(3β,17R,23R,24S)-15,16-seco-14-formyl-16-oxo-16,23-epoxy-9,19-cycloart-3-O-α-L-arabinopyranoside | 1431527-26-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3β,17R,23R,24S)-15,16-seco-14-formyl-16-oxo-16,23-epoxy-9,19-cycloart-3-O-α-L-arabinopyranoside
• 英文别名: 15,16-seco-cimiterpene A；(1R,3S,6R,7S,8R,11R,13S)-6-[(3R,4R,6R)-6-[(1S)-1,2-dihydroxy-2-methylpropyl]-4-methyl-2-oxooxan-3-yl]-6,7,12,12-tetramethyl-13-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxytetracyclo[9.4.0.01,3.03,8]pentadecane-7-carbaldehyde
• CAS: 1431527-26-2
• 化学式: C₃₅H₅₆O₁₀
• 分子量: 636.824
• InChiKey: SQOTWNXPLYHYQJ-GNPZSCJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  45
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  163
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (3β,17R,23R,24S)-15,16-seco-14-formyl-16-oxo-16,23-epoxy-9,19-cycloart-3-O-α-L-arabinopyranoside 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