5β,14β,16β-trihydroxy-19-oxo-3β-[(α-L-rhamnopyranosyl)oxy]bufa-20,22-dienolide

• 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: 5β,14β,16β-trihydroxy-19-oxo-3β-[(α-L-rhamnopyranosyl)oxy]bufa-20,22-dienolide
• 英文别名: 16β-hydroxyhellebrigenin-3-O-α-L-rhamnoside；(3S,5S,8R,9S,10S,13R,14S,16S,17R)-5,14,16-trihydroxy-13-methyl-17-(6-oxopyran-3-yl)-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• 化学式: C₃₀H₄₂O₁₁
• 分子量: 578.657
• InChiKey: QRFYVPVSGUSPHI-SEIYVQFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  41
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  183
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 5β,14β,16β-trihydroxy-19-oxo-3β-[(α-L-rhamnopyranosyl)oxy]bufa-20,22-dienolide 在 吡啶 作用下， 反应 20.0h， 以2.1 mg的产率得到Acetic acid (3S,5S,8R,9S,10S,13R,14S,16S,17R)-10-formyl-5,14-dihydroxy-13-methyl-17-(6-oxo-6H-pyran-3-yl)-3-((2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-16-yl ester
  参考文献：
  名称：

  Bufadienolide and Spirostanol Glycosides from the Rhizomes of Helleborus orientalis

  摘要：

  The rhizomes of Helleborus orientalis have been analyzed for the bufadienolide glycoside and spirostanol saponin constituents, resulting in the isolation of a new bufadienolide rhamnoside (1), along with two known bufadienolide glycosides (2 and 3) and five new spirostanol saponins (4-8). The structures of the new compounds were determined on the basis of extensive spectroscopic analysis, including 2D NMR, and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activities against cultured tumor and normal cells.

  DOI：

  10.1021/np0203638

文献信息

• Bufadienolide and Spirostanol Glycosides from the Rhizomes of <i>Helleborus </i><i>o</i><i>rientalis</i>
  作者：Kazuki Watanabe、Yoshihiro Mimaki、Hiroshi Sakagami、Yutaka Sashida

  DOI：10.1021/np0203638

  日期：2003.2.1

  The rhizomes of Helleborus orientalis have been analyzed for the bufadienolide glycoside and spirostanol saponin constituents, resulting in the isolation of a new bufadienolide rhamnoside (1), along with two known bufadienolide glycosides (2 and 3) and five new spirostanol saponins (4-8). The structures of the new compounds were determined on the basis of extensive spectroscopic analysis, including 2D NMR, and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activities against cultured tumor and normal cells.