Efficient monooxygenase-catalyzed piceatannol production

Application of cyclodextrins for reducing product inhibition

Toshiki Furuya, Masahiko Sai, Kuniki Kino

    Research output: Contribution to journalArticle

    3 Citations (Scopus)

    Abstract

    Piceatannol is a rare, costly plant-based stilbene derivative and exhibits various health-enhancing properties. Recently, we demonstrated that piceatannol could be produced from resveratrol through site-selective hydroxylation using Escherichia coli cells expressing the monooxygenase HpaBC. However, piceatannol production ceased at approximately 25 mM, even when sufficient levels of the substrate resveratrol remained in the reaction mixture. In this study, we found that high concentrations (>20–25 mM) of piceatannol significantly inhibited the HpaBC-catalyzed reaction. Cyclodextrins (CDs) reportedly encapsulate various hydrophobic compounds. We found that the addition of β-CD or γ-CD to the reaction mixture reduced the inhibition caused by the product piceatannol. The effects of β-CD on piceatannol production were more pronounced than those of γ-CD at high concentrations of the substrate resveratrol and CDs. The production of piceatannol reached 49 mM (12 g L−1) in the presence of β-CD, a level twice that achieved in the absence of β-CD. The technique described here might be applicable to the bioproduction of other stilbenes and structurally related compounds.

    Original languageEnglish
    JournalJournal of Bioscience and Bioengineering
    DOIs
    Publication statusAccepted/In press - 2018 Jan 1

    Fingerprint

    Cyclodextrins
    Mixed Function Oxygenases
    Resveratrol
    Stilbenes
    Hydroxylation
    3,3',4,5'-tetrahydroxystilbene
    Substrates
    Escherichia coli
    Cells
    Health
    Derivatives

    Keywords

    • Cyclodextrin
    • Monooxygenase
    • Piceatannol
    • Product inhibition
    • Resveratrol
    • Whole-cell catalyst

    ASJC Scopus subject areas

    • Biotechnology
    • Bioengineering
    • Applied Microbiology and Biotechnology

    Cite this

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    title = "Efficient monooxygenase-catalyzed piceatannol production: Application of cyclodextrins for reducing product inhibition",
    abstract = "Piceatannol is a rare, costly plant-based stilbene derivative and exhibits various health-enhancing properties. Recently, we demonstrated that piceatannol could be produced from resveratrol through site-selective hydroxylation using Escherichia coli cells expressing the monooxygenase HpaBC. However, piceatannol production ceased at approximately 25 mM, even when sufficient levels of the substrate resveratrol remained in the reaction mixture. In this study, we found that high concentrations (>20–25 mM) of piceatannol significantly inhibited the HpaBC-catalyzed reaction. Cyclodextrins (CDs) reportedly encapsulate various hydrophobic compounds. We found that the addition of β-CD or γ-CD to the reaction mixture reduced the inhibition caused by the product piceatannol. The effects of β-CD on piceatannol production were more pronounced than those of γ-CD at high concentrations of the substrate resveratrol and CDs. The production of piceatannol reached 49 mM (12 g L−1) in the presence of β-CD, a level twice that achieved in the absence of β-CD. The technique described here might be applicable to the bioproduction of other stilbenes and structurally related compounds.",
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    AU - Furuya, Toshiki

    AU - Sai, Masahiko

    AU - Kino, Kuniki

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    N2 - Piceatannol is a rare, costly plant-based stilbene derivative and exhibits various health-enhancing properties. Recently, we demonstrated that piceatannol could be produced from resveratrol through site-selective hydroxylation using Escherichia coli cells expressing the monooxygenase HpaBC. However, piceatannol production ceased at approximately 25 mM, even when sufficient levels of the substrate resveratrol remained in the reaction mixture. In this study, we found that high concentrations (>20–25 mM) of piceatannol significantly inhibited the HpaBC-catalyzed reaction. Cyclodextrins (CDs) reportedly encapsulate various hydrophobic compounds. We found that the addition of β-CD or γ-CD to the reaction mixture reduced the inhibition caused by the product piceatannol. The effects of β-CD on piceatannol production were more pronounced than those of γ-CD at high concentrations of the substrate resveratrol and CDs. The production of piceatannol reached 49 mM (12 g L−1) in the presence of β-CD, a level twice that achieved in the absence of β-CD. The technique described here might be applicable to the bioproduction of other stilbenes and structurally related compounds.

    AB - Piceatannol is a rare, costly plant-based stilbene derivative and exhibits various health-enhancing properties. Recently, we demonstrated that piceatannol could be produced from resveratrol through site-selective hydroxylation using Escherichia coli cells expressing the monooxygenase HpaBC. However, piceatannol production ceased at approximately 25 mM, even when sufficient levels of the substrate resveratrol remained in the reaction mixture. In this study, we found that high concentrations (>20–25 mM) of piceatannol significantly inhibited the HpaBC-catalyzed reaction. Cyclodextrins (CDs) reportedly encapsulate various hydrophobic compounds. We found that the addition of β-CD or γ-CD to the reaction mixture reduced the inhibition caused by the product piceatannol. The effects of β-CD on piceatannol production were more pronounced than those of γ-CD at high concentrations of the substrate resveratrol and CDs. The production of piceatannol reached 49 mM (12 g L−1) in the presence of β-CD, a level twice that achieved in the absence of β-CD. The technique described here might be applicable to the bioproduction of other stilbenes and structurally related compounds.

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