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A Novel Spermidine Macrocyclic Alkaloid from the Roots of Tripterygium wilfordii
Chemistry of Natural Compounds ( IF 0.8 ) Pub Date : 2020-05-01 , DOI: 10.1007/s10600-020-03070-7
Jianqun Liu , Qiushan Wu , Jicheng Shu , Rui Zhang , Lifang Liu

A novel 13-membered spermidine macrocyclic alkaloid, (2R)-9-furoyl-2-phenyl-1,5,9-triazacyclotridecane-4,13-dione, named celacarfurine (1), was isolated from the roots of Tripterygium wilfordii. Its structure has been elucidated on the basis of NMR and MS data. To the best of our knowledge, 13-membered spermidine macrocyclic alkaloids were rarely reported natural products; moreover, the known ones were generally in the 2S configuration and there was none or only one amide carbonyl in the macrocycle. A (2R)-13-membered spermidine macrocyclic alkaloid containing two amide carbonyls in the macrocycle (celacarfurine) is reported here for the first time. Compound 1 showed statistically significant inhibitory effects on IL-1β secretion in LPS-induced rat primary synovial fibroblasts at 10 μM.

中文翻译:

雷公藤根中一种新型亚精胺大环生物碱

一种新型 13 元亚精胺大环生物碱 (2R)-9-furoyl-2-phenyl-1,5,9-triazacyclotridecane-4,13-dione,名为 celacarfurine (1),是从雷公藤根中分离出来的。其结构已在核磁共振和质谱数据的基础上阐明。据我们所知,13 元亚精胺大环生物碱很少被报道为天然产物;此外,已知的一般为2S构型,大环中没有或只有一个酰胺羰基。在大环中含有两个酰胺羰基的 (2R)-13 元亚精胺大环生物碱 (celacarfurine) 是首次报道。化合物 1 在 10 μM 时对 LPS 诱导的大鼠原代滑膜成纤维细胞中的 IL-1β 分泌显示出统计学上显着的抑制作用。
更新日期:2020-05-01
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