12,6'-dioctanoyl ginsenoside Rh₂ | 1357259-75-6

• 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: 12,6'-dioctanoyl ginsenoside Rh₂
• 英文别名: 12,6'-Dioctanoyl Ginsenoside Rh2；[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-12-octanoyloxy-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-2-yl]methyl octanoate
• CAS: 1357259-75-6
• 化学式: C₅₂H₉₀O₁₀
• 分子量: 875.281
• InChiKey: KCPBBZLPOURRDV-WCKXOTMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.2
• 重原子数：
  62
• 可旋转键数：
  23
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  人参皂甙 Rh2 、 辛酰氯 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 0.25h， 以48.1%的产率得到12,6'-dioctanoyl ginsenoside Rh₂
  参考文献：
  名称：

  Structural modification of ginsenoside Rh2 by fatty acid esterification and its detoxification property in antitumor

  摘要：

  Ginsenoside Rh-2, one of the most important ginsenosides with anticancer properties in red ginseng, has been developed as principal antitumor ingredient for clinical use. However, the cytotoxicity test in human hepatocyte cell line QSG-7701 (IC50 37.3 mu M) indicated that Rh-2 might show strong cytotoxic side-effect on the normal liver cells. For blunting the toxicity, Rh-2 was structurally modified by reacting with octanoyl chloride to give a dioctanoyl ester of Rh-2 (D-Rh-2) in the present study. MIT assay in QSG-7701 cell line in vitro showed that the cytotoxicity of D-Rh-2 on human hepatocyte cells (IC50 80.5 mu M) was significantly lower than that of Rh-2. While antitumor xenograft assay in mice bearing H22 liver cancer cells in vivo showed that the antitumor activity of D-Rh-2 retained to be strong as that of Rh-2. According to previous pharmacokinetic studies, the fatty acid esterification of Rh-2 might be of detoxification reaction to cells. Additionally, D-Rh-2 showed significant enhancement on increasing thymus index at the dose of 10 mg/kg compared with vehicle treated control group. Thus, D-Rh-2 might indirectly affect tumor growth by stimulating lymphocytes to become cytotoxic to tumor cells. Finally, our findings suggested that D-Rh-2, the fatty acid ester of Rh-2, might attenuate the side-effect by detoxification to human normal cell and could be a more potential candidate for developing as an antitumor drug. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.104

文献信息

• Structural modification of ginsenoside Rh2 by fatty acid esterification and its detoxification property in antitumor
  作者：Gong-Qing Wei、Yi-Nan Zheng、Wei Li、Wen-Cong Liu、Ting Lin、Wei-Yun Zhang、Hai-Feng Chen、Jin-Zhang Zeng、Xiao-Kun Zhang、Quan-Cheng Chen

  DOI：10.1016/j.bmcl.2011.11.104

  日期：2012.1

  Ginsenoside Rh-2, one of the most important ginsenosides with anticancer properties in red ginseng, has been developed as principal antitumor ingredient for clinical use. However, the cytotoxicity test in human hepatocyte cell line QSG-7701 (IC50 37.3 mu M) indicated that Rh-2 might show strong cytotoxic side-effect on the normal liver cells. For blunting the toxicity, Rh-2 was structurally modified by reacting with octanoyl chloride to give a dioctanoyl ester of Rh-2 (D-Rh-2) in the present study. MIT assay in QSG-7701 cell line in vitro showed that the cytotoxicity of D-Rh-2 on human hepatocyte cells (IC50 80.5 mu M) was significantly lower than that of Rh-2. While antitumor xenograft assay in mice bearing H22 liver cancer cells in vivo showed that the antitumor activity of D-Rh-2 retained to be strong as that of Rh-2. According to previous pharmacokinetic studies, the fatty acid esterification of Rh-2 might be of detoxification reaction to cells. Additionally, D-Rh-2 showed significant enhancement on increasing thymus index at the dose of 10 mg/kg compared with vehicle treated control group. Thus, D-Rh-2 might indirectly affect tumor growth by stimulating lymphocytes to become cytotoxic to tumor cells. Finally, our findings suggested that D-Rh-2, the fatty acid ester of Rh-2, might attenuate the side-effect by detoxification to human normal cell and could be a more potential candidate for developing as an antitumor drug. (C) 2011 Elsevier Ltd. All rights reserved.