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Absolute configuration-dependent epoxide formation from isoflavan-4-ol stereoisomers by biphenyl dioxygenase of Pseudomonas pseudoalcaligenes strain KF707

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Abstract

Biphenyl dioxygenase from Pseudomonas pseudoalcaligenes strain KF707 expressed in Escherichia coli was found to exhibit monooxygenase activity toward four stereoisomers of isoflavan-4-ol. LC–MS and LC–NMR analyses of the metabolites revealed that the corresponding epoxides formed between C2′ and C3′ on the B-ring of each isoflavan-4-ol substrate were the sole products. The relative reactivity of the stereoisomers was found to be in the order: (3S,4S)-cis-isoflavan-4-ol > (3R,4S)-trans-isoflavan-4-ol > (3S,4R)-trans-isoflavan-4-ol > (3R,4R)-cis-isoflavan-4-ol and this likely depended upon the absolute configuration of the 4-OH group on the isoflavanols, as explained by an enzyme–substrate docking study. The epoxides produced from isoflavan-4-ols by P. pseudoalcaligenes strain KF707 were further abiotically transformed into pterocarpan, the molecular structure of which is commonly found as part of plant-protective phytoalexins, such as maackiain from Cicer arietinum and medicarpin from Medicago sativa.

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Acknowledgement

This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MEST) (No. 2009-0083568).

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Author notes

  1. Jiyoung Seo

    Present address: Industrial Biotechnology and Bioenergy Research Center, Korea Research Institute of Bioscience and Biotechnology, Yuseong-gu, Daejeon, 305-806, South Korea

Authors and Affiliations

  1. School of Environmental Science and Engineering, Gwangju Institute of Science and Technology, Gwangju, 500-712, South Korea

    Jiyoung Seo, Ji-Young Ryu & Hor-Gil Hur

  2. International Environmental Research Center, Gwangju Institute of Science and Technology, Gwangju, 500-712, South Korea

    Su-Il Kang & Hor-Gil Hur

  3. Metalloenzyme Research Group and Department of Biotechnology, Chung-Ang University, Anseong, 456-756, South Korea

    Dongho Won, Mihyang Kim & Jaehong Han

  4. Natural Products Research Center, Korea Institute of Science and Technology—Gangneung Institute, Gangneung, 210-340, South Korea

    Suk-Woo Kang, Byung-Hun Um & Cheol-Ho Pan

  5. Department of Bioscience and Biotechnology, Konkuk University, Seoul, 143-701, South Korea

    Joong-Hoon Ahn & Youhoon Chong

  6. Department of Genome Systems, Yokohama City University, Kanazawa-ku, Yokohama, 236-0027, Japan

    Robert A. Kanaly

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  1. Jiyoung Seo
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Correspondence to Jaehong Han or Hor-Gil Hur.

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Seo, J., Kang, SI., Won, D. et al. Absolute configuration-dependent epoxide formation from isoflavan-4-ol stereoisomers by biphenyl dioxygenase of Pseudomonas pseudoalcaligenes strain KF707. Appl Microbiol Biotechnol 89, 1773–1782 (2011). https://doi.org/10.1007/s00253-010-2989-1

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  • DOI: https://doi.org/10.1007/s00253-010-2989-1

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