2. Academic Validation
  3. Rare Thioglycosides from the Roots of Wasabia japonica

Rare Thioglycosides from the Roots of Wasabia japonica

  • J Nat Prod. 2018 Sep 28;81(9):2129-2133. doi: 10.1021/acs.jnatprod.8b00570.
Chung Sub Kim 1,  Joonseok Oh 2 3,  Lalita Subedi 4 5,  Sun Yeou Kim 4 5,  Sang Un Choi 6,  Kang Ro Lee 1
Affiliations

Affiliations

  • 1 Natural Products Laboratory, School of Pharmacy , Sungkyunkwan University , Suwon 16419 , Republic of Korea.
  • 2 Department of Chemistry , Yale University , New Haven , Connecticut 06520 , United States.
  • 3 Chemical Biology Institute , Yale University , West Haven , Connecticut 06516 , United States.
  • 4 Gachon Institute of Pharmaceutical Science , Gachon University , Incheon 21936 , Republic of Korea.
  • 5 College of Pharmacy , Gachon University , #191, Hambakmoero , Yeonsu-gu , Incheon 21936 , Republic of Korea.
  • 6 Korea Research Institute of Chemical Technology , Daejeon 34114 , Republic of Korea.
PMID: 30232882 DOI: 10.1021/acs.jnatprod.8b00570
Abstract

Six new thioglycosides (1-6) were characterized from the roots of Wasabia japonica along with a known analogue (7). Of these compounds, 1-3 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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