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两种来自肉果秤锤树的新型2,3-断藿烷三萜衍生物及其抗增殖和抗菌活性。

Two new 2,3-seco-hopane triterpene derivatives from Megacodon stylophorus and their antiproliferative and antimicrobial activities.

作者信息

Liu Chao, Liao Zhi-Xin, Liu Shi-Jun, Ji Lan-Ju, Sun Hong-Fa

机构信息

Department of Pharmaceutical Engineering, School of Chemistry and Chemical Engineering, Southeast University, Nanjing, P. R. China.

Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining, P. R. China.

出版信息

Planta Med. 2014 Jul;80(11):936-41. doi: 10.1055/s-0034-1368612. Epub 2014 Jul 4.

DOI:10.1055/s-0034-1368612
PMID:24995501
Abstract

Chemical investigation of the ethanol extract of the whole plant of Megacodon stylophorus led to the isolation and identification of two new seco-hopane triterpenoids, 2,3-seco-22(29)-hopene-2-carboxyl-3-aldehyde (1) and 2,3-seco-4(23),22(29)-hopene-2-carboxyl-3-aldehyde (2), along with 10 known compounds, 3-12. All the isolates were reported from this plant for the first time. The structures of compounds 1 and 2 were determined by detailed analysis of their spectral data including 1D and 2D NMR. In addition, compound 1 was further analyzed by X-ray crystallography. Compounds 1-3 were evaluated for their in vitro anti-proliferative activities on HeLa, MCF-7, and Hep-G2 tumor cell lines. Compound 2 was active against the three cell lines with IC50 values of 3.6, 7.5, and 13.6 µM, respectively, while compound 1 exhibited cytotoxicity on MCF-7 (IC50 14.0 µM) and HeLa (IC50 18.2 µM) cell lines. Antimicrobial activities of compounds 1-2 (minimum inhibitory concentration values in the range of 3.12-12.50 mg/mL) were also observed.

摘要

对长柱大萼苣全草乙醇提取物进行化学研究,从中分离并鉴定出两种新的裂环何帕烷三萜类化合物,即2,3-裂环-22(29)-何帕烯-2-羧基-3-醛(1)和2,3-裂环-4(23),22(29)-何帕烯-2-羧基-3-醛(2),以及10种已知化合物(3 - 12)。所有分离物均首次从该植物中报道。化合物1和2的结构通过对其光谱数据(包括一维和二维核磁共振)的详细分析得以确定。此外,化合物1还通过X射线晶体学进行了进一步分析。对化合物1 - 3进行了体外对HeLa、MCF - 7和Hep - G2肿瘤细胞系的抗增殖活性评估。化合物2对这三种细胞系均有活性,IC50值分别为3.6、7.5和13.6 μM,而化合物1对MCF - 7(IC50 14.0 μM)和HeLa(IC50 18.2 μM)细胞系表现出细胞毒性。还观察到化合物1 - 2的抗菌活性(最低抑菌浓度值在3.12 - 12.5 mg/mL范围内)。

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