Biotechnology and Bioprocess Engineering 2022; 27(2): 253-261  
Production of Theasinensin A Using Laccase as Antioxidant and Antiaging Agent
Jinkyung Choi, Eun-Mi Kim, Byung Joon Ko, Uk-Jae Lee, Joo-Hyun Seo, and Byung-Gee Kim
Jinkyung Choi, Uk-Jae Lee, Byung-Gee Kim*
School of Chemical and Biological Engineering, Seoul National University, Seoul 08826, Korea
Tel: +82-2-880-6774; Fax: +82-2-872-7528
E-mail: byungkim@snu.ac.kr
Eun-Mi Kim
R&D Unit, Amorepacific Corporation, Yongin 17074, Korea
Byung Joon Ko
School of Biopharmaceutical and Medical Sciences, Sungshin Women’s University, Seoul 02844, Korea
Joo-Hyun Seo*
Department of Bio and Fermentation Convergence Technology, Kookmin University, Seoul 02707, Korea
Tel: +82-2-910-5736; Fax: +82-2-910-5739
E-mail: joohyunseo@kookmin.ac.kr
Byung-Gee Kim
School of Chemical and Biological Engineering and Interdisciplinary Program in Bioengineering, Seoul National University, Seoul 08826, Korea
Jinkyung Choi and Eun-Mi Kim contributed equally to this work.
Received: May 23, 2021; Revised: July 11, 2021; Accepted: July 13, 2021; Published online: April 30, 2022.
© The Korean Society for Biotechnology and Bioengineering. All rights reserved.

This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract
Epigallocatechin-3-O-gallate (EGCG), one of the most abundant monomeric catechin compounds in green tea, was oxidized to EGCG dimers through radical oxidative reaction using laccase, a member of the tea polyphenol oxidase family. Electrospray ionization tandem LC-MS (ESI-LC/MS) was applied for the characterization of the dimers, including theacitrin, dehydrotheasinensin, and theasinensin, which were produced by the radical oxidative reaction. Chemical structures of the EGCG dimer were identified using LC/MS/MS and fragmentation patterns of EGCG dimer. The dimers were isomerized by heat treatment at 80°C after oxidation step to mimic heat treatment and drying in the last step of leaf fermentation. As a result of the heat treatment, theasinensin A (TSA) was formed as a major dimer product. After the two steps of Sephadex LH-20 and C18 column chromatography, 27.6mg of purified TSA was obtained from 485.4 mg of dried reaction mixture. Biological effect of TSA as antioxidant and anti-aging effects were investigated. Purified TSA significantly suppressed the expression of ultraviolet Binduced matrix metalloproteinase-1 in human fibroblast (HS68 cell), indicating the potential use of TSA as antioxidant and anti-aging agent.
Keywords: catechins, epigallocatechin-3-gallate, theasinensin A, polyphenol oxidase, matrix metalloproteinase-1


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