26-thiodiosgenin 3-O-α-L-arabinopyranoside | 1573154-41-2

• 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: 26-thiodiosgenin 3-O-α-L-arabinopyranoside
• 英文别名: (2S,3R,4S,5S)-2-[(1S,2S,4S,5'R,6S,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'-thiane]-16-yl]oxyoxane-3,4,5-triol
• CAS: 1573154-41-2
• 化学式: C₃₂H₅₀O₆S
• 分子量: 562.811
• InChiKey: JIOANKJHODAUFH-WSWUNJIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  39
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 26-thiodiosgenin 3-O-α-L-arabinopyranoside
  参考文献：
  名称：

  Synthesis and cytotoxic effect of pseudodiosgenyl saponins with thio-ring F

  摘要：

  Both the sugar moieties and aglycons of steroid saponins play important roles for their bioactivities. In order to test the biological contribution of the glycosyl residue and search new saponins with notable anticancer activity, mono- and di-saccharide pseudodiosgenyl saponins 22-28 together with two pseudodiosgenyl conjugates 29 and 30 were conveniently synthesized, all of which were based on the aglycon 7 bearing the thio-ring F. The cytotoxicity on human cancer cells (MCF-7, HepG-2, A549) for all of the synthesized compounds 7 and 22-30 was evaluated by MTT method. The thio-aglycon 7 when conjugated with sugars exhibited potent cytotoxicity, and the introduction of D-glucosamine into aglycon 7 led to the most potent compound 28. Furthermore, DAPI staining, AV/PI staining, AO-relocation, AO-uptake and LysoTracker Red-uptake assays demonstrated that the cell death caused by neosaponin 28 was at least partially through apoptosis involving lysosomal membrane permeabilization. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.055

文献信息

• Synthesis and cytotoxic effect of pseudodiosgenyl saponins with thio-ring F
  作者：Xin Zan、Jian Gao、Guofeng Gu、Shanshan Liu、Bin Sun、Lei Liu、Hong-Xiang Lou

  DOI：10.1016/j.bmcl.2014.01.055

  日期：2014.3

  Both the sugar moieties and aglycons of steroid saponins play important roles for their bioactivities. In order to test the biological contribution of the glycosyl residue and search new saponins with notable anticancer activity, mono- and di-saccharide pseudodiosgenyl saponins 22-28 together with two pseudodiosgenyl conjugates 29 and 30 were conveniently synthesized, all of which were based on the aglycon 7 bearing the thio-ring F. The cytotoxicity on human cancer cells (MCF-7, HepG-2, A549) for all of the synthesized compounds 7 and 22-30 was evaluated by MTT method. The thio-aglycon 7 when conjugated with sugars exhibited potent cytotoxicity, and the introduction of D-glucosamine into aglycon 7 led to the most potent compound 28. Furthermore, DAPI staining, AV/PI staining, AO-relocation, AO-uptake and LysoTracker Red-uptake assays demonstrated that the cell death caused by neosaponin 28 was at least partially through apoptosis involving lysosomal membrane permeabilization. (C) 2014 Elsevier Ltd. All rights reserved.