Phytochemistry ( IF 3.2 ) Pub Date : 2023-09-12 , DOI: 10.1016/j.phytochem.2023.113859 Zhao-Chun Zhan 1 , Yi-Ping Xia 1 , Qing Tang 1 , Hui-Hui Zhu 1 , Jing-Yi Du 1 , Jun-Xing Cai 1 , Yan-Jun Chen 2 , Zhong-Nan Wu 1 , Yao-Lan Li 1 , Neng-Hua Chen 3 , Guo-Cai Wang 1 , Yu-Bo Zhang 2
Fifteen undescribed lindenane-type sesquiterpenoid dimers, designated chloranholides F−T (1−15), together with twenty-five known analogs (16−40), were isolated from the whole plants of Chloranthus holostegius. The isolate structures were elucidated by analysis of spectroscopic data and chemical methods, and their absolute configurations were determined by X-ray crystallography and electronic circular dichroism spectra. In anti-neuroinflammatory assays, all isolates were evaluated by examination of their inhibitory effect on nitric oxide (NO) in LPS-stimulated BV-2 cells, and the results showed that 21−24, 26, 30, 32 and 36 significantly inhibited the production of the inflammatory mediator NO, with IC50 values ranging from 3.18 to 11.46 μM, which was better than that of quercetin. Structure-activity relationship analysis revealed that two essential functional groups played an indispensable role in the anti-inflammatory effects. Moreover, 22 and 24 inhibited the LPS-induced upregulation of iNOS and COX-2 enzymes in BV-2 microglia at the protein level.
中文翻译:
来自金粟兰的林烯倍半萜二聚体在 BV-2 小胶质细胞中具有抗神经炎症活性
从金粟兰(Chloranthus holostegius)的整株植物中分离出15 种未描述的茚烷型倍半萜二聚体,命名为金雀花素 F−T ( 1 − 15 ),以及 25 种已知类似物 ( 16 − 40 ) 。通过光谱数据分析和化学方法阐明了分离物的结构,并通过X射线晶体学和电子圆二色光谱确定了它们的绝对构型。在抗神经炎症测定中,通过检查其对 LPS 刺激的 BV-2 细胞中一氧化氮 (NO) 的抑制作用来评估所有分离株,结果表明21 – 24、26、30、32和36显着抑制炎症介质NO的产生,IC 50值范围为3.18至11.46 μM,优于槲皮素。构效关系分析表明,两个重要的官能团在抗炎作用中发挥着不可或缺的作用。此外,22和24在蛋白质水平上抑制BV-2小胶质细胞中LPS诱导的iNOS和COX-2酶的上调。