(25R)-3β-hydroxyspirost-5-en-1β-yl 3-O-α-L-rhamnopyranosyl-(1->2)-O-β-D-xylopyranosyl-(1->3)-α-L-arabinopyranoside

• 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: (25R)-3β-hydroxyspirost-5-en-1β-yl 3-O-α-L-rhamnopyranosyl-(1->2)-O-β-D-xylopyranosyl-(1->3)-α-L-arabinopyranoside
• 英文别名: (25R)-3β-hydroxyspirost-5-en-1β-yl O-α-L-rhamnopyranosyl-(1->2)-O-[β-D-xylopyranosyl-(1->3)]-α-L-arabinopyranoside；(2S,3R,4R,5R,6S)-2-[(2S,3R,4S,5S)-5-hydroxy-2-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,14R,16R)-16-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-14-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• 化学式: C₄₃H₆₈O₁₆
• 分子量: 841.003
• InChiKey: KQUKDOSYQGPURW-VQCUNOQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  59
• 可旋转键数：
  6
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  236
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (25R)-3β-hydroxyspirost-5-en-1β-yl 3-O-α-L-rhamnopyranosyl-(1->2)-O-β-D-xylopyranosyl-(1->3)-α-L-arabinopyranoside 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以0.6 mg的产率得到鲁斯可皂苷元
  参考文献：
  名称：

  New Neuritogenic Steroidal Saponin fromOphiopogon japonicus(Thunb.) Ker-Gawl

  摘要：

  从麦冬中分离出一种新的类固醇皂苷。该皂苷在糖的C-4′位置的羼基上进行了2-羟基-3-甲基戊酸基的修饰，并连接到苷元的C-1上。它对PC12细胞表现出显著的神经突起生成活性。结构-活性关系分析表明，苷元而非糖基和酰化在神经突起生成活性中具有重要作用。

  DOI：

  10.1271/bbb.110066
• 作为产物：
  描述：

  [(3S,4S,5R,6S)-6-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,14R,16R)-16-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-14-yl]oxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl] (2S,3S)-2-hydroxy-3-methylpentanoate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以1.8 mg的产率得到(25R)-3β-hydroxyspirost-5-en-1β-yl 3-O-α-L-rhamnopyranosyl-(1->2)-O-β-D-xylopyranosyl-(1->3)-α-L-arabinopyranoside
  参考文献：
  名称：

  New Neuritogenic Steroidal Saponin fromOphiopogon japonicus(Thunb.) Ker-Gawl

  摘要：

  从麦冬中分离出一种新的类固醇皂苷。该皂苷在糖的C-4′位置的羼基上进行了2-羟基-3-甲基戊酸基的修饰，并连接到苷元的C-1上。它对PC12细胞表现出显著的神经突起生成活性。结构-活性关系分析表明，苷元而非糖基和酰化在神经突起生成活性中具有重要作用。

  DOI：

  10.1271/bbb.110066

文献信息

• Steroidal Glycosides from the Bulbs of <i>Ornithogalum </i><i>t</i><i>hyrsoides</i>
  作者：Minpei Kuroda、Yoshihiro Mimaki、Kazutomo Ori、Hiroshi Sakagami、Yutaka Sashida

  DOI：10.1021/np040108i

  日期：2004.10.1

  Phytochemical analyses have been carried out on the fresh bulbs of Ornithogalum thyrsoides with particular attention to the steroidal glycoside constituents, resulting in the isolation of four new spirostanol saponins and seven new cholestane glycosides, together with three known steroidal compounds. The structures of the new glycosides were determined on the basis of their spectroscopic data, including 2D NMR spectroscopy, and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activities against HL-60 human promyelocytic leukemia cells and HSC-2 human oral squamous cell carcinoma cells.
• New Neuritogenic Steroidal Saponin from<i>Ophiopogon japonicus</i>(Thunb.) Ker-Gawl
  作者：Yuan QU、Yang ZHANG、Liang PEI、Yan WANG、Lijuan GAO、Qianming HUANG、Makoto OJIKA、Youji SAKAGAMI、Jianhua QI

  DOI：10.1271/bbb.110066

  日期：2011.6.23

  A new steroidal saponin was isolated from Ophiopogon japonicus. This saponin possesses a modification by 2-hydroxy-3-methylvalerylation of the hydroxyl group at C-4′ of the sugar, linked to C-1 of the aglycone. It exhibited significant neuritogenic activity for PC12 cells. The structure-activity relationship revealed the aglycone, rather than the sugar moieties and acylation, to be important for the neuritogenic activity.

  从麦冬中分离出一种新的类固醇皂苷。该皂苷在糖的C-4′位置的羼基上进行了2-羟基-3-甲基戊酸基的修饰，并连接到苷元的C-1上。它对PC12细胞表现出显著的神经突起生成活性。结构-活性关系分析表明，苷元而非糖基和酰化在神经突起生成活性中具有重要作用。