lupeol 3-O-β-D-glucopyranoside | 78657-52-0

• 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: lupeol 3-O-β-D-glucopyranoside
• 英文别名: 3β-O-(β-D-glucopyranosyl)-lup-20(29)-ene
• CAS: 78657-52-0
• 化学式: C₃₆H₆₀O₆
• 分子量: 588.869
• InChiKey: HBVSMCMQYQJBEV-JQMDXBRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 重原子数：
  42.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  99.38
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  lupeol 3-O-β-D-glucopyranoside 、 碘甲烷 在 盐酸 、 溶剂黄146 、 silver(l) oxide 作用下， 生成 2,3,4,6-tetra-O-methyl-D-glucopyranose
  参考文献：
  名称：

  一种来自刺叶树根的三萜皂苷

  摘要：

  摘要 从鼠尾草乙醇提取物中分离得到一种新的三萜皂苷。它被证明是 [α-l -arabinofuranosyl-(1 → 4)-β-d -glucuronopyranosyl(1 → 3)]-3β-hydroxy-lup-20 (29)-ene。

  DOI：

  10.1016/0031-9422(81)85232-6
• 作为产物：
  描述：

  在 甲醇 、 sodium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 lupeol 3-O-β-D-glucopyranoside
  参考文献：
  名称：

  TRITERPENES DERIVATIVES AND USES THEREOF AS ANTITUMOR AGENTS OR ANTI-INFLAMMATORY AGENTS

  摘要：

  式（1）的化合物：其中R1选自H、α-L-葡萄糖苷、α-D-甘露糖苷、β-D-木糖苷、β-D-葡萄糖苷和α-D-阿拉伯糖苷组成的群；R2选自CH3、COOH、CH2OH、COOCH3和CH2O-α-D-阿拉伯糖苷；但化合物的式（I）不是式（I）中R1为β-D-葡萄糖苷且R2为COOH的化合物；其中R1为α-L-葡萄糖苷且R2为CH3；其中R1为β-D-葡萄糖苷且R2为CH2OH；其中R1为β-D-木糖苷且R2为CH2OH；其中R1为α-L-葡萄糖苷且R2为COOCH3；其中R1为H且R2为CH3；其中R1为H且R2为CH2OH；其中R1为H且R2为COOH；或其中R1为H且R2为COOCH3，或其药学上可接受的盐。

  公开号：

  US20080167254A1

文献信息

• Glycosidation of lupane-type triterpenoids as potent in vitro cytotoxic agents
  作者：Charles Gauthier、Jean Legault、Maxime Lebrun、Philippe Dufour、André Pichette

  DOI：10.1016/j.bmc.2006.05.075

  日期：2006.10

  The weak hydrosolubility of betulinic acid (3) hampers the clinical development of this natural anticancer agent. In order to circumvent this problem and to enhance the pharmacological properties of betulinic acid (3) and the lupane-type triterpenes lupeol (1), betulin (2), and methyl betulinate (7), glycosides (beta-D-glucosides, alpha-L-rhamnosides, and alpha-D-arabinosides) were synthesized and in vitro tested for cytotoxicity against three cancerous (A-549, DLD-1, and B16-F1) and one healthy (WS1) cell lines. The addition of a sugar moiety at the C-3 or C-28 position of betulin (2) resulted in a loss of cytotoxicity. In contrast, the 3-O-beta-D-glucosidation of lupeol (1) improved the activity by 7- to 12-fold (IC50 14-15.0 mu M). Moreover, the results showed that cancer cell lines are 8- to 12-fold more sensitive to the 3-O-alpha-L-rhamnopyranoside derivative of betulinic acid (IC50 2.6-3.9 mu M, 22) than the healthy cells (IC50 31 mu M). Thus, this study indicates that 3-O-glycosides of lupane-type triterpenoids represent an interesting class of potent in vitro cytotoxic agents. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis, cytotoxicity, and haemolytic activity of chacotrioside lupane-type neosaponins and their germanicane-type rearrangement products
  作者：Charles Gauthier、Jean Legault、Marianne Piochon、Serge Lavoie、Samuel Tremblay、André Pichette

  DOI：10.1016/j.bmcl.2009.02.076

  日期：2009.4

  The concise synthesis, via a stepwise glycosylation approach, of lupeol, betulin and betulinic acid O-glycosides bearing a chacotriosyl moiety at the C-3 position is described. All neosaponins as well as their rearrangement products of the germanicane-type were evaluated in vitro for their anticancer and haemolytic activities. Although betulinic acid and betulin 3 beta-O-chacotriosides were neither cytotoxic nor haemolytic, their rearrangement products allobetulin and 28-oxoallobetulin 3 beta-O-chacotriosides (9 and 10) exhibited a cytotoxicity pro. le up to fourfold superior to betulinic acid against human breast (MCF7) and prostate (PC-3) adenocarcinomas cell lines (IC(50) = 10-18 mu M). One important result was that only chacotriosides featuring non-polar functions at the C-28 position (6, 9 and 10) exerted a haemolytic activity against red blood cells. (c) 2009 Elsevier Ltd. All rights reserved.