loganin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: loganin
• 英文别名: methyl (1S,4aS,6S,7R,7aS)-6-acetyloxy-7-methyl-1-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(3,4,5-trimethoxybenzoyl)oxymethyl]oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• 化学式: C₃₅H₄₄O₁₈
• 分子量: 752.724
• InChiKey: VEDPZJPWKILDSR-DAGYHHOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  53
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  213
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  马钱子苷 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 79.0h， 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

文献信息

• A cytotoxic agent from Strychnos nux-vomica and biological evaluation of its modified analogues
  作者：M. Khan、A. Garg、S. K. Srivastava、M. P. Darokar

  DOI：10.1007/s00044-011-9832-9

  日期：2012.10

  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.