刺五加苷C3 | 114906-74-0

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 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
• 中文名称: 刺五加苷C3
• 英文名称: ciwujianoside C3
• 英文别名: [(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 114906-74-0
• 化学式: C₅₃H₈₆O₂₁
• 分子量: 1059.25
• InChiKey: XPZZGRWYXQODIS-SEHMIGTGSA-N

物化性质

• 密度：
  1.43±0.1 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  74
• 可旋转键数：
  11
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  334
• 氢给体数：
  12
• 氢受体数：
  21

安全信息

• 储存条件：
  2-8°C

制备方法与用途

生物活性

Ciwujianoside C3 是一种具有口服活性并能穿透血脑屏障的化合物，从刺五加叶子中分离得到。该化合物具有抗炎作用，并可以增强小鼠个体的识别记忆力。

体外研究

• 细胞活力测定

  • 细胞系：RAW 264.7
  • 浓度：10 µM、20 µM 和 40 µM
  • 孵育时间：24 小时
  • 结果：对细胞毒性无影响，抑制 NO 生产

• Western Blot 分析

  • 细胞系：RAW 264.7
  • 浓度：10 µM、20 µM 和 40 µM
  • 孵育时间：24 小时
  • 结果：减少 p-ERK 和 p-JNK 的表达

• RT-PCR

  • 细胞系：RAW 264.7
  • 浓度：10 µM、20 µM 和 40 µM
  • 孵育时间：24 小时
  • 结果：以剂量依赖性方式减少 COX-2 和 iNOS 的 mRNA 表达

体内研究

• 动物模型：小鼠
• 剂量：0.5 mg/kg
• 给药方法：口服；每天 0.5 mg/kg，持续 17 天
• 结果：增强物体识别记忆

化学性质

Ciwujianoside C3 是一种白色结晶粉末，可溶于甲醇、乙醇和 DMSO 等有机溶剂。它来源于刺五加 Acanthopanax senticosus 的干燥根茎。

反应信息

• 作为反应物：
  描述：

  刺五加苷C3 在 mineral acid 作用下， 生成 L-阿拉伯糖 、 L-鼠李糖 、 葡萄糖 、 齐墩果酸
  参考文献：
  名称：

  Shao, Chun-Jie; Kasai, Ryoji; Xu, Jing-Da, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 2, p. 601 - 608

  摘要：

  DOI：
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 以0.42 g的产率得到刺五加苷C3
  参考文献：
  名称：

  Synthesis, biological evaluation and structure-activity relationship studies of hederacolchiside E and its derivatives as potential anti-Alzheimer agents

  摘要：

  Inspired by the previously reported neuroprotective activity of hederacolchiside E (1), we synthesized hederacolchiside E for the first time along with eleven of its derivatives. The neuroprotective effects of these compounds were further evaluated against H2O2- and A beta(1-42)-induced injury using cell-based assays. The derivatives showed obvious differences in activity due to structural variations, and two of them exhibited better neuroprotective effects than 1 in the A beta(1-42)-induced injury model. Compound 7 was the most active derivative and had a relatively simple chemical structure. Moreover, 1 and 7 can significantly reduce the release of lactate dehydrogenase (LDH), level of intracellular reactive oxygen species (ROS) and extent of malondialdehyde (MDA) increase resulting from A beta(1-42) treatment, which demonstrated that these kinds of compounds show neuroprotective effects in Alzheimer's disease (AD) models via modulating oxidative stress. Compound 7 could be used as promising lead for the development of a new type of neuroprotective agent against AD. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.040

文献信息

• First Synthesis of a Bidesmosidic Triterpene Saponin by a Highly Efficient Procedure
  作者：Biao Yu、Jianming Xie、Shaojiang Deng、Yongzheng Hui

  DOI：10.1021/ja9926818

  日期：1999.12.1
• Synthesis, biological evaluation and structure-activity relationship studies of hederacolchiside E and its derivatives as potential anti-Alzheimer agents
  作者：Hui-ning Li、Yang Liu、Zuo-peng Zhang、Zhi-peng Wang、Jing-zheng Hao、Feng-ran Li、Zhan-fang Fan、Li-bo Zou、Mao-sheng Cheng

  DOI：10.1016/j.ejmech.2017.11.040

  日期：2018.1

  Inspired by the previously reported neuroprotective activity of hederacolchiside E (1), we synthesized hederacolchiside E for the first time along with eleven of its derivatives. The neuroprotective effects of these compounds were further evaluated against H2O2- and A beta(1-42)-induced injury using cell-based assays. The derivatives showed obvious differences in activity due to structural variations, and two of them exhibited better neuroprotective effects than 1 in the A beta(1-42)-induced injury model. Compound 7 was the most active derivative and had a relatively simple chemical structure. Moreover, 1 and 7 can significantly reduce the release of lactate dehydrogenase (LDH), level of intracellular reactive oxygen species (ROS) and extent of malondialdehyde (MDA) increase resulting from A beta(1-42) treatment, which demonstrated that these kinds of compounds show neuroprotective effects in Alzheimer's disease (AD) models via modulating oxidative stress. Compound 7 could be used as promising lead for the development of a new type of neuroprotective agent against AD. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Shao, Chun-Jie; Kasai, Ryoji; Xu, Jing-Da, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 2, p. 601 - 608
  作者：Shao, Chun-Jie、Kasai, Ryoji、Xu, Jing-Da、Tanaka, Osamu

  DOI：——

  日期：——