junceelloside E | 1426853-24-8

• 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: junceelloside E
• 英文别名: [(6R)-6-[(3S,8S,9S,10S,13R,14S,17R)-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-3-methylideneheptan-2-yl] acetate
• CAS: 1426853-24-8
• 化学式: C₃₅H₅₆O₈
• 分子量: 604.825
• InChiKey: ZYMGKPINQYAUBH-ZIGDAWAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  junceelloside E 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 L-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.