diosgenyl 4''-O-acetyl-α-L-rhamnopyranosyl-(1->2)-6'-O-acetyl-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: diosgenyl 4''-O-acetyl-α-L-rhamnopyranosyl-(1->2)-6'-O-acetyl-β-D-glucopyranoside
• 英文别名: diosgenyl 4r-O-acetyl-α-L-rhamnopyranosyl-(1->2)-6'-O-acetyl-β-D-glucopyranoside；diosgenyl 4-O-acetyl-α-L-rhamnopyranosyl-(1->2)-6-O-acetyl-β-D-glucopyranoside；[(2R,3S,4S,5R,6R)-5-[(2S,3R,4S,5R,6S)-5-acetyloxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-3,4-dihydroxy-6-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxyoxan-2-yl]methyl acetate
• 化学式: C₄₃H₆₆O₁₄
• 分子量: 806.989
• InChiKey: GSKHAUHYVZBUAJ-FDINGIDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  57
• 可旋转键数：
  9
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  189
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  乙酸乙烯酯 、 重楼皂苷E 在 novozyme 435 作用下， 以 四氢呋喃 为溶剂， 生成 diosgenyl α-L-rhamnopyranosyl-(1->2)-6'-O-acetyl-β-D-glucopyranoside 、 diosgenyl 4''-O-acetyl-α-L-rhamnopyranosyl-(1->2)-6'-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of novel spirostanic saponins and their cytotoxic activity

  摘要：

  This study was carried out to assess the cytotoxicity of several new synthetic steroidal saponins against the human myeloid leukemia cell lines (HL-60 and U937) and against human melanoma cells (SK-MEL-1). Several diosgenyl glycosides analyzed showed strong cell growth inhibition which was associated with alterations in cell cycle progression and induction of apoptosis. Studies of cytochrome c release and caspase-9 activation suggest a main role of the intrinsic pathway of apoptosis in the mechanism of cytotoxicity caused by this kind of compounds. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.089

文献信息

• Lipase-catalyzed regioselective acylation of diosgenyl saponins
  作者：Biao Yu、Guowen Xing、Yongzheng Hui、Xiuwen Han

  DOI：10.1016/s0040-4039(01)01051-6

  日期：2001.8

  Diosgenyl saponins were regio selectively acylated by Novozyme 435 with vinyl esters as acylating agents in THF to afford the corresponding mono- or diacyl diosgenyl saponins. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of novel spirostanic saponins and their cytotoxic activity
  作者：Juan C. Hernández、Francisco León、Ignacio Brouard、Fernando Torres、Sara Rubio、José Quintana、Francisco Estévez、Jaime Bermejo

  DOI：10.1016/j.bmc.2007.10.089

  日期：2008.2.15

  This study was carried out to assess the cytotoxicity of several new synthetic steroidal saponins against the human myeloid leukemia cell lines (HL-60 and U937) and against human melanoma cells (SK-MEL-1). Several diosgenyl glycosides analyzed showed strong cell growth inhibition which was associated with alterations in cell cycle progression and induction of apoptosis. Studies of cytochrome c release and caspase-9 activation suggest a main role of the intrinsic pathway of apoptosis in the mechanism of cytotoxicity caused by this kind of compounds. (c) 2007 Elsevier Ltd. All rights reserved.