28-O-α-L-rhamnopyranosylbetulin 3β-O-α-L-rhamnopyranoside | 1104464-26-7

• 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: 28-O-α-L-rhamnopyranosylbetulin 3β-O-α-L-rhamnopyranoside
• 英文别名: betulin 3-O-,28-O-bis(α-L-rhamnopyranoside)；28-O-α-L-rhamnopyranosylbetulin 33-O-α-L-rhamnopyranoside；(2R,3R,4R,5R,6S)-2-[[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-9-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-3a-yl]methoxy]-6-methyloxane-3,4,5-triol
• CAS: 1104464-26-7
• 化学式: C₄₂H₇₀O₁₀
• 分子量: 735.012
• InChiKey: KGKUKFARCFUSCY-JUBDGWICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  52
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  28-O-2",3",4"-tri-O-benzoyl-α-L-rhamnopyranosylbetulin 3β-O-2',3',4'-tri-O-benzoyl-α-L-rhamnopyranoside 在 sodium hydroxide 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以53 mg的产率得到28-O-α-L-rhamnopyranosylbetulin 3β-O-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis and Cytotoxicity of Bidesmosidic Betulin and Betulinic Acid Saponins

  摘要：

  The naturally occurring cytotoxic saponin 28-O-beta-D-glucopyranosylbetulinic acid 3 beta-O-alpha-L-arabinopyranoside (3) was easily synthesized along with seven bidesmosidic saponins starting from the lupane-type triterpenoids betulin (1) and betulinic acid (2). As highlighted by the preliminary cytotoxicity evaluation against A549, DLD-1, MCF7, and PC-3 human cancer cell lines, the bidesmosidic betulin saponin 22a, bearing alpha-L-rhamnopyranoside moieties at both C-3 and C-28 positions, was determined to be a potent cytotoxic agent (IC50 1.8-1.9 mu M).

  DOI：

  10.1021/np800579x