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新疆阿魏地上部分中未描述的倍半萜香豆素及其在脂多糖刺激的RAW 264.7巨噬细胞中的抗炎活性

Undescribed sesquiterpene coumarins from the aerial parts of Ferula sinkiangensis and their anti-inflammatory activities in lipopolysaccharide-stimulated RAW 264.7 macrophages.

作者信息

Wang Junchi, Huo Xiaoshuang, Wang Huaxiang, Dong Aijun, Zheng Qi, Si Jianyong

机构信息

The Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing, 100193, PR China.

The Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing, 100193, PR China.

出版信息

Phytochemistry. 2023 Jun;210:113664. doi: 10.1016/j.phytochem.2023.113664. Epub 2023 Mar 27.

Abstract

Eight undescribed sesquiterpene coumarins (1-8) and twenty known ones (9-28), were isolated from the aerial parts of Ferula sinkiangensis K. M. Shen. Their structures were elucidated based on the comprehensive analysis of UV, IR, HRESIMS, 1D, and 2D NMR data. The absolute configuration of 1 was determined by single crystal X-Ray diffraction, while the absolute configurations of 2-8 were determined by comparisons of experimental and calculated electrostatic circular dichroism spectra. Compound 2 is the first hydroperoxy sesquiterpene coumarin from the genus Ferula, while compound 8 has an unusual 5',8'-peroxo bridge. Griess reaction results indicated compound 18 significantly decreased nitric oxide production of the lipopolysaccharide-stimulated RAW 264.7 macrophages with an IC value of 2.3 μM, and ELISA results revealed that compound 18 effectively inhibited tumor necrosis factor-α, interleukin (IL)-1β, and IL-6 expressions.

摘要

从新疆阿魏(Ferula sinkiangensis K. M. Shen)地上部分分离得到8个未报道的倍半萜香豆素(1 - 8)和20个已知化合物(9 - 28)。通过对紫外光谱(UV)、红外光谱(IR)、高分辨电喷雾电离质谱(HRESIMS)、一维核磁共振(1D NMR)和二维核磁共振(2D NMR)数据的综合分析确定了它们的结构。化合物1的绝对构型通过单晶X射线衍射确定,而化合物2 - 8的绝对构型通过实验和计算的静电圆二色光谱比较确定。化合物2是阿魏属中首个含有氢过氧基的倍半萜香豆素,而化合物8具有不寻常的5',8'-过氧桥。格里斯反应结果表明,化合物18显著降低脂多糖刺激的RAW 264.7巨噬细胞中一氧化氮的产生,半数抑制浓度(IC)值为2.3 μM,酶联免疫吸附测定(ELISA)结果显示,化合物18有效抑制肿瘤坏死因子-α、白细胞介素(IL)-1β和IL-6的表达。

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