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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Agric. Food Chem. 2020, 68, 23, 6390-6394
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High Production of Ergothioneine in Escherichia coli using the Sulfoxide Synthase from Methylobacterium strains

  • Tomoyuki Kamide
    Tomoyuki Kamide
    Graduate School of Chemical Science and Engineering, Hokkaido University, N13-W8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan
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  • , 
  • Shun Takusagawa
    Shun Takusagawa
    Graduate School of Chemical Science and Engineering, Hokkaido University, N13-W8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan
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  • , 
  • Naoyuki Tanaka
    Naoyuki Tanaka
    Faculty of Life and Environmental Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8577, Japan
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  • , 
  • Yasushi Ogasawara
    Yasushi Ogasawara
    Graduate School of Engineering, Hokkaido University, N13-W8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan
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    Orcidhttp://orcid.org/0000-0002-3144-3985
  • , 
  • Yusuke Kawano
    Yusuke Kawano
    Faculty of Life and Environmental Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8577, Japan
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  • , 
  • Iwao Ohtsu
    Iwao Ohtsu
    Faculty of Life and Environmental Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8577, Japan
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  • , 
  • Yasuharu Satoh*
    Yasuharu Satoh
    Graduate School of Engineering, Hokkaido University, N13-W8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan
    *Email: [email protected]. Phone: +81-11-706-7818; Fax: +81-11-706-7818.
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    Orcidhttp://orcid.org/0000-0001-6671-7758
  • , and 
  • Tohru Dairi*
    Tohru Dairi
    Graduate School of Engineering, Hokkaido University, N13-W8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan
    *Email: [email protected]. Phone: +81-11-706-7815; Fax: +81-11-706-7118.
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    Orcidhttp://orcid.org/0000-0002-3406-7970
Cite this: J. Agric. Food Chem. 2020, 68, 23, 6390–6394
Publication Date (Web):May 21, 2020
https://doi.org/10.1021/acs.jafc.0c01846
Copyright © 2020 American Chemical Society
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    Abstract

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    We previously constructed a heterologous production system for ergothioneine (ERG) in Escherichia coli using five ERG biosynthesis genes (egtABCDE) from Mycobacterium smegmatis. However, significant amounts of hercynine (HER), an intermediate of ERG, as ERG were accumulated, suggesting that the reaction of EgtB catalyzing the attachment of γ-glutamylcysteine (γGC) to HER to yield hercynyl-γ-glutamylcysteine sulfoxide was a bottleneck. In this study, we searched for other EgtBs and found many egtB orthologs in diverse microorganisms. Among these, Methylobacterium strains possessed EgtBs that catalyze the direct conversion of HER into hercynylcysteine sulfoxide with l-cysteine (l-Cys) as a sulfur donor, in a manner similar to those of acidobacterial CthEgtB and fungal Egt1. An in vitro study with recombinant EgtBs from Methylobacterium brachiatum and Methylobacterium pseudosasicola clearly showed that both enzymes accepted l-Cys but not γGC. We reconstituted the ERG production system in E. coli with egtB from M. pseudosasicola; ERG productivity reached 657 mg L–1.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.jafc.0c01846.

    • Sodium dodecylsulfate-polyacrylamide gel electrophoresis (SDS-PAGE) analysis of Mb_EgtB and Mp_EgtB production (Figure S1); mass spectra of in vitro reaction products of l-Cys and recombinant EgtBs from M. brachiatum and M. pseudosasicola (Figure S2); comparison of various EgtB activities (Figure S3); effect of pH and temperature on Mp_EgtB activity (Figure S4); Michaelis–Menten plots of the Mp_EgtB for HER and l-Cys (Figure S5); Michaelis–Menten plots of the Mb_EgtB for HER and l-Cys (Figure S6); 1H NMR spectrum of HER (Figure S7); 13C NMR spectrum of HER (Figure S8); identities of amino acid sequences of type I–V EgtBs (Table S1); and primers used in this study (Table S2) (PDF)

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    Cited By

    This article is cited by 14 publications.

