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Production of Theasinensin A Using Laccase as Antioxidant and Antiaging Agent

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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, 27.6 mg 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 B-induced matrix metalloproteinase-1 in human fibroblast (HS68 cell), indicating the potential use of TSA as antioxidant and anti-aging agent.

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Acknowledgements

This work was supported by the Ministry of Science, ICT and Future Planning (NRF-2017R1E1A1A01073523). Joo-Hyun Seo was supported by Korea Environmental Industry and Technology Institute (KEITI) grant funded by the Ministry of Environment of Korea and the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIT) (No. 2020R1F1A1057135).

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Author notes

  1. Jinkyung Choi and Eun-Mi Kim contributed equally to this work.

Authors and Affiliations

  1. School of Chemical and Biological Engineering, Seoul National University, Seoul, 08826, Korea

    Jinkyung Choi, Uk-Jae Lee & Byung-Gee Kim

  2. R&D Unit, Amorepacific Corporation, Yongin, 17074, Korea

    Eun-Mi Kim

  3. School of Biopharmaceutical and Medical Sciences, Sungshin Women’s University, Seoul, 02844, Korea

    Byung Joon Ko

  4. Department of Bio and Fermentation Convergence Technology, Kookmin University, Seoul, 02707, Korea

    Joo-Hyun Seo

  5. School of Chemical and Biological Engineering and Interdisciplinary Program in Bioengineering, Seoul National University, Seoul, 08826, Korea

    Byung-Gee Kim

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  1. Jinkyung Choi
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Correspondence to Joo-Hyun Seo or Byung-Gee Kim.

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Choi, J., Kim, EM., Ko, B.J. et al. Production of Theasinensin A Using Laccase as Antioxidant and Antiaging Agent. Biotechnol Bioproc E 27, 253–261 (2022). https://doi.org/10.1007/s12257-021-0145-7

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  • DOI: https://doi.org/10.1007/s12257-021-0145-7

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