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( P )/( M )-corinepalensin A, a pair of axially chiral prenylated bicoumarin enantiomers with a rare C-5 C-5 ′ linkage from the twigs of Coriaria nepalensis
Phytochemistry ( IF 3.8 ) Pub Date : 2018-05-01 , DOI: 10.1016/j.phytochem.2018.02.012
Lin Chen , Gui-Hua Tang , Fu-Liang Guo , Wei Li , Jun-Sheng Zhang , Bo Liu , Sheng Yin

A pair of undescribed bicoumarin enantiomers, (P)/(M)-corinepalensin A, two undescribed prenylated coumarins, corinepalensins B and C, along with ten known coumarins were isolated from the twigs of Coriaria nepalensis. (P)/(M)-corinepalensin A feature a rare C-5C-5' axially chiral linkage between two prenylated coumarin monomers. Their structures were determined by a combination of spectroscopic methods, single crystal X-ray diffraction, and ECD calculations. All isolates were evaluated for the inhibitory activity against phosphodiesterase-4 (PDE4), which is a drug target for the treatment of asthma and chronic obstructive pulmonary disease. Compounds (P)-corinepalensin A, (M)-corinepalensin A, corinepalensin B, norbraylin, braylin, and nepalin C exhibited significant inhibition with IC50 values ranging from 0.43 to 7.15 μM.

中文翻译:

( P )/( M )-corinepalensin A,一对轴向手性异戊二烯化双香豆素对映异构体,具有来自 Coriaria nepalensis 枝条的罕见 C-5 C-5 ' 键

一对未描述的双香豆素对映体 (P)/(M)-corinepalensin A、两种未描述的异戊二烯化香豆素、corinepalensins B 和 C,以及十种已知的香豆素从 Coriaria nepalensis 的枝条中分离出来。(P)/(M)-corinepalensin A 在两个异戊二烯化香豆素单体之间具有罕见的 C-5C-5' 轴向手性连接。它们的结构是通过光谱方法、单晶 X 射线衍射和 ECD 计算的组合确定的。评估了所有分离株对磷酸二酯酶 4 (PDE4) 的抑制活性,PDE4 是治疗哮喘和慢性阻塞性肺疾病的药物靶点。化合物 (P)-corinepalensin A、(M)-corinepalensin A、corinepalensin B、norbrayllin、braylin 和 nepalin C 表现出显着的抑制作用,IC50 值范围为 0.43 至 7.15 μM。
更新日期:2018-05-01
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