    1. Luwen Zhang, Jiawei Tang, Meiqing Feng, Shaoxin Chen. Engineering Methyltransferase and Sulfoxide Synthase for High-Yield Production of Ergothioneine. Journal of Agricultural and Food Chemistry 2023, 71 (1) , 671-679. https://doi.org/10.1021/acs.jafc.2c07859
    2. Mariia A. Beliaeva, Florian P. Seebeck. Discovery and Characterization of the Metallopterin-Dependent Ergothioneine Synthase from Caldithrix abyssi. JACS Au 2022, 2 (9) , 2098-2107. https://doi.org/10.1021/jacsau.2c00365
    3. Yibin Qiu, Zhonglin Chen, Erzheng Su, Libin Wang, Liang Sun, Peng Lei, Hong Xu, Sha Li. Recent Strategies for the Biosynthesis of Ergothioneine. Journal of Agricultural and Food Chemistry 2021, 69 (46) , 13682-13690. https://doi.org/10.1021/acs.jafc.1c05280
    4. Kexin Xiong, Hui Guo, Siyu Xue, Yiwei Dai, Liang Dong, Chaofan Ji, Sufang Zhang. Cost-effective production of ergothioneine using Rhodotorula mucilaginosa DL-X01 from molasses and fish bone meal enzymatic hydrolysate. Bioresource Technology 2024, 393 , 130101. https://doi.org/10.1016/j.biortech.2023.130101
    5. Jiaqi Xie, Yinghao Yu, Junjiang You, Zhiwei Ye, Fenglong Zhou, Na Wang, Jingru Zhong, Liqiong Guo, Junfang Lin. Ganoderma Fusions with High Yield of Ergothioneine and Comparative Analysis of Its Genomics. Journal of Fungi 2023, 9 (11) , 1072. https://doi.org/10.3390/jof9111072
    6. Kexin Xiong, Siyu Xue, Hui Guo, Yiwei Dai, Chaofan Ji, Liang Dong, Sufang Zhang. Ergothioneine: new functional factor in fermented foods. Critical Reviews in Food Science and Nutrition 2023, 58 , 1-12. https://doi.org/10.1080/10408398.2023.2185766
    7. Takashi Hirasawa, Yuki Shimoyamada, Yukio Tachikawa, Yasuharu Satoh, Yusuke Kawano, Tohru Dairi, Iwao Ohtsu. Ergothioneine production by Corynebacterium glutamicum harboring heterologous biosynthesis pathways. Journal of Bioscience and Bioengineering 2023, 135 (1) , 25-33. https://doi.org/10.1016/j.jbiosc.2022.10.002
    8. Bai-Xiong Chen, Ling-Na Xue, Tao Wei, Zhi-Wei Ye, Xue-Hai Li, Li-Qiong Guo, Jun-Fang Lin. Enhancement of ergothioneine production by discovering and regulating its metabolic pathway in Cordyceps militaris. Microbial Cell Factories 2022, 21 (1) https://doi.org/10.1186/s12934-022-01891-5
    9. Sean Doyle, Daragh D. Cuskelly, Niall Conlon, David A. Fitzpatrick, Ciara B. Gilmartin, Sophia H. Dix, Gary W. Jones. A Single Aspergillus fumigatus Gene Enables Ergothioneine Biosynthesis and Secretion by Saccharomyces cerevisiae. International Journal of Molecular Sciences 2022, 23 (18) , 10832. https://doi.org/10.3390/ijms231810832
    10. Douglas B. Kell, Etheresia Pretorius. The potential role of ischaemia–reperfusion injury in chronic, relapsing diseases such as rheumatoid arthritis, Long COVID, and ME/CFS: evidence, mechanisms, and therapeutic implications. Biochemical Journal 2022, 479 (16) , 1653-1708. https://doi.org/10.1042/BCJ20220154
    11. Liang‐Bin Xiong, Zhi‐Yong Xie, Jie Ke, Li Wang, Bei Gao, Xin‐Yi Tao, Ming Zhao, Ya‐Ling Shen, Dong‐Zhi Wei, Feng‐Qing Wang. Engineering Mycolicibacterium neoaurum for the production of antioxidant ergothioneine. Food Bioengineering 2022, 1 (1) , 26-36. https://doi.org/10.1002/fbe2.12004
    12. Steven A. van der Hoek, Matej Rusnák, Guokun Wang, Lyubomir Dimitrov Stanchev, Luana de Fátima Alves, Mathew M. Jessop-Fabre, Kalaivani Paramasivan, Irene Hjorth Jacobsen, Nikolaus Sonnenschein, José L. Martínez, Behrooz Darbani, Douglas B. Kell, Irina Borodina. Engineering precursor supply for the high-level production of ergothioneine in Saccharomyces cerevisiae. Metabolic Engineering 2022, 70 , 129-142. https://doi.org/10.1016/j.ymben.2022.01.012
    13. Irwin K. Cheah, Barry Halliwell. Ergothioneine, recent developments. Redox Biology 2021, 42 , 101868. https://doi.org/10.1016/j.redox.2021.101868
    14. Yiwen Han, Xiuyang Tang, Yuting Zhang, Xuechao Hu, Lu-Jing Ren. The current status of biotechnological production and the application of a novel antioxidant ergothioneine. Critical Reviews in Biotechnology 2021, 41 (4) , 580-593. https://doi.org/10.1080/07388551.2020.1869692
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