Δ(20(22))-sarsaparilloside | 24332-93-2

• 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: Δ(20(22))-sarsaparilloside
• 英文别名: δ20(22)-sarsaparilloside
• CAS: 24332-93-2
• 化学式: C₅₇H₉₄O₂₇
• 分子量: 1211.36
• InChiKey: KPKMIXGAKPDMQM-YTQIBFCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.15
• 重原子数：
  84.0
• 可旋转键数：
  18.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  425.21
• 氢给体数：
  16.0
• 氢受体数：
  27.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 Δ(20(22))-sarsaparilloside 生成 甲基-Alpha-D-吡喃葡糖苷 、 甲基6-脱氧吡喃己糖苷
  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

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.