Anti-parasitic activity and computational studies on a novel labdane diterpene from the roots of Vachellia nilotica

IF 2.1 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Open Chemistry Pub Date : 2024-03-23 DOI:10.1515/chem-2024-0005

Naser F. Al-Tannak, John V. Anyam, Eman Y. Santali, Alexander I. Gray, Collins U. Ibeji, John O. Igoli

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Abstract

A new labdane diterpene characterized as 18α-O-trans-p-feruloyl-15-methyl-8(17)-labdanoate has been isolated from the roots of Vachellia nilotica. Also isolated were p-coumaric acid, ferulic acid, stearic acid, lupeol, and a mixture of β-sitosterol and stigmasterol. The compounds were obtained after a series of column chromatography on silica gel, and their structures were elucidated using NMR and LC-MS analyses. The new diterpene showed good anti-parasitic activity with an IC50 of 0.0177 µM against Trypanosoma brucei and 0.0154 µM against Leishmania major using an Alamar Blue assay. The compound also displayed very good inhibitory activity against Leishmania major compared to Trypanosoma brucei rhodesiense with a binding energy of −10.5 and −7.8 kcal/mol, respectively. Density functional theory analysis showed that the studied compound has low LUMO–HOMO energy, signifying a high chemical reactivity with the ability to donate electrons to electron-accepting species.

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关于尼罗河苣苔根中一种新型唇烷二萜的抗寄生虫活性和计算研究

从尼洛依木（Vachellia nilotica）的根中分离出了一种新的唇烷二萜，其特征为 18α-O- 反式对阿魏酰-15-甲基-8(17)-唇烷酸。此外，还分离出了对香豆酸、阿魏酸、硬脂酸、羽扇豆醇以及β-谷甾醇和豆甾醇的混合物。这些化合物在硅胶上经过一系列柱层析后得到，并通过核磁共振和液相色谱-质谱分析阐明了它们的结构。这种新的二萜化合物具有良好的抗寄生虫活性，在阿拉玛蓝检测法中，它对布氏锥虫的 IC50 值为 0.0177 µM，对大利什曼原虫的 IC50 值为 0.0154 µM。与布鲁氏锥虫相比，该化合物对大利什曼原虫也显示出非常好的抑制活性，其结合能分别为-10.5和-7.8 kcal/mol。密度泛函理论分析表明，所研究的化合物具有较低的 LUMO-HOMO 能量，这表明它具有较高的化学反应活性，能够向电子受体提供电子。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Open Chemistry CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

3.80

自引率

4.30%

发文量

审稿时长

6 weeks

期刊介绍： Open Chemistry is a peer-reviewed, open access journal that publishes original research, reviews and short communications in the fields of chemistry in an ongoing way. The central goal is to provide a hub for researchers working across all subjects to present their discoveries, and to be a forum for the discussion of the important issues in the field. The journal is the premier source for cutting edge research in fundamental chemistry and it provides high quality peer review services for its authors across the world. Moreover, it allows for libraries everywhere to avoid subscribing to multiple local publications, and to receive instead all the necessary chemistry research from a single source available to the entire scientific community.