24-methylenecycloartane-3β,6β,16β-triol 3-Oβ-D-xylopyranoside | 1382805-62-0

• 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: 24-methylenecycloartane-3β,6β,16β-triol 3-Oβ-D-xylopyranoside
• 英文别名: (2S,3R,4S,5R)-2-[[(1S,3R,6S,8R,9R,11S,12S,14S,15R,16R)-9,14-dihydroxy-7,7,12,16-tetramethyl-15-[(2R)-6-methyl-5-methylideneheptan-2-yl]-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]oxane-3,4,5-triol
• CAS: 1382805-62-0
• 化学式: C₃₆H₆₀O₇
• 分子量: 604.868
• InChiKey: ADLCMRZYZGDAKH-QHVZBMNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  43
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  24-methylenecycloartane-3β,6β,16β-triol 3-Oβ-D-xylopyranoside 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 D-木糖
  参考文献：
  名称：

  Cycloartane-Type Triterpenes from the Leaves of Homonoia riparia with VEGF-Induced Angiogenesis Inhibitory Activity

  摘要：

  Six new cycloartane-type triterpenes (1-6), 24-methylenecydoartane-3 beta,6 beta,7 beta-triol (1), 24-methylenecycloartane-3 beta,6 beta,7 beta,16 beta-tetraol (2), 24-methylenecycloartane-3 beta,6 beta,16 beta-triol (3), 24-methylenecycloartane-3 beta,7 beta,16 beta-triol 3-O-beta-D-xylopyranoside (4), 24-methylenecycloartane-3 beta,6 beta,16 beta-triol 3-O-beta-D-xylopyranoside (5), and 24-methylenecycloartane-3 beta,6 beta,7 beta-triol 3-O-beta-D-xylopyranoside (6), were isolated from the leaves of Homonoia riparia, together with one known compound, 24-methylenecycloartarie-3 beta,6 beta,7 beta,16 beta-tetraol 3-O-beta-D-xylopyranoside (7). The structures of the new triterpenes were established by spectroscopic studies and from chemical evidence, and the inhibitory effects of compounds 1 and 3-7 on VEGF-induced vascular permeability were examined in vivo in rats using the Miles assay. In addition, the inhibitory effect of 7 on VEGF-induced tube formation by HUVECs in vitro was investigated.

  DOI：

  10.1021/np300224k

文献信息

• Cycloartane-Type Triterpenes from the Leaves of <i>Homonoia riparia</i> with VEGF-Induced Angiogenesis Inhibitory Activity
  作者：IkSoo Lee、Junghyun Kim、Young Sook Kim、Nam Hee Yoo、Chan-Sik Kim、Kyuhyung Jo、Joo-Hwan Kim、Tran The Bach、Jin Sook Kim

  DOI：10.1021/np300224k

  日期：2012.7.27

  Six new cycloartane-type triterpenes (1-6), 24-methylenecydoartane-3 beta,6 beta,7 beta-triol (1), 24-methylenecycloartane-3 beta,6 beta,7 beta,16 beta-tetraol (2), 24-methylenecycloartane-3 beta,6 beta,16 beta-triol (3), 24-methylenecycloartane-3 beta,7 beta,16 beta-triol 3-O-beta-D-xylopyranoside (4), 24-methylenecycloartane-3 beta,6 beta,16 beta-triol 3-O-beta-D-xylopyranoside (5), and 24-methylenecycloartane-3 beta,6 beta,7 beta-triol 3-O-beta-D-xylopyranoside (6), were isolated from the leaves of Homonoia riparia, together with one known compound, 24-methylenecycloartarie-3 beta,6 beta,7 beta,16 beta-tetraol 3-O-beta-D-xylopyranoside (7). The structures of the new triterpenes were established by spectroscopic studies and from chemical evidence, and the inhibitory effects of compounds 1 and 3-7 on VEGF-induced vascular permeability were examined in vivo in rats using the Miles assay. In addition, the inhibitory effect of 7 on VEGF-induced tube formation by HUVECs in vitro was investigated.