3-O-{[β-D-glucopyranosyl(1->6)]-β-D-glucopyranosyl}-26-O-β-D-glucopyranosyl-(25S)-5β-furostane-3β,22,26-triol

• 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: 3-O-{[β-D-glucopyranosyl(1->6)]-β-D-glucopyranosyl}-26-O-β-D-glucopyranosyl-(25S)-5β-furostane-3β,22,26-triol
• 英文别名: sarsaparilloside C；(25S)-26-O-β-D-glucopyranosyl-22-hydroxy-5β-furostane-3β,26-diol-3-O-β-D-glucopyranosyl-(1->6)-β-D-glucopyranoside；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(1R,2S,4S,6R,7S,8R,9S,12S,13S,16S,18R)-6-hydroxy-7,9,13-trimethyl-6-[(3S)-3-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosan-16-yl]oxy]oxan-2-yl]methoxy]oxane-3,4,5-triol
• 化学式: C₄₅H₇₆O₁₉
• 分子量: 921.087
• InChiKey: XDJRIVOSNYPOEY-RMKOBKJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  64
• 可旋转键数：
  13
• 环数：
  8.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  307
• 氢给体数：
  12
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  甲醇 、 3-O-{[β-D-glucopyranosyl(1->6)]-β-D-glucopyranosyl}-26-O-β-D-glucopyranosyl-(25S)-5β-furostane-3β,22,26-triol 生成 甲基-Alpha-D-吡喃葡糖苷
  参考文献：
  名称：

  Steroidal saponins from the roots of Smilax sp.: Structure and bioactivity

  摘要：

  Phytochemical characterization of a commercial herb sample supplied as Smilax ornata Lem. (sarsaparilla) led to the isolation of five steroidal saponins, including two new furostanol saponins sarsaparillo-side B (1) and sarsaparilloside C (2), whose structures were elucidated via a combination of multistage mass spectrometry (MSn), 1D and 2D NMR experiments, and chemical degradation. The previously unreported spectroscopic characterization of sarsaparilloside (3), Delta(20(22))-sarsaparilloside (4), and parillin (5) is also provided. The antiproliferative activity of the isolated saponins was compared in six human cell lines derived from different tumor types and one of the structures (2) was particularly active against the HT29 colon tumor cell line. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.01.009
• 作为产物：
  描述：

  在 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 以96%的产率得到3-O-{[β-D-glucopyranosyl(1->6)]-β-D-glucopyranosyl}-26-O-β-D-glucopyranosyl-(25S)-5β-furostane-3β,22,26-triol
  参考文献：
  名称：

  [EN] SYNTHESIS OF TIMOSAPONIN BII
  [FR] SYNTHÈSE DE TIMOSAPONINE BII

  摘要：

  这项发明提供了从山楂皂苷到泰莫沙皂苷BII及相关化合物的合成途径。提供了一种二酮中间体，可以优点地用于在所需的糖苷末端产物的复杂糖基的原位组装。然后，使用硼氢化还原剂选择性地还原二酮化合物，形成所需的最终产物，其中某些最终产物和中间体是新颖的化合物。

  公开号：

  WO2009132478A1

文献信息

• Steroidal saponins from the roots of Smilax sp.: Structure and bioactivity
  作者：Victoria L. Challinor、Peter G. Parsons、Sonet Chap、Eve F. White、Joanne T. Blanchfield、Reginald P. Lehmann、James J. De Voss

  DOI：10.1016/j.steroids.2012.01.009

  日期：2012.4

  Phytochemical characterization of a commercial herb sample supplied as Smilax ornata Lem. (sarsaparilla) led to the isolation of five steroidal saponins, including two new furostanol saponins sarsaparillo-side B (1) and sarsaparilloside C (2), whose structures were elucidated via a combination of multistage mass spectrometry (MSn), 1D and 2D NMR experiments, and chemical degradation. The previously unreported spectroscopic characterization of sarsaparilloside (3), Delta(20(22))-sarsaparilloside (4), and parillin (5) is also provided. The antiproliferative activity of the isolated saponins was compared in six human cell lines derived from different tumor types and one of the structures (2) was particularly active against the HT29 colon tumor cell line. (C) 2012 Elsevier Inc. All rights reserved.
• [EN] SYNTHESIS OF TIMOSAPONIN BII<br/>[FR] SYNTHÈSE DE TIMOSAPONINE BII
  申请人：PHYTOPHARM PLC

  公开号：WO2009132478A1

  公开（公告）日：2009-11-05

  The invention provides a synthetic route from sarsasapogenin to timosaponin BII and related compounds.A diketone intermediate is provided, which can advantageously be used for in situ assembly of complex sugar moieties of the desired glycone end product. The diketone compound is then selectively reduced using a borohydride reducing agent to form the desired end product, certain of the end products and intermediates are novel compounds perse.

  这项发明提供了从山楂皂苷到泰莫沙皂苷BII及相关化合物的合成途径。提供了一种二酮中间体，可以优点地用于在所需的糖苷末端产物的复杂糖基的原位组装。然后，使用硼氢化还原剂选择性地还原二酮化合物，形成所需的最终产物，其中某些最终产物和中间体是新颖的化合物。