Structural Biology. 96, 1-37.
28. NematiNiko F., Goodarzvand Chegini K., Asghari H., Amini A., Gheibi N., 2017. Modifying effects of carboxyl group on the interaction of recombinant S100A8/A9 complex with tyrosinase. J Biochimica et Biophysica Acta. 1865(3), 370–379.
29. Van Dijk M., Wassenaar T.A., Bonvin A.M., 2012. A Flexible, Grid-Enabled Web Portal for GROMACS Molecular Dynamics Simulations. J Chemical Theory and Computation. 8(10), 3463-3472.
30. Saik A.Y.H., Stansla J., Choo W.S., 2017. Enzymatic synthesis of quercetin oleate esters using Candida antarctica lipase B , Biotechnol Lett. 39(2), 297-304.
31.Moussou P., Falcimaigne A., Ghoul M., Danous L., Pauly G., 2005. Esters of flavonoids with ω-substituted C6-C22 fatty acids. WIPO Patent WO/2005/000831A1.
32. Sudhanshu S., Vasantha H., 2015. Antiproliferative activity of long chain acylated esters of quercetin-3-O-glucoside in hepatocellular carcinoma HepG2 cells. J Experimental Biology and Medicine. 240(11), 1452–1464.
33. Slavin J.L., Lioyd B., 2012. Health benefits of fruit and vegtables. Journal of Advances in Nutrition. 3(4), 506- 516.
34. Gheibi N., Ilghari D., Shivani M., Hosseini Zavareh S., Rezaei Behbehani G., Taherkhani N., Piri,H., 2014. The effect of gallic acid, naringin, chrysin and quercetin as flavonoids, on the thermodynamic stability of tyrosinase. J Curr Res Chem Pharma Sci. 1(10), 14–21.
35. Chebil L., Humeau C., Falcimaigne A., Engasser J.M., Ghoul M., 2006. Enzymatic acylation of flavonoids. J Process Biochemistry. 41(11), 2237–2251.