Targeted isolation of cytotoxic germacranolide sesquiterpenes from Elephantopus scaber L. using small molecule accurate recognition technology
Targeted isolation of cytotoxic germacranolide sesquiterpenes from Elephantopus scaber L. using small molecule accurate recognition technology
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利用小分子精准识别技术从象草中靶向分离细胞毒性的吉马酸内酯倍半萜
DOI：
10.1016/j.bioorg.2020.104314
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发表时间：
2020
影响因子：
5.1
通讯作者：
Song Shao-Jiang
中科院分区：
文献类型：
--
作者：
Bai Ming;Zhang Yang-Yang;Dong Shu-Hui;Ren Hui;Chen Jing-Jie;Yao Guo-Dong;Liu Qing-Bo;Lin Bin;Huang Xiao-Xiao;Song Shao-Jiang
小分子准确识别技术(SMART)是一种用于快速预测粗提物和馏分中主要成分结构的新兴方法。在本研究中，通过SMART定向分离Elephantopus scabb提取物，得到了15个新的(1-15)和5个已知的Germacranolide倍半萜(16-20)。通过HRESIMS、核磁共振、X-射线单晶分析、改进的Mosher方法和量子化学计算的电子圆二色谱(ECD)对其结构进行了归属。结果表明，化合物14、16、18、19和20对肝癌细胞株具有明显的细胞毒作用，其中化合物14、16、18、19和20对肝癌细胞株(IC50，3.3~9.9μM)和肝癌细胞株(Hep3B，IC50，4.5~8.6μM)具有明显的细胞毒作用。进一步的研究表明，18可以通过线粒体功能障碍诱导肝癌细胞的凋亡。
Small molecule accurate recognition technology (SMART) is an emerging method for the rapid structural prediction of major constituents from crude extracts and fractions. In the present study, a targeted isolation of anElephantopus scaberextract by SMART resulted in the obtention of 15 new (1–15) and five known germacranolide sesquiterpenes (16–20). Their structures were assigned by extensively analyzing HRESIMS, NMR, X-ray crystallographic analyses, modified Mosher’s method results, and quantum chemical calculate electronic circular dichroism (ECD) spectra. All germacranolide sesquiterpenes were screened to determine their inhibitory effects with two hepatoma cell lines (HepG2 and Hep3B), and compounds14,16,18,19and20showed significant cytotoxic activities against the HepG2 (IC50, 3.3–9.9 μM) and Hep3B (IC50, 4.5–8.6 μM) cell lines. Further study suggested that18can induce the apoptosis of hepatoma cells via mitochondrial dysfunction.