25-O-acetyl-3-O-[β-D-arabinopyranosyl]-(22E)-cholesta-5,22-diene-3β,19,25-triol

• 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: 25-O-acetyl-3-O-[β-D-arabinopyranosyl]-(22E)-cholesta-5,22-diene-3β,19,25-triol
• 英文别名: junceelloside F
• 化学式: C₃₄H₅₄O₈
• 分子量: 590.798
• InChiKey: CZZKKUDARYMHPQ-WZQNRVSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  125.68
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  25-O-acetyl-3-O-[β-D-arabinopyranosyl]-(22E)-cholesta-5,22-diene-3β,19,25-triol 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 阿拉伯糖
  参考文献：
  名称：

  Steroids Glycosylated with Both d- and l-Arabinoses from the South China Sea Gorgonian Dichotella gemmacea

  摘要：

  Three new 19-hydroxy steroidal glycosides, namely, junceellosides E-G (2-4), were isolated together with the known analogue junceelloside C (1) from the South China Sea gorgonian Dichotella gemmacea. The structures of these compounds were elucidated by a combination of detailed spectroscopic analyses, chemical methods, and comparison with reported data. These glycosides are found to have sugar moieties of both beta-L- and beta-D-arabinopyranoses by HPLC analysis of their thiocarbamoylthiazolidine derivatives and those of authentic D- and L-arabinoses, leading to the structure revision of junceelloside C (1). This is the first report of steroidal glycosides from the gorgonian D. gemmacea and the first report of glycosides with beta-L-arabinopyranose from marine sources.

  DOI：

  10.1021/np300906b

文献信息

• Steroids Glycosylated with Both <scp>d</scp>- and <scp>l</scp>-Arabinoses from the South China Sea Gorgonian <i>Dichotella gemmacea</i>
  作者：Mei Jiang、Peng Sun、Hua Tang、Bao-Shu Liu、Tie-Jun Li、Cui Li、Wen Zhang

  DOI：10.1021/np300906b

  日期：2013.4.26

  Three new 19-hydroxy steroidal glycosides, namely, junceellosides E-G (2-4), were isolated together with the known analogue junceelloside C (1) from the South China Sea gorgonian Dichotella gemmacea. The structures of these compounds were elucidated by a combination of detailed spectroscopic analyses, chemical methods, and comparison with reported data. These glycosides are found to have sugar moieties of both beta-L- and beta-D-arabinopyranoses by HPLC analysis of their thiocarbamoylthiazolidine derivatives and those of authentic D- and L-arabinoses, leading to the structure revision of junceelloside C (1). This is the first report of steroidal glycosides from the gorgonian D. gemmacea and the first report of glycosides with beta-L-arabinopyranose from marine sources.