Biocatalytic synthesis of 3,4,5,3',5'-pentahydroxy-trans-stilbene from piceatannol by two-component flavin-dependent monooxygenase HpaBC

Toshiki Furuya, Masahiko Sai, Kuniki Kino

    Research output: Contribution to journalArticle

    7 Citations (Scopus)

    Abstract

    HpaBC monooxygenase was previously reported to hydroxylate resveratrol to piceatannol. In this article, we report a novel catalytic activity of HpaBC for the synthesis of a pentahydroxylated stilbene. When Escherichia coli cells expressing HpaBC were incubated with resveratrol, the resulting piceatannol was further converted to a new product. This product was identified by mass spectrometry and NMR spectroscopy as a 5-hydroxylated piceatannol, 3,4,5,3',5'-pentahydroxy-trans-stilbene (PHS), which is a reportedly valuable biologically active stilbene derivative. We attempted to produce PHS from piceatannol on a flask scale. After examining the effects of detergents and buffers on PHS production, E. coli cells expressing HpaBC efficiently hydroxylated piceatannol to PHS in a reaction mixture containing 1.5% (v/v) Tween 80 and 100mM 3-morpholinopropanesulfonic acid-NaOH buffer at pH 7.5. Under the optimized conditions, the whole cells regioselectively hydroxylated piceatannol, and the production of PHS reached 6.9 mM (1.8 g L-1) in 48h.

    Original languageEnglish
    Pages (from-to)193-198
    Number of pages6
    JournalBioscience, Biotechnology and Biochemistry
    Volume80
    Issue number1
    DOIs
    Publication statusPublished - 2016

    Keywords

    • HpaBC
    • Hydroxylation
    • Monooxygenase
    • Resveratrol
    • Stilbene

    ASJC Scopus subject areas

    • Biotechnology
    • Biochemistry
    • Molecular Biology
    • Applied Microbiology and Biotechnology
    • Analytical Chemistry
    • Organic Chemistry

    Fingerprint Dive into the research topics of 'Biocatalytic synthesis of 3,4,5,3',5'-pentahydroxy-trans-stilbene from piceatannol by two-component flavin-dependent monooxygenase HpaBC'. Together they form a unique fingerprint.

  • Cite this