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Megastigmane Derivatives from the Cladodes of Opuntia humifusa and Their Nitric Oxide Inhibitory Activities in Macrophages.
Journal of Natural Products ( IF 5.1 ) Pub Date : 2020-03-02 , DOI: 10.1021/acs.jnatprod.9b01120
Mun Seok Jo 1 , Seoyoung Lee 2 , Jae Sik Yu 1 , Su Cheol Baek 1 , Young-Chang Cho 2 , Ki Hyun Kim 1
Affiliation  

Opuntia humifusa, known as the eastern prickly pear cactus and locally called "Cheonnyuncho" in Korea, is cultivated widely on Jeju Island, Korea. Phytochemical analysis of the methanolic extract of the cladodes of O. humifusa, for which previous research is relatively limited, was performed under the guidance of LC/MS-based analysis. As a result, one new megastigmane (1) and four new megastigmane glucosides (2-5) were isolated along with 18 known compounds (6-23). The structures of the new compounds were established by 1D and 2D NMR and HRESIMS, and their absolute configurations were established by chemical reactions, quantum chemical electronic circular dichroism calculations, and DP4+ analysis using the gauge-including atomic orbital NMR chemical shift calculations as well as the application of Snatzke's method. The isolated compounds (1-23) were tested for NO production inhibition in lipopolysaccharide (LPS)-induced RAW 264.7 cells to investigate their anti-inflammatory effects. Compounds 10 and 11 exhibited significant inhibitory effects on LPS-induced NO production in a dose-dependent manner. The potential mechanistic pathway of 10 and 11 was also investigated using Western blotting, indicating that compounds 10 and 11 inhibit NO through iNOS expression.

中文翻译:

来自仙人掌枝条的 Megastigmane 衍生物及其在巨噬细胞中的一氧化氮抑制活性。

Opuntia humifusa,被称为东方仙人掌,在韩国当地称为“Cheonnyuncho”,在韩国济州岛广泛种植。在基于 LC/MS 的分析的指导下,对 O. humifusa 枝条的甲醇提取物进行了植物化学分析,之前的研究相对有限。结果,与 18 种已知化合物 (6-23) 一起分离出了一种新的巨莨菪碱 (1) 和四种新的巨莨菪苷 (2-5)。新化合物的结构由一维和二维核磁共振和 HRESIMS 确定,它们的绝对构型通过化学反应、量子化学电子圆二色性计算和使用规范的 DP4+ 分析确定,包括原子轨道核磁共振化学位移计算以及Snatzke 方法的应用 在脂多糖 (LPS) 诱导的 RAW 264.7 细胞中测试分离的化合物 (1-23) 的 NO 产生抑制,以研究它们的抗炎作用。化合物 10 和 11 以剂量依赖的方式对 LPS 诱导的 NO 产生表现出显着的抑制作用。还使用蛋白质印迹研究了 10 和 11 的潜在机制途径,表明化合物 10 和 11 通过 iNOS 表达抑制 NO。
更新日期:2020-04-24
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