(3β,6β,12β,23S,24R,25S)-16,23:23,26-diepoxy-6,12,24,25-tetrahydroxy-9,19-cycloart-3-O-β-D-xylopyranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (3β,6β,12β,23S,24R,25S)-16,23:23,26-diepoxy-6,12,24,25-tetrahydroxy-9,19-cycloart-3-O-β-D-xylopyranoside
• 英文别名: yunnanterpene F；(1R,3R,3'R,4R,4'S,5R,6R,8S,10S,12S,13S,14S,16R,18S,21R)-4,4',6,12,17,17-hexamethyl-18-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyspiro[9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosane-8,2'-oxolane]-3,3',4',14-tetrol
• 化学式: C₃₅H₅₆O₁₁
• 分子量: 652.823
• InChiKey: BURFZMFSWQCUCA-CHMXSDDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  46
• 可旋转键数：
  2
• 环数：
  8.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (3β,6β,12β,23S,24R,25S)-16,23:23,26-diepoxy-6,12,24,25-tetrahydroxy-9,19-cycloart-3-O-β-D-xylopyranoside 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 L-阿拉伯糖
  参考文献：
  名称：

  Triterpenes from the Aerial Parts of Cimicifuga yunnanensis and Their Antiproliferative Effects on p53^N236S Mouse Embryonic Fibroblasts

  摘要：

  Nine new triterpene derivatives, yunnanterpenes A-F (1-6), 15,16-seco-cimiterpenes A and B (7, 8), and cimilactone C (9), and 15 known analogues (10-24) were isolated from the aerial parts of Cimicifuga yunnanensis. The new structures were established using a combination of MS, NMR, and single-crystal X-ray diffraction techniques. WT MEFs (wildtype mouse embryonic fibroblasts) and tumorigenic cell lines p53(-/-)+H-RasV12 and ps3(-/-)+p53(N236S)+H-RasV12 were used for evaluating active structures, targeting p53(N236S) (corresponding to p53(N239S) in humans) mutation. Compound 5 showed nonselective activities against these cell lines, with IC50 values of 5.8, 8.6, and 6.0 mu M, respectively. Compound 4 exhibited greater selectivity against the p53(-/-)+p53(N236S)+H-RasV12 cells (IC50 5.5 mu M) than against the WT MEFs cells (IC50 14.3 mu M).

  DOI：

  10.1021/np4000262

文献信息

• Triterpenes from the Aerial Parts of <i>Cimicifuga yunnanensis</i> and Their Antiproliferative Effects on p53^N236S Mouse Embryonic Fibroblasts
  作者：Yin Nian、Hui Zhu、Wen-Ru Tang、Yin Luo、Jiang, Du、Ming-Hua Qiu

  DOI：10.1021/np4000262

  日期：2013.5.24

  Nine new triterpene derivatives, yunnanterpenes A-F (1-6), 15,16-seco-cimiterpenes A and B (7, 8), and cimilactone C (9), and 15 known analogues (10-24) were isolated from the aerial parts of Cimicifuga yunnanensis. The new structures were established using a combination of MS, NMR, and single-crystal X-ray diffraction techniques. WT MEFs (wildtype mouse embryonic fibroblasts) and tumorigenic cell lines p53(-/-)+H-RasV12 and ps3(-/-)+p53(N236S)+H-RasV12 were used for evaluating active structures, targeting p53(N236S) (corresponding to p53(N239S) in humans) mutation. Compound 5 showed nonselective activities against these cell lines, with IC50 values of 5.8, 8.6, and 6.0 mu M, respectively. Compound 4 exhibited greater selectivity against the p53(-/-)+p53(N236S)+H-RasV12 cells (IC50 5.5 mu M) than against the WT MEFs cells (IC50 14.3 mu M).