b-D-吡喃葡萄糖苷,(3a,7a,17a,20S,23R,24S)-3-(乙酰氧基)-23,24,25-三羟基-13,30-环达玛烷-7-基,6-乙酸酯(9CI) | 144608-17-3

• 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
• 中文名称: b-D-吡喃葡萄糖苷,(3a,7a,17a,20S,23R,24S)-3-(乙酰氧基)-23,24,25-三羟基-13,30-环达玛烷-7-基,6-乙酸酯(9CI)
• 英文名称: cumingianoside A
• 英文别名: [(2R,3S,4S,5R,6R)-6-[[(1S,2R,3R,5R,7R,10S,11R,14R,15S)-7-acetyloxy-2,6,6,10-tetramethyl-15-[(2R)-4,5,6-trihydroxy-6-methylheptan-2-yl]-3-pentacyclo[12.3.1.01,14.02,11.05,10]octadecanyl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• CAS: 144608-17-3
• 化学式: C₄₀H₆₆O₁₂
• 分子量: 738.957
• InChiKey: LWBFDADHSVYUPS-RFCUTSAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  52
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  192
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  b-D-吡喃葡萄糖苷,(3a,7a,17a,20S,23R,24S)-3-(乙酰氧基)-23,24,25-三羟基-13,30-环达玛烷-7-基,6-乙酸酯(9CI) 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以46 mg的产率得到b-D-Glucopyranoside, (3a,7a,17a,20S,23R,24S)-3-(acetyloxy)-23,24,25-trihydroxy-13,30-cyclodammaran-7-yl(9CI)
  参考文献：
  名称：

  Anti-tumor agents. 136. Cumingianosides A-F, potent antileukemic new triterpene glucosides, and cumindysosides A and B, trisnor- and tetranortriterpene glucosides with a 14,18-cycloapoeuphane-type skeleton from Dysoxylum cumingianum

  摘要：

  Six new triterpene glucosides, cumingianosides A-F (1-6) as well as a trisnor- and a tetranortriterpene glucoside, cumindysosides A (7) and B (8), respectively, with a 14,18-cycloapoeuphane-type skeleton have been isolated from Dysoxylum cumingianum as antileukemic principles. The structures were established on the basis of chemical and spectroscopic evidence. Among them, compounds 1 and 3 exhibited potent selective cytotoxicity against MOLT-4 human leukemia cell with ED50 of <0.006 25 and <0.0045 mug/mL, respectively.

  DOI：

  10.1021/jo00051a050