3-O-β-D-glucopyranosylbetulin | 40653-05-2

• 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: 3-O-β-D-glucopyranosylbetulin
• 英文别名: betulin 3-O-β-D-glucopyranoside；betulin-3-yl β-D-glucoside；betulin-3-yl β-D-glucopyranoside；Betulin-3-yl beta-glucopyranoside；(2R,3R,4S,5S,6R)-2-[[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 40653-05-2
• 化学式: C₃₆H₆₀O₇
• 分子量: 604.868
• InChiKey: FOMHDOVMNXLOCJ-BGYDQFIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  43
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,2,3,4,6-戊-O-苯甲酰基-D-吡喃葡萄糖苷 在 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 氢溴酸 、 caesium carbonate 、 溶剂黄146 、 silver carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 11.5h， 生成 3-O-β-D-glucopyranosylbetulin
  参考文献：
  名称：

  Glycosidation of lupane-type triterpenoids as potent in vitro cytotoxic agents

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2006.05.075

文献信息

• Synthesis and structure–activity relationship study of cytotoxic germanicane- and lupane-type 3β-O-monodesmosidic saponins starting from betulin
  作者：Dominic Thibeault、Charles Gauthier、Jean Legault、Jimmy Bouchard、Philippe Dufour、André Pichette

  DOI：10.1016/j.bmc.2007.06.033

  日期：2007.9

  triterpenes betulin (1) and betulinic acid (2), respectively. The medical uses of betulinic acid (2) and its derivatives are limited because of their poor hydrosolubility and pharmacokinetics properties. In order to overcome this major problem, we synthesized and studied the in vitro anticancer activity of a series of 3beta-O-monodesmosidic saponins derived from betulin (14-16), betulinic acid (20-22)

  可以通过Wagner-Meerwein重排分别获得更广泛的丁烷型三萜白桦蛋白（1）和桦木酸（2）来获得锗烷型三萜烯别白蛋白（3）和28-氧脂球蛋白（4）。桦木酸（2）及其衍生物的医学用途因其水溶性差和药代动力学特性差而受到限制。为了克服这个主要问题，我们合成并研究了一系列由桦木素（14-16），桦木酸（20-22），同素白蛋白（23-28）衍生的3β-O-单去糖苷皂苷的体外抗癌活性。以及基于六个不同天然糖残基（d-葡萄糖，l-鼠李糖，d-阿拉伯糖，d-半乳糖，d-甘露糖和d-木糖）的28-氧脂球蛋白（29-34）。这项结构与活性之间的关系研究证实，桦木酸皂苷通常比衍生自桦木素的体外抗癌药更好，但桦木素3β-O-α-d-甘露吡喃糖苷除外（15），对肺癌具有有效的细胞毒性作用（ A-549）和大肠腺癌（DLD-1）人细胞系，IC（50）范围为7.3至10.1μmol/ L。此外，尽管成功合成了
• Glycosylation of betulin and its acetates in the presence of cadmium carbonate
  作者：L. �. Odinokova、G. I. Oshitok、V. A. Denisenko、V. F. Anufriev、A. M. Tolkach、N. I. Uvarova

  DOI：10.1007/bf00579477

  日期：——
• Synthesis of Betulin-3-yl-β-D-Glucopyranoside
  作者：Guoling Zhao、Weidong Yan

  DOI：10.1080/07328300902887698

  日期：2009.5.22

  Two concise routes toward betulin-3-yl--D-glucopyranoside, being different in the protection of primary alcohol of betulin, were developed. The synthesis adopted a stepwise glycosidation method employing glycosyl trichloroacetimidate as donor.
• Hypolipidemic properties of betulin glycosides
  作者：A. S. Ivanov、T. S. Zakharova、L. É. Odinokova、N. I. Uvarova

  DOI：10.1007/bf01145561

  日期：1987.9
• 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.