Journal of Microbiology and Biotechnology

The Korean Society for Microbiology and Biotechnology (한국미생물·생명공학회)
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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))
  • Received : 2018.04.04
  • Accepted : 2018.06.12
  • Published : 2018.07.28
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Abstract

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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References

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