sitosterol 3-O-{α-L-rhamnopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-galactopyranoside} | 1269649-02-6

• 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: sitosterol 3-O-{α-L-rhamnopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-galactopyranoside}
• 英文别名: (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-2-[[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 1269649-02-6
• 化学式: C₄₆H₇₈O₁₄
• 分子量: 855.117
• InChiKey: HSDQMYOKNFNKMQ-LESKHTKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  60
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  217
• 氢给体数：
  8
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 sitosterol 3-O-{α-L-rhamnopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-galactopyranoside}
  参考文献：
  名称：

  Efficient synthesis of trisaccharide saponins and their tumor cell killing effects through oncotic necrosis

  摘要：

  To investigate the relationship of cytotoxicity and saponins with varied aglycones, based on the structure of indioside E 1, a natural derived anti-tumor active ingredient from Chinese medicinal plant Solanum indicum L., five novel saponins 2-6 bearing the same trisaccharide moiety together with 1 were efficiently synthesized via a transglycosylation strategy. MTT assay revealed the killing effects to tumor cells of the synthesized saponins are varied with the change of aglycones. Furthermore, time-lapse microscopy, LDH release, PI staining, and immunocytochemical investigations demonstrated that the cell death caused by neosaponin 2 was through oncotic necrosis involving plasma membrane perturbation and destruction of cytoskeleton. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.046