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来自……根部的具有潜在细胞毒性活性的新型三萜生物碱

Novel Triterpenoid Alkaloids With Their Potential Cytotoxic Activity From the Roots of .

作者信息

Wang Huijuan, Ma Guoxu, Wang Huaxiang, Li Lingyu, Dong Aijun, Liu Huiping, Huo Xiaoshuang, Si Jianyong, Wang Junchi

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 and Peking Union Medical College, Beijing, China.

出版信息

Front Chem. 2022 Apr 29;10:885487. doi: 10.3389/fchem.2022.885487. eCollection 2022.

Abstract

Four novel triterpenoid alkaloids, siragrosvenins A-D (), and two new cucurbitane-type triterpenoids, siragrosvenins E-F (, ), together with eight known analogs (), were isolated from the roots of . Compounds possessed a rare cucurbitane-type triterpenoid scaffold, featuring an extra pyrazine unit the Strecker reaction in the cucurbitane framework. Compound displayed a 6/6/6/5/6/5-fused polycyclic ring system, with an uncommon fused furan and pyran ring in the side chain. All the structures were characterized by extensive spectroscopic analysis, including HRESIMS, NMR, and X-ray crystallographic data. It is worth noting that the DP4 analysis method was applied for the first time to determine the absolute configurations of the trihydroxybutyl moiety in the side chain of compounds . cytotoxicity screening found that compounds and exhibited remarkable cytotoxic activities against three cell lines with IC values ranging from 1.44 to 9.99 μM. Siragrosvenin D shows remarkable cytotoxic activity on MCF-7 cells. As a result, it inhibited the proliferation of MCF-7 cells and reduced their viability the induction of G2/M phase arrest and significantly induced apoptosis in MCF-7 cells.

摘要

从[植物名称]的根部分离出了四种新型三萜生物碱,西拉格罗斯文宁A - D([具体结构简式]),以及两种新的葫芦烷型三萜,西拉格罗斯文宁E - F([具体结构简式]),还有八个已知类似物([具体结构简式])。化合物[具体化合物编号]具有罕见的葫芦烷型三萜骨架,其在葫芦烷骨架中通过斯特雷克反应具有一个额外的吡嗪单元。化合物[具体化合物编号]展示了一个6/6/6/5/6/5稠合的多环体系,在侧链中有一个不常见的稠合呋喃环和吡喃环。所有结构均通过广泛的光谱分析进行表征,包括高分辨电喷雾电离质谱(HRESIMS)、核磁共振(NMR)和X射线晶体学数据。值得注意的是,首次应用DP4分析方法来确定化合物[具体化合物编号]侧链中三羟基丁基部分的绝对构型。细胞毒性筛选发现,化合物[具体化合物编号]和[具体化合物编号]对三种细胞系表现出显著的细胞毒性活性,IC值范围为1.44至9.99 μM。西拉格罗斯文宁D对MCF - 7细胞显示出显著的细胞毒性活性。结果,它抑制了MCF - 7细胞的增殖并降低了它们的活力,诱导了G2/M期阻滞并显著诱导了MCF - 7细胞凋亡。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0653/9099095/a38770a2314a/fchem-10-885487-g001.jpg

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