longifolioside B

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: longifolioside B
• 英文别名: [(1S,4aR,5S,6R,7S,7aS)-6-chloro-7-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] 3-(3,4-dihydroxyphenyl)prop-2-enoate
• 化学式: C₂₄H₂₉ClO₁₃
• 分子量: 560.939
• InChiKey: ROWOUKGALGILKZ-XTUIDLEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  216
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  longifolioside B 在 sodium hydroxide 作用下， 以 water-d2 为溶剂， 反应 24.0h， 生成 梓醇
  参考文献：
  名称：

  Chlorinated Iridoid Glucosides from Veronica longifolia and Their Antioxidant Activity

  摘要：

  From Veronica longifolia were isolated three chlorinated iridoid glucosides, namely, asystasioside E (6) and its 6-O-esters 6a and 6b, named longifoliosides A and B, respectively. The structures of 6a and 6b were proved by analysis of their spectroscopic data and by conversion to the catalpol ester verproside (5a) or to catalpol (5), respectively. The configuration of the previously known vanilloyl analogue, urphoside B, was shown to be the 6 beta-epimer (6c) of the structure originally reported. Longifoliosides A (6a) and B (6b) were found to exhibit radical-scavenging activity against nitric oxide, superoxide, and 2,2-diphenyl-1-picrylhydrazyl radicals.

  DOI：

  10.1021/np100366k

文献信息

• Chlorinated Iridoid Glucosides from <i>Veronica longifolia</i> and Their Antioxidant Activity
  作者：Søren R. Jensen、Charlotte H. Gotfredsen、U. Sebnem Harput、Iclal Saracoglu

  DOI：10.1021/np100366k

  日期：2010.9.24

  From Veronica longifolia were isolated three chlorinated iridoid glucosides, namely, asystasioside E (6) and its 6-O-esters 6a and 6b, named longifoliosides A and B, respectively. The structures of 6a and 6b were proved by analysis of their spectroscopic data and by conversion to the catalpol ester verproside (5a) or to catalpol (5), respectively. The configuration of the previously known vanilloyl analogue, urphoside B, was shown to be the 6 beta-epimer (6c) of the structure originally reported. Longifoliosides A (6a) and B (6b) were found to exhibit radical-scavenging activity against nitric oxide, superoxide, and 2,2-diphenyl-1-picrylhydrazyl radicals.