(25R)-5α-spirostane-1β,3β-diol | 16963-78-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (25R)-5α-spirostane-1β,3β-diol
• 英文别名: brisbagenin；(25R)-5α-Spirostan-1β,3β-diol；(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13S,14R,16R,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-14,16-diol
• CAS: 16963-78-3
• 化学式: C₂₇H₄₄O₄
• 分子量: 432.644
• InChiKey: NCLLSOCDVMFDSK-FTGINFJWSA-N

物化性质

• 沸点：
  550.5±40.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 生成 (25R)-5α-spirostane-1β,3β-diol
  参考文献：
  名称：

  Lapin; Sannie, Bulletin de la Societe Chimique de France, 1955, p. 1552,1554

  摘要：

  DOI：

文献信息

• Steroidal saponins from the tubers of Dichelostemma multiflorum and their inhibitory activity on cyclic-amp phosphodiesterase
  作者：T Inoue

  DOI：10.1016/0031-9422(95)00117-p

  日期：1995.7

  Phytochemical examination of the tubers of Dichelostemma multiflorum led to the isolation of three new steroidal saponins together with two known saponins. The structures of the new compounds were determined by spectral data and a few chemical transformations to be (25R)-5 alpha-spirostane- 1 beta,3 beta-diol (brisbagenin) 1-O-[O-alpha-L-rhamnopyranosyl-(1-->3)-4-O- acetyl-alpha-L-arabinopyranoside]

  对多花草的块茎进行植物化学检查，分离出三种新的甾体皂苷和两种已知的皂苷。新化合物的结构由光谱数据和一些化学转化确定为 (25R)-5 α-螺甾烷- 1 β,3 β-二醇 (brisbagenin) 1-O-[O-α-L-rhamnopyranosyl- (1-->3)-4-O-乙酰-α-L-阿拉伯吡喃糖苷]，brisgabenin 1-O-[O-α-L-鼠李糖基-(1-->2)-O-[α-L-鼠李糖基-(1-->3)]-4-O-乙酰-α-L-阿拉伯吡喃糖苷e]和(22S,25S)-5 α-spirostan-3β-o1 3-O-[O-β-D -吡喃半乳糖基-(1-->2)-O-[β-D-吡喃木糖基-(1-->3)]-O-β-D-吡喃葡萄糖基-(1-->4)-β-D-吡喃半乳糖苷]。已知化合物被鉴定为 desglucolanatigonin II 和 gitonin，具有一定数量的相应 C-25S
• 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.
• Lapin; Sannie, Bulletin de la Societe Chimique de France, 1955, p. 1552,1554
  作者：Lapin、Sannie

  DOI：——

  日期：——