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Rare Thioglycosides from the Roots of Wasabia japonica

  • Chung Sub Kim
    Chung Sub Kim
    Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea
  • Joonseok Oh
    Joonseok Oh
    Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States
    Chemical Biology Institute, Yale University, West Haven, Connecticut 06516, United States
    More by Joonseok Oh
  • Lalita Subedi
    Lalita Subedi
    Gachon Institute of Pharmaceutical Science, Gachon University, Incheon 21936, Republic of Korea
    College of Pharmacy, Gachon University, #191, Hambakmoero, Yeonsu-gu, Incheon 21936, Republic of Korea
  • Sun Yeou Kim
    Sun Yeou Kim
    Gachon Institute of Pharmaceutical Science, Gachon University, Incheon 21936, Republic of Korea
    College of Pharmacy, Gachon University, #191, Hambakmoero, Yeonsu-gu, Incheon 21936, Republic of Korea
    More by Sun Yeou Kim
  • Sang Un Choi
    Sang Un Choi
    Korea Research Institute of Chemical Technology, Daejeon 34114, Republic of Korea
    More by Sang Un Choi
  • , and 
  • Kang Ro Lee*
    Kang Ro Lee
    Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea
    *Tel: +82-31-290-7710. Fax: +82-31-290-7730. E-mail: [email protected]
    More by Kang Ro Lee
Cite this: J. Nat. Prod. 2018, 81, 9, 2129–2133
Publication Date (Web):September 20, 2018
https://doi.org/10.1021/acs.jnatprod.8b00570
Copyright © 2018 American Chemical Society and American Society of Pharmacognosy

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    Abstract

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    Six new thioglycosides (16) were characterized from the roots of Wasabia japonica along with a known analogue (7). Of these compounds, 13 possess a disulfide bridge connecting the carbohydrate motif and the aglycone, which is extremely rare in Nature. In particular, compound 1 forms an unusual 1,4,5-oxadithiocane ring system. The structures of the isolated compounds were determined through conventional NMR and HRMS data analysis procedure, and computational methods with advanced statistics were used for the configurational assignments of 1 and two pairs of inseparable epimers, 2/3 and 4/5. All compounds were evaluated for their anti-inflammatory, neuroprotective, and cytotoxic activities, with 1 showing weak anti-inflammatory activity (IC50 41.2 μM).

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jnatprod.8b00570.

    • HRESIMS and 1D and 2D NMR spectra of 16 and computational data of 15 (PDF)

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