Journal of Microbiology and Biotechnology

  • 제28권7호
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  • Pages.1105-1111
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  • 2018
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  • 1017-7825(pISSN)
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  • 1738-8872(eISSN)
한국미생물·생명공학회 (The Korean Society for Microbiology and Biotechnology)
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Production of Bioactive 3'-Hydroxystilbene Compounds Using the Flavin-Dependent Monooxygenase Sam5

  • Heo, Kyung Taek (Anticancer Agents Research Center, Korea Research Institute of Bioscience and Biotechnology (KRIBB)) ;
  • Lee, Byeongsan (Anticancer Agents Research Center, Korea Research Institute of Bioscience and Biotechnology (KRIBB)) ;
  • Son, Sangkeun (Anticancer Agents Research Center, Korea Research Institute of Bioscience and Biotechnology (KRIBB)) ;
  • Ahn, Jong Seog (Anticancer Agents Research Center, Korea Research Institute of Bioscience and Biotechnology (KRIBB)) ;
  • Jang, Jae-Hyuk (Anticancer Agents Research Center, Korea Research Institute of Bioscience and Biotechnology (KRIBB)) ;
  • Hong, Young-Soo (Anticancer Agents Research Center, Korea Research Institute of Bioscience and Biotechnology (KRIBB))
  • 투고 : 2018.04.04
  • 심사 : 2018.06.12
  • 발행 : 2018.07.28
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초록

The flavin-dependent monooxygenase Sam5 was previously reported to be a bifunctional hydroxylase with coumarate 3-hydroxylase and resveratrol 3'-hydroxylase activities. In this article, we showed the Sam5 enzyme has 3'-hydroxylation activities for methylated resveratrols (pinostilbene and pterostilbene), hydroxylated resveratrol (oxyresveratrol), and glycosylated resveratrol (piceid) as substrates. However, piceid, a glycone-type stilbene used as a substrate for bioconversion experiments with the Sam5 enzyme expressed in Escherichia coli, did not convert to the hydroxylated compound astringin, but it was converted by in vitro enzyme reactions. Finally, we report a novel catalytic activity of Sam5 monooxygenase for the synthesis of piceatannol derivatives, 3'-hydroxylated stilbene compounds. Development of this bioproduction method for the hydroxylation of stilbenes is challenging because of the difficulty in expressing P450-type hydroxylase in E. coli and regiospecific chemical synthesis.

