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Rare Thioglycosides from the Roots of Wasabia japonica.
Journal of Natural Products ( IF 5.1 ) Pub Date : 2018-09-20 , 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
Affiliation  

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).

中文翻译:

山葵根中的稀有硫糖苷。

从山葵的根中鉴定出六个新的硫代糖苷(1-6)以及已知的类似物(7)。在这些化合物中,1-3具有连接碳水化合物基序和糖苷配基的二硫键,这在自然界中极为罕见。特别地,化合物1形成不寻常的1,4,5-恶二硫烷环系统。通过常规的NMR和HRMS数据分析程序确定分离出的化合物的结构,并使用具有高级统计数据的计算方法对1和2对不可分离的差向异构体2/3和4/5进行构型分配。对所有化合物的抗炎,神经保护和细胞毒性活性进行了评估,其中1种抗炎活性较弱(IC50 41.2μM)。
更新日期:2018-09-20
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