Summary
Phenolic compounds such as chlorogenic acid, cryptochlorogenic acid, neochlorogenic acid and caffeic acid are widely distributed in fruits, vegetables and traditional Chinese medicines with a wide range of biological activities. Tyrosinase plays a critical role in the food industry, but recent studies have proposed unexplored aspects of clinical application. Tyrosinase-catalyzed oxidation of four polyphenols as well as its underlying mechanism remains unclear. In the current work, we investigated the kinetic properties of tyrosinase-catalyzed oxidation of the four polyphenols of interest. To measure the unstable o-quinone products, an analytical method using 3-methyl-2-benzothiazolinone hydrazone (MBTH) was established. The optimal incubation time, buffer pH, temperature and enzyme concentration for the enzyme activity in the presence of each polyphenol of interest were investigated. Under the final optimized conditions, the kinetics and substrate specificity of four polyphenols were examined. Kinetic data showed that tyrosinase had the greatest substrate affnity to chlorogenic acid compared with its isomers and caffeic acid. The catalytic effciency with chlorogenic acid was 8- to 15-fold higher than that with the other 3 polyphenols. Molecular docking study demonstrated that the tight binding of chlorogenic acid at the peripheral site should be the major reason for the specifcity to chlorogenic acid. In light of this, the rational design of high-affnity inhibitors against tyrosinase may focus on the binding of both the Cu site and peripheral site. This study will supply a basis for the selection of phenolic acids in food industry and health care.
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17 July 2020
The article ���Kinetic Characterization of Tyrosinase-catalyzed Oxidation of Four Polyphenols���, written by Wan-yu LIU, Congming ZOU, Jian-hua HU, Zi-jun XU, Lu-qin SI, Jun-jun LIU, Jian-geng HUANG, was originally published electronically on the publisher���s internet portal on May 2020 without open access. With the author(s)��� decision to opt for Open Choice, the copyright of the article is changed to �� The Author(s) 2020 and the article is forthwith distributed under a Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0/), which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.
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The original version of this article was revised due to a retrospective Open Access order.
The study was supported by grants from the National Natural Science Foundation of China (No. 81773811), Yunnan Applied Basic Research Project (No. 2017FB074), the Yunnan Provincial Tobacco Monopoly Bureau Grants (No. 2017YN09) and the Fundamental Research Funds for the Central Universities (No. 2020kfyXGYJ061).
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Liu, Wy., Zou, Cm., Hu, Jh. et al. Kinetic Characterization of Tyrosinase-catalyzed Oxidation of Four Polyphenols. CURR MED SCI 40, 239–248 (2020). https://doi.org/10.1007/s11596-020-2186-0
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DOI: https://doi.org/10.1007/s11596-020-2186-0