Isolation, Absolute Configuration, and Biological Activities of Chebulic Acid and Brevifolincarboxylic Acid Derivatives from Euphorbia hirta.,Journal of Natural Products

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Isolation, Absolute Configuration, and Biological Activities of Chebulic Acid and Brevifolincarboxylic Acid Derivatives from Euphorbia hirta.
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-03-06 , DOI: 10.1021/acs.jnatprod.9b00877
Zi-Ni Yang ₁ , Bao-Jun Su ₁ , Ya-Qi Wang ₁ , Hai-Bing Liao ₁ , Zhen-Feng Chen ₁ , Dong Liang ₁

Affiliation

Twenty new chebulic acid and brevifolincarboxylic acid derivatives, including eight optically pure or achiral compounds (1-7 and 14) and six pairs of enantiomers (8a/8b-13a/13b), along with nine known analogues (15-23), were isolated from an EtOH extract of the aerial parts of Euphorbia hirta. The absolute configurations of the new compounds were assigned based on single-crystal X-ray diffraction analysis and comparison of the experimental and calculated ECD data. Racemic or scalemic mixtures of 8-13 were isolated, and their enantiomers were analyzed by chiral-phase HPLC-ECD measurements. Compound 12 possesses an unprecedented 2H-cyclopenta[de]chromene-2,5(4H)-dione scaffold. Compounds 12, 20, and 23 displayed moderate inhibitory effects against lipopolysaccharide-induced nitric oxide production in BV-2 microglial cells, while all the isolates exhibited significant DPPH radical scavenging activities with EC50 values of 2.2-15.8 μM.

中文翻译：

大戟酸和短叶酸衍生物的分离、绝对构型和生物活性。

20 种新的 chebulic 酸和短叶黄素羧酸衍生物，包括 8 种光学纯或非手性化合物（1-7 和 14）和 6 对对映异构体（8a/8b-13a/13b），以及 9 种已知类似物（15-23），从 Euphorbia hirta 地上部分的乙醇提取物中分离。基于单晶 X 射线衍射分析以及实验和计算 ECD 数据的比较，确定了新化合物的绝对构型。分离出 8-13 的外消旋或缩放混合物，并通过手性相 HPLC-ECD 测量分析它们的对映异构体。化合物 12 拥有前所未有的 2H-cyclopenta[de]chromene-2,5(4H)-dione 支架。化合物 12、20 和 23 对 BV-2 小胶质细胞中脂多糖诱导的一氧化氮产生具有中等抑制作用，

更新日期：2020-03-06

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