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

IF 3.8 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Frontiers in Chemistry Pub Date : 2022-04-29 DOI:10.3389/fchem.2022.885487

Huijuan Wang, Guoxu Ma, Huaxiang Wang, Lingyu Li, A. Dong, Huiping Liu, Xiao-Yang Huo, J. Si, Junchi Wang

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引用次数: 0

Abstract

Four novel triterpenoid alkaloids, siragrosvenins A–D (1–4), and two new cucurbitane-type triterpenoids, siragrosvenins E–F (5, 6), together with eight known analogs (7−14), were isolated from the roots of Siraitia grosvenorii. Compounds 1−4 possessed a rare cucurbitane-type triterpenoid scaffold, featuring an extra pyrazine unit via the Strecker reaction in the cucurbitane framework. Compound 5 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 1–4. In vitro cytotoxicity screening found that compounds 4, 8, 9, 13, and 14 exhibited remarkable cytotoxic activities against three cell lines with IC50 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 via the induction of G2/M phase arrest and significantly induced apoptosis in MCF-7 cells.

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罗汉果根中具有潜在细胞毒性的新型三萜生物碱

从罗汉果(Siraitia grosvenorii)的根中分离到了4个新的三萜生物碱siragrosvenins A-D(1-4)和2个新的葫芦烷型三萜siragrosvenins E-F(5,6)以及8个已知的类似物(7−14)。化合物1 ~ 4具有罕见的葫芦烷型三萜支架，在葫芦烷框架中通过streker反应增加了一个吡嗪单元。化合物5为6/6/6/5/6 -熔融多环体系，侧链上有一个罕见的呋喃和吡喃环。所有的结构都通过广泛的光谱分析进行了表征，包括hresms, NMR和x射线晶体学数据。值得注意的是，首次采用DP4+分析方法确定了化合物1-4侧链上三羟基丁基部分的绝对构型。体外细胞毒筛选发现，化合物4、8、9、13和14对3种细胞系具有显著的细胞毒活性，IC50值在1.44 ~ 9.99 μM之间。Siragrosvenin D对MCF-7细胞具有显著的细胞毒活性。结果表明，其通过诱导G2/M期阻滞抑制MCF-7细胞增殖，降低MCF-7细胞活力，并显著诱导MCF-7细胞凋亡。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Frontiers in Chemistry Chemistry-General Chemistry

CiteScore

8.50

自引率

3.60%

发文量

1540

审稿时长

12 weeks

期刊介绍： Frontiers in Chemistry is a high visiblity and quality journal, publishing rigorously peer-reviewed research across the chemical sciences. Field Chief Editor Steve Suib at the University of Connecticut is supported by an outstanding Editorial Board of international researchers. This multidisciplinary open-access journal is at the forefront of disseminating and communicating scientific knowledge and impactful discoveries to academics, industry leaders and the public worldwide. Chemistry is a branch of science that is linked to all other main fields of research. The omnipresence of Chemistry is apparent in our everyday lives from the electronic devices that we all use to communicate, to foods we eat, to our health and well-being, to the different forms of energy that we use. While there are many subtopics and specialties of Chemistry, the fundamental link in all these areas is how atoms, ions, and molecules come together and come apart in what some have come to call the “dance of life”. All specialty sections of Frontiers in Chemistry are open-access with the goal of publishing outstanding research publications, review articles, commentaries, and ideas about various aspects of Chemistry. The past forms of publication often have specific subdisciplines, most commonly of analytical, inorganic, organic and physical chemistries, but these days those lines and boxes are quite blurry and the silos of those disciplines appear to be eroding. Chemistry is important to both fundamental and applied areas of research and manufacturing, and indeed the outlines of academic versus industrial research are also often artificial. Collaborative research across all specialty areas of Chemistry is highly encouraged and supported as we move forward. These are exciting times and the field of Chemistry is an important and significant contributor to our collective knowledge.