(20S, 22R)-spirost-25(27)-en-1β, 2β, 3β, 4β, 5β-pentaol-5-O-β-D-glucopyranoside | 288255-57-2

• 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: (20S, 22R)-spirost-25(27)-en-1β, 2β, 3β, 4β, 5β-pentaol-5-O-β-D-glucopyranoside
• 英文别名: spirost-25(27)-en-1beta,2beta,3beta,4beta,5beta-pentol-5-O-beta-d-glucopyranoside；(1S,2S,4S,6R,7S,8R,9S,12S,13S,14S,15S,16S,17S,18R)-7,9,13-trimethyl-5'-methylidene-18-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-14,15,16,17-tetrol
• CAS: 288255-57-2
• 化学式: C₃₃H₅₂O₁₂
• 分子量: 640.769
• InChiKey: XBJXKPFBJMQGQF-RDNNGMMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  45
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  199
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (20S, 22R)-spirost-25(27)-en-1β, 2β, 3β, 4β, 5β-pentaol-5-O-β-D-glucopyranoside 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 可得然胶 、 Δ ²⁵⁽²⁷⁾-pentrogenin
  参考文献：
  名称：

  Steroids from herbs of Reineckia carnea and their anticomplement activities

  摘要：

  A new polyhydroxylated pregnane, named l beta,2 beta,3 beta,4 beta,5 beta,6 beta-hexolhydroxy-pregn-16-en-20-one (1), along with nine known (2-10) steroidal saponins were isolated from the whole plant of Reineckia carnea. Structure elucidations of all compounds were established by interpretation of their NMR spectral data, HR-ESI-MS and comparing with literatures. In addition, these compounds were evaluated with anticomplement activity. The result showed that compound 1 exhibited anticomplement effects with the CH50 values of 0.043 mg/mL, but saponins (2-10) showed no inhibition. Interestingly, hydrolysis of steroidal saponins (2-10) resulted in its aglycones (2a-10a) correspondingly which showed anticomplement activity with the CH50 values of 0.049-0.156 mg/mL.[GRAPHICS].

  DOI：

  10.1080/14786419.2017.1423309

文献信息

• Steroids from herbs of <i>Reineckia carnea</i> and their anticomplement activities
  作者：Xu Xu、Bei Wu、Yanzhi Zhan、Wenping Huang、Shilin Yang、Quan Wen、Yulin Feng

  DOI：10.1080/14786419.2017.1423309

  日期：2019.6.3

  A new polyhydroxylated pregnane, named l beta,2 beta,3 beta,4 beta,5 beta,6 beta-hexolhydroxy-pregn-16-en-20-one (1), along with nine known (2-10) steroidal saponins were isolated from the whole plant of Reineckia carnea. Structure elucidations of all compounds were established by interpretation of their NMR spectral data, HR-ESI-MS and comparing with literatures. In addition, these compounds were evaluated with anticomplement activity. The result showed that compound 1 exhibited anticomplement effects with the CH50 values of 0.043 mg/mL, but saponins (2-10) showed no inhibition. Interestingly, hydrolysis of steroidal saponins (2-10) resulted in its aglycones (2a-10a) correspondingly which showed anticomplement activity with the CH50 values of 0.049-0.156 mg/mL.[GRAPHICS].