Cycloartane and Oleanane Glycosides from the Tubers of Eranthis cilicica
Cycloartane and Oleanane Glycosides from the Tubers of Eranthis cilicica
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DOI：
10.3390/molecules24010069
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发表时间：
2019-01-01
期刊：
影响因子：
4.6
通讯作者：
Matsuo, Yukiko
中科院分区：
文献类型：
--
作者：
Watanabe, Kazuki;Mimaki, Yoshihiro;Matsuo, Yukiko
作为我们对毛茛科植物的连续研究的一部分，对Eranthiscilicica的块茎进行了植物化学分析，这导致分离出11个新的环阿屯烷糖苷（1-11）和一个新的齐墩果烷糖苷（13），以及一个已知的齐墩果烷糖苷（12）。新化合物的结构通过广泛的光谱分析确定，包括二维（2D）NMR和酶水解，然后通过X射线晶体学或色谱分析。化合物2的糖苷配基（1a）及其C-23差向异构体（8a）和齐墩果烷糖苷（12和13）对HL-60白血病细胞显示出细胞毒活性，IC 50值为10.6 M至101.6 M。HL-60细胞对8a（IC 50 14.8 M）比1a（IC 50 101.1 M）敏感得多，表明C-23构型与这些环Artane衍生物的细胞毒性相关。从用化合物12处理的HL-60细胞的形态学可以明显看出，化合物12部分诱导HL-60细胞的凋亡性细胞死亡。
Phytochemical analysis of the tubers of Eranthis cilicica was performed as part of our continuous study on the plants of the family Ranunculaceae, which resulted in the isolation of eleven new cycloartane glycosides (1-11) and one new oleanane glycoside (13), together with one known oleanane glycoside (12). The structures of the new compounds were determined by extensive spectroscopic analysis, including two-dimensional (2D) NMR, and enzymatic hydrolysis followed by either X-ray crystallographic or chromatographic analysis. The aglycone (1a) of 2 and its C-23 epimer (8a), and the oleanane glycosides (12 and 13) showed cytotoxic activity against HL-60 leukemia cells with IC50 values ranging from 10.6 M to 101.6 M. HL-60 cells were much more sensitive to 8a (IC50 14.8 M) than 1a (IC50 101.1 M), indicating that the C-23 configuration is associated with the cytotoxicity of these cycloartane derivatives. Compound 12 was revealed so as to partially induce apoptotic cell death in HL-60 cells, as was evident from morphology of HL-60 cells treated with 12.