Comparing the inhibitory abilities of epigallocatechin-3-gallate and gallocatechin gallate against tyrosinase and their combined effects with kojic acid. 2021

Xin Song, and Mengting Ni, and Ying Zhang, and Guowen Zhang, and Junhui Pan, and Deming Gong
State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang 330047, China.

Inhibition of tyrosinase activity contributes to the control of food browning and skin pigmentation diseases. Herein, the inhibitory mechanism of epigallocatechin-3-gallate (EGCG) and gallocatechin gallate (GCG) on tyrosinase were investigated. Both EGCG and GCG inhibited tyrosinase in a mixed manner with the IC50 values of 39.4 ± 0.54 μM and 36.8 ± 0.21 μM, and showed a synergism with their combination, while EGCG and GCG combined with kojic acid (IC50 = 19.2 ± 0.26 μM) exhibited antagonism and additive effect, respectively. EGCG and GCG interacted with tyrosinase mainly by hydrogen bonding and hydrophobic interactions and induced a looser conformation of tyrosinase. Molecular docking indicated that EGCG and GCG bound to the active center of tyrosinase and interacted with copper ions and key amino acid residues. Molecular dynamics simulation further characterized the structure and property of EGCG/GCG-tyrosinase complex. This study provides novel insights into the mechanism of catechins as tyrosinase inhibitors.

UI MeSH Term Description Entries
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D011753 Pyrones Keto-pyrans.
D002392 Catechin An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. Catechinic Acid,Catechuic Acid,(+)-Catechin,(+)-Cyanidanol,(+)-Cyanidanol-3,(-)-Epicatechin,(2R,3R)-2-(3,4-Dihydroxyphenyl)-3,5,7-chromanetriol,2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R-cis)-,3,3',4',5,7-Flavanpentol,Catergen,Cianidanol,Cyanidanol-3,Epicatechin,KB-53,Z 7300,Zyma,Cyanidanol 3,KB 53,KB53
D004357 Drug Synergism The action of a drug in promoting or enhancing the effectiveness of another drug. Drug Potentiation,Drug Augmentation,Augmentation, Drug,Augmentations, Drug,Drug Augmentations,Drug Potentiations,Drug Synergisms,Potentiation, Drug,Potentiations, Drug,Synergism, Drug,Synergisms, Drug
D006860 Hydrogen Bonding A low-energy attractive force between hydrogen and another element. It plays a major role in determining the properties of water, proteins, and other compounds. Hydrogen Bonds,Bond, Hydrogen,Hydrogen Bond
D014442 Monophenol Monooxygenase An enzyme of the oxidoreductase class that catalyzes the reaction between L-tyrosine, L-dopa, and oxygen to yield L-dopa, dopaquinone, and water. It is a copper protein that acts also on catechols, catalyzing some of the same reactions as CATECHOL OXIDASE. EC 1.14.18.1. Dopa Oxidase,Phenoloxidase,Tyrosinase,Cresolase,Phenol Oxidase,Phenoloxidase A,Phenoloxidase B,Monooxygenase, Monophenol,Oxidase, Dopa,Oxidase, Phenol
D062105 Molecular Docking Simulation A computer simulation technique that is used to model the interaction between two molecules. Typically the docking simulation measures the interactions of a small molecule or ligand with a part of a larger molecule such as a protein. Molecular Docking,Molecular Docking Simulations,Molecular Docking Analysis,Analysis, Molecular Docking,Docking Analysis, Molecular,Docking Simulation, Molecular,Docking, Molecular,Molecular Docking Analyses,Molecular Dockings,Simulation, Molecular Docking

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