loganin

• 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: loganin
• 英文别名: 6'-O-Trityl loganin；methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(trityloxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• 化学式: C₃₆H₄₀O₁₀
• 分子量: 632.708
• InChiKey: CQODCQQDRHYARY-JQHSGQRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  46
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  loganin 在 吡啶 、 4-二甲氨基吡啶 、 溶剂黄146 作用下， 以 氯仿 、 水 为溶剂， 反应 43.0h， 生成 loganin
  参考文献：
  名称：

  A cytotoxic agent from Strychnos nux-vomica and biological evaluation of its modified analogues

  摘要：

  Although a number of chemicals have been isolated from Strychnos nux-vomica, only a few have been evaluated for their biological significance. As a part of our drug discovery programme for cytotoxic agents from Indian medicinal plants, a novel cytotoxic agent, loganin 1 was isolated from the fruit pulp of S. nux-vomica. The loganin 1 showed significant anticancer activity against the human liver (WRL-68), colon (COLO-320 and CaCo2), ovarian (PA-1) and breast (MCF-7) cancer cell lines. Loganin 1 was further chemically transformed into eleven semi-synthetic derivatives 2-12 of which 2',3',4',7-tetra-O-acetyl-6'-O-(3''', 4''', 5''')-trimethoxybenzoyl loganin 11 and 2',3',4',7-tetra-O-acetyl-6'-O-lauroyl loganin 6 derivatives showed eight, 13 and three times while 2',3',4',7-tetra-O-acetyl-6'-O-lauroyl loganin 6 showed equal, 13 and two times more activity against human suspension colon (CaCo2), adherent colon (COLO-320) and liver (WRL-68) cancer cell lines, respectively, than the known anticancer agent, vinblastine. The other analogues (except 4, 8 and 9) and loganin also showed marginal to moderate anticancer activity against the five tested human cancer cell lines.

  DOI：

  10.1007/s00044-011-9832-9
• 作为产物：
  描述：

  三苯基氯甲烷 、 马钱子苷 以 吡啶 为溶剂， 反应 36.0h， 以to give the compound 6′-O-trityl loganin (2) in 65% yield的产率得到loganin
  参考文献：
  名称：

  Loganin analogues and a process for the preparation thereof

  摘要：

  本发明提供了新型的洛甘醇类似物以及其制备方法。本发明还提供了从马钱子果肉中分离出的萜苷糖苷洛甘醇及其生物活性半合成类似物对体外培养的各种人类癌细胞系的应用。

  公开号：

  US07767798B2

文献信息

• Novel loganin analogues and a process for the preparation thereof
  申请人：Khanuja Preet Singh Suman

  公开号：US20070123474A1

  公开（公告）日：2007-05-31

  The present invention provides novel loganin analogues and a process for the preparation thereof. The present invention further provides the use of Iridoid glycoside loganin isolated from the fruit pulp of Strychnos nux - vomica and its bioactive semi-synthetic analogues against various human cancer cell lines grown in-vitro.

  本发明提供了新型的洛甘醇类似物及其制备方法。本发明还提供了从马钱子果肉中分离出的萜烯苷类物质洛甘醇及其生物活性半合成类似物对体外培养的各种人类癌细胞系的应用。