loganin pentaacetate | 180974-64-5

• 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 pentaacetate
• 英文别名: loganin；methyl (1S,4aS,6S,7R,7aS)-6-acetyloxy-7-methyl-1-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• CAS: 180974-64-5
• 化学式: C₂₅H₃₄O₁₄
• 分子量: 558.537
• InChiKey: ZWQDBTFTJQQTSP-UCMDCWNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  179
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  loganin pentaacetate 在 pyridinium chlorochromate 作用下， 以 苯 为溶剂， 以58%的产率得到methyl (1S,4aS,6S,7R,7aS)-6-acetyloxy-1-[[(2S,3R,4S)-3,4-diacetyloxy-6-formyl-3,4-dihydro-2H-pyran-2-yl]oxy]-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
  参考文献：
  名称：

  Raj; Mathad, Vijayavitthal T.; Bhaduri, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 10, p. 1056 - 1061

  摘要：

  DOI：
• 作为产物：
  描述：

  马钱子苷 在 吡啶 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 55.0h， 生成 loganin pentaacetate
  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

• Radioimmunoassay for the determination of loganin and the biotransformation of loganin to secologanin by plant cell cultures
  作者：Takao Tanahashi、Naotaka Nagakura、Hiroyuki Inouye、Meinhart H. Zenk

  DOI：10.1016/s0031-9422(00)84941-9

  日期：1984.8

  affinity ( K a = 1.6 × 10 9 1/mol) for loganin and permitted the detection of as little as 0.1 ng per 0.05 ml of sample. The antiserum was highly specific for loganin and its aglycone, with only 10-hydroxyloganin and 7-epi-loganin showing a substantial cross reactivity. A number of cell cultures of the Caprifoliaceae were tested for their ability to transform added loganin to secologanin. By labelled precursor

  摘要 已经开发了一种放射免疫分析技术，用于定量测量来自整株植物和培养植物细胞的新鲜和干燥材料的粗提取物中的马钱素。该测定利用 6'-羧基多糖苷，其通过与牛血清白蛋白连接而具有免疫原性。示踪分子是通过马钱素的葡萄糖部分的高碘酸盐打开和随后用高比活性的硼酸化钠还原来合成的。兔抗体对马钱素具有高亲和力 (K a = 1.6 × 10 9 1/mol)，并且允许每 0.05 ml 样品检测低至 0.1 ng。该抗血清对马钱素及其苷元具有高度特异性，只有 10-羟基马钱素和 7-表皮马钱素表现出显着的交叉反应性。测试了许多忍冬科细胞培养物将添加的马钱素转化为赛洛加宁的能力。通过标记前体喂养实验，发现威格利亚属、忍冬属、绣球属和红花属的成员打开马钱素的环戊烷环。马钱素生物转化的时间过程使用马钱素和二甲双胍的放射免疫测定法以及作为生物材料的忍冬属植物细胞培养物进行监测。
• Srivastava, Shefali; Raj, Kanwal; Khare, Pratibha, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 2, p. 237 - 247
  作者：Srivastava, Shefali、Raj, Kanwal、Khare, Pratibha、Bhaduri, Amiya P.、Chander, Ramesh、Raghubir, Ram、Mahendra、Rao、Prabhu

  DOI：——

  日期：——
• Raj; Mathad, Vijayavitthal T.; Bhaduri, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 10, p. 1056 - 1061
  作者：Raj、Mathad, Vijayavitthal T.、Bhaduri、Pandey、Patnaik

  DOI：——

  日期：——
• 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.