28-O-acetylbetulin-3-yl-β-D-glucopyranoside | 267219-65-8

• 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-acetylbetulin-3-yl-β-D-glucopyranoside
• 英文别名: 28-O-acetyl-3β-O-(β-D-glucopyranosyl)-lup-20(29)-ene；[(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,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl acetate
• CAS: 267219-65-8
• 化学式: C₃₈H₆₂O₈
• 分子量: 646.905
• InChiKey: WENSCPLYCPJIKC-SOILWKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  46
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  28-acetoxybetulin 在 水 、 mercury(II) cyanide 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 52.0h， 生成 28-O-acetylbetulin-3-yl-β-D-glucopyranoside
  参考文献：
  名称：

  In vitro anticancer studies of α- and β-d-glucopyranose betulin anomers

  摘要：

  Four derivatives of betulin containing a D-glucopyranosyl moiety at C3 position were synthesized and characterized by H-1 and C-13 NMR spectroscopy as well as mass spectrometry. The crystal structure of 28-O-acetylbetulin-3-yl-beta-D-(2',3',4',6'-tetra-O-acetyl)glucopyranoside was determined. The compounds were tested against fifteen tumor cell lines of different histogenic origins. The alpha- and beta-anomers of 28-O-acetylbetulin-3-yl-D-glucopyranoside, exerted a dose dependent antiproliferative action towards the tumor cell lines. Treatment of HCT-116 cells for 24 h induced apoptosis, which was confirmed by the appearance of a typical ladder pattern in the DNA fragmentation assay and cell cycle analysis. The alpha- and beta-anomers of 28-O-acetylbetulin-3-yl-D-glucopyranoside seem to induce apoptosis by activation of different upstream caspases on colon cancer HCT-116 cell line. (C) 2010 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.cbi.2010.02.038