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참고문헌

  1. Pandey BP, Lee N, Choi KY, Jung E, Jeong DH, Kim BG. 2011. Screening of bacterial cytochrome P450s responsible for regiospecific hydroxylation of (iso)flavonoids. Enzyme Microb. Technol. 48: 386-392. https://doi.org/10.1016/j.enzmictec.2011.01.001
  2. Kim DH, Ahn T, Jung HC, Pan JG, Yun CH. 2009. Generation of the human metabolite piceatannol from the anticancer-preventive agent resveratrol by bacterial cytochrome P450 BM3. Drug Metab. Dispos. 37: 932-936. https://doi.org/10.1124/dmd.108.026484
  3. Furuya T, Kino K. 2014. Regioselective synthesis of piceatannol from resveratrol: catalysis by two-component flavin-dependent monooxygenase HpaBC in whole cells. Tetrahedron Lett. 55: 2853-2855. https://doi.org/10.1016/j.tetlet.2014.03.076
  4. Lin Y, Yan Y. 2014. Biotechnological production of plantspecific hydroxylated phenylpropanoids. Biotechnol. Bioeng. 111: 1895-1899. https://doi.org/10.1002/bit.25237
  5. Furuya T, Sai M, Kino K. 2016. Biocatalytic synthesis of 3,4,5,3',5'-pentahydroxy-trans-stilbene from piceatannol by two-component flavin-dependent monooxygenase HpaBC. Biosci. Biotechnol. Biochem. 80: 193-198. https://doi.org/10.1080/09168451.2015.1072463
  6. Lin Y, Yan Y. 2012. Biosynthesis of caffeic acid in Escherichia coli using its endogenous hydroxylase complex. Microb. Cell Fact. 11: 42. https://doi.org/10.1186/1475-2859-11-42
  7. Prieto MA, Perez-Aranda A, Garcia JL. 1993. Characterization of an Escherichia coli aromatic hydroxylase with a broad substrate range. J. Bacteriol. 175: 2162-2167. https://doi.org/10.1128/jb.175.7.2162-2167.1993
  8. Heo KT, Kang S-Y, Jang J-H, Hong Y-S. 2017. Sam5, a coumarate 3-hydroxylase from Saccharothrix espanaensis: new insight into the piceatannol production as a resveratrol 3'- hydroxylase. ChemistrySelect 2: 8785-8789. https://doi.org/10.1002/slct.201701969
  9. Surh YJ. 2003. Cancer chemoprevention with dietary phytochemicals. Nat. Rev. Cancer 3: 768-780. https://doi.org/10.1038/nrc1189
  10. Potter GA, Patterson LH, Wanogho E, Perry PJ, Butler PC, Ijaz T, et al. 2002. The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1. Br. J. Cancer 86: 774-778. https://doi.org/10.1038/sj.bjc.6600197
  11. Piotrowska H, Kucinska M, Murias M. 2012. Biological activity of piceatannol: leaving the shadow of resveratrol. Mutat. Res. 750: 60-82. https://doi.org/10.1016/j.mrrev.2011.11.001
  12. Kwon JY, Seo SG, Heo YS, Yue S, Cheng JX, Lee KW, et al. 2012. Piceatannol, natural polyphenolic stilbene, inhibits adipogenesis via modulation of mitotic clonal expansion and insulin receptor-dependent insulin signaling in early phase of differentiation. J. Biol. Chem. 287: 11566-11578. https://doi.org/10.1074/jbc.M111.259721
  13. Ullrich R, Hofrichter M. 2007. Enzymatic hydroxylation of aromatic compounds. Cell. Mol. Life Sci. 64: 271-293. https://doi.org/10.1007/s00018-007-6362-1
  14. Cheng TC, Lai CS, Chung MC, Kalyanam N, Majeed M, Ho CT, et al. 2014. Potent anti-cancer effect of 3'-hydroxypterostilbene in human colon xenograft tumors. PLoS One 9: e111814. https://doi.org/10.1371/journal.pone.0111814
  15. Kim YM, Yun J, Lee CK, Lee H, Min KR, Kim Y. 2002. Oxyresveratrol and hydroxystilbene compounds. Inhibitory effect on tyrosinase and mechanism of action. J. Biol. Chem. 277: 16340-16344. https://doi.org/10.1074/jbc.M200678200
  16. Dziggel C, Schafer H, Wink M. 2017. Tools of pathway reconstruction and production of economically relevant plant secondary metabolites in recombinant microorganisms. Biotechnol. J. 12: 1600145. https://doi.org/10.1002/biot.201600145
  17. Kang SY, Lee JK, Jang JH, Hwang BY, Hong YS. 2015. Production of phenylacetyl-homoserine lactone analogs by artificial biosynthetic pathway in Escherichia coli. Microb. Cell Fact. 14: 191. https://doi.org/10.1186/s12934-015-0379-1
  18. Diaz E, Ferrandez A, Prieto MA, Garcia JL. 2001. Biodegradation of aromatic compounds by Escherichia coli. Microbiol. Mol. Biol. Rev. 65: 523-569. https://doi.org/10.1128/MMBR.65.4.523-569.2001
  19. Spyrou G, Haggard-Ljungquist E, Krook M, Jornvall H, Nilsson E, Reichard P. 1991. Characterization of the flavin reductase gene (fre) of Escherichia coli and construction of a plasmid for overproduction of the enzyme. J. Bacteriol. 173: 3673-3679. https://doi.org/10.1128/jb.173.12.3673-3679.1991
  20. Choi O, Lee JK, Kang SY, Pandey RP, Sohng JK, Ahn JS, et al. 2014. Construction of artificial biosynthetic pathways for resveratrol glucoside derivatives. J. Microbiol. Biotechnol. 24: 614-618. https://doi.org/10.4014/jmb.1401.01031
  21. Henry C, Vitrac X, Decendit A, Ennamany R, Krisa S, Merillon JM. 2005. Cellular uptake and efflux of trans-piceid and its aglycone trans-resveratrol on the apical membrane of human intestinal Caco-2 cells. J. Agric. Food Chem. 53: 798-803. https://doi.org/10.1021/jf048909e
  22. Day AJ, DuPont MS, Ridley S, Rhodes M, Rhodes MJ, Morgan MR, et al. 1998. Deglycosylation of flavonoid and isoflavonoid glycosides by human small intestine and liver beta-glucosidase activity. FEBS Lett. 436: 71-75. https://doi.org/10.1016/S0014-5793(98)01101-6
  23. Mikstacka R, Przybylska D, Rimando AM, Baer-Dubowska W. 2007. Inhibition of human recombinant cytochromes P450 CYP1A1 and CYP1B1 by trans-resveratrol methyl ethers. Mol. Nutr. Food Res. 51: 517-524. https://doi.org/10.1002/mnfr.200600135
  24. Wilson MA, Rimando AM, Wolkow CA. 2008. Methoxylation enhances stilbene bioactivity in Caenorhabditis elegans. BMC Pharmacol. 8: 15. https://doi.org/10.1186/1471-2210-8-15
  25. Nutakul W, Sobers HS, Qiu P, Dong P, Decker EA, McClements DJ, Xiao H. 2011. Inhibitory effects of resveratrol and pterostilbene on human colon cancer cells: a side-byside comparison. J. Agric. Food Chem. 59: 10964-10970. https://doi.org/10.1021/jf202846b
  26. Rimando AM, Cuendet M, Desmarchelier C, Mehta RG, Pezzuto JM, Duke SO. 2002. Cancer chemopreventive and antioxidant activities of pterostilbene, a naturally occurring analogue of resveratrol. J. Agric. Food Chem. 50: 3453-3457. https://doi.org/10.1021/jf0116855

피인용 문헌

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