细胞毒性人参皂苷衍生物的分离、合成及结构
Isolation, synthesis and structures of cytotoxic ginsenoside derivatives.
作者信息
Lei Jun, Li Xiang, Gong Xiao-jie, Zheng Yi-nan
机构信息
College of Chinese Medicinal Materials, Jilin Agricultural University, Changchun 130118, P. R. China.
出版信息
Molecules. 2007 Sep 5;12(9):2140-50. doi: 10.3390/12092140.
Four known ginsenosides: ginsenoside-Rb1 (1), Rb3 (2), Rd (3) and Re (4) were isolated from the methanolic extract of the traditional Chinese medicine Panax ginseng C. A. Meyer. Further enzyme reactions and chemical modifications led us to obtain ginsenoside-M1 (5) and synthesize three novel mono-esters of ginsenoside-M1, ginsenoside-DM1 (6), PM1 (7) and SM1 (8) 30 - 50% of yield via a facile and green synthetic strategy. The structures were elucidated on the basis of extensive 1D- and 2DNMR, as well as high resolution ESI-TOF mass spectroscopic analyses. The isolated and synthetic compounds were tested in an anti-tumor bioassay, and compounds 5-8 showed considerable cytotoxicity (SRB) against several human cancer cell lines (breast cancer MCF-7, skin melanoma SK-MEL-2 and human ovarian carcinoma B16), but moderate effects on lung carcinoma COR-L23. The other ginsenosides showed no effects.
从传统中药人参（Panax ginseng C. A. Meyer）的甲醇提取物中分离出四种已知的人参皂苷：人参皂苷-Rb1（1）、Rb3（2）、Rd（3）和Re（4）。进一步的酶反应和化学修饰使我们获得了人参皂苷-M1（5），并通过简便且绿色的合成策略以30%-50%的产率合成了三种新型人参皂苷-M1单酯化物，即人参皂苷-DM1（6）、PM1（7）和SM1（8）。通过广泛的一维和二维核磁共振以及高分辨率电喷雾电离飞行时间质谱分析确定了其结构。对分离得到的化合物和合成化合物进行了抗肿瘤生物测定，化合物5-8对几种人类癌细胞系（乳腺癌MCF-7、皮肤黑色素瘤SK-MEL-2和人卵巢癌B16）表现出相当大的细胞毒性（SRB），但对肺癌COR-L23的作用中等。其他人参皂苷则没有效果。
Zotero 插件