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中国科学院昆明植物研究所知识管理系统
Knowledge Management System of Kunming Institute of Botany,CAS
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Funding Project:Chemical constituents and bioactivities research on Cimicifuga species have been became an international hotspot. There are abundant plant resources of this genus in China, however the step of exploitation is far fall behind the western world. In an attempt to fully utilize our domestic resources, our research group has been studying on the chemical constituents and their bioactivities, specially 9,19-cyclolanostanetriterpenes of this genus, since 2003. As a result, several cycloartane triterpenoids with potential anti-tumor activities were obtained for the first time in China. For further searching anti-tumor lead compounds with novel structures and more potent activities, in this thesis,the roots of C. yunnanensis and the aerial parts of C. foetida, which collected from Shangrila County in Yunnan Province, the roots of C. foetida, which collected from Heishitou Town in Guizhou Province and the roots of C. dahurica and C. heracleifolia, which collected from Qingyuan County in Liaoning Province were used as experimental materials and total 105 compounds were isolated and identified by different spectroscopic and chemical methods. Among these 105 compounds, there are 94 9,19-cyclolanostanetriterpenes,including 44 new constituents. All these new compounds can be categorized as Cimigenol-type, Shengmanol-type, Hydroxyshengmanol-type, Acteol-type, Dahurinol-type, Cimicidol-type, and 3,4-Seco-type, 15,16-Seco-type, which were very novel. The left 11 compounds are normal Chromones, sitosterols, oleanane triterpenes and a new Ergostane-type steoid. The isolated 9,19-cyclolanostane compounds were tested for their cytotoxicities against 15 human carcinoma cell lines, which included human hepatoma cell line HepG2, human breast carcinoma cell line MCF-7, human colorectal carcinoma cell line HT-19 and so on. 40 compounds showed activities and three of them, which isolated from C. yunnanensis exhibited as potent activities as positive control Taxol. Mechanism research indicated that these three compounds can increase the expression of p53 and bax, which led to the loss of mitochondrial potential and then resulted in the activation of caspase-7 and induced apoptosis of MCF-7. In addition, a series of compounds which isolated from the roots of C. foetida showed selective significant cytotoxicity (potent than positive controlcisplatin) against the human HepG2 cell line and a domestic patent was applied for these compounds. A conclusion of the structure-activity relationships of Cimigenol-type compounds were proposed: one of the key point for anti-tumor activities is at least one side of the compound has hydrophobic groups such as carbonyl, double bond substitute hydroxyl groups. At the end of this thesis, a comprehensive review about the distribution and utilization of the Cimicifuga genus worldwide, the structures of 9,19-cyclolanostanetriterpenes and their anti-climacteric syndrome, anti-osteoporotic and anti-tumor activities were gave