Coumarin derivatives from the leaves and twigs of Murraya exotica L. and their anti-inflammatory activities,Phytochemistry

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Coumarin derivatives from the leaves and twigs of Murraya exotica L. and their anti-inflammatory activities
Phytochemistry ( IF 3.2 ) Pub Date : 2020-09-01 , DOI: 10.1016/j.phytochem.2020.112416
Haizhen Liang ₁ , Yuntao Shi ₁ , Kewu Zeng ₁ , Mingbo Zhao ₁ , Pengfei Tu ₁ , Yong Jiang ₁

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Fifteen previously undescribed coumarin derivatives, murratins A-M, including two pairs of coumarin enantiomers with a cyclopropane unit, two benzocoumarins, a dimeric coumarin, and eight C-8-substituted coumarins, together with six known analogues were isolated from the extract of the leaves and twigs of Murraya exotica L., a medicinal plant named "Jiulixiang" in Chinese. Their structures were elucidated on the basis of comprehensive analysis of 1D and 2D NMR and HRMS spectroscopic data, and the absolute configurations were assigned via comparison of the specific rotations, the ECD exciton coupling method, comparison of experimental and calculated ECD data, and the ECD data of in situ formed transition metal complexes. All the isolates were evaluated for their inhibitory effects on lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells, and five coumarin derivatives showed moderate inhibitory activities. The possible mechanism for NO inhibition of undescribed bioactive compounds was deduced to interact with iNOS protein via molecular docking. The above results shed some light on a better understanding of the traditional anti-inflammation effect of M. exotica and coumarins are disclosed to be its potential anti-inflammatory constituents.

中文翻译：

来自异国墨鱼叶和枝条的香豆素衍生物及其抗炎活性

从叶子的提取物中分离出 15 种以前未描述的香豆素衍生物 muratins AM，包括两对带有环丙烷单元的香豆素对映体、两种苯香豆素、一种二聚香豆素和八种 C-8 取代的香豆素，以及六种已知的类似物药用植物 Murraya extraa L. 的枝条，中文名为“九里香”。在综合分析一维和二维核磁共振和 HRMS 光谱数据的基础上阐明了它们的结构，并通过比旋光度的比较、ECD 激子耦合方法、实验和计算 ECD 数据的比较以及 ECD 确定了绝对构型。原位形成的过渡金属配合物的数据。评估了所有分离株对 RAW 264.7 细胞中脂多糖诱导的一氧化氮产生的抑制作用，五种香豆素衍生物显示出中等抑制活性。推测未描述的生物活性化合物的 NO 抑制的可能机制通过分子对接与 iNOS 蛋白相互作用。上述结果为更好地理解 M.extracia 的传统抗炎作用提供了一些启示，香豆素被公开为它的潜在抗炎成分。

更新日期：2020-09-01

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