[(1S,2S,5S,8R,9S,10S,11R,15S,18R)-9,10,15-trihydroxy-12,12-dimethyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.15,8.01,11.02,8]octadecan-18-yl] 4-(trifluoromethyl)benzoate

• 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: [(1S,2S,5S,8R,9S,10S,11R,15S,18R)-9,10,15-trihydroxy-12,12-dimethyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.15,8.01,11.02,8]octadecan-18-yl] 4-(trifluoromethyl)benzoate
• 化学式: C₂₈H₃₁F₃O₇
• 分子量: 536.545
• InChiKey: RZSFIBKLMJMQLJ-ULLBHDERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  38
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  冬凌草甲素 、 4-三氟甲基苯甲酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以22%的产率得到[(1S,2S,5S,8R,9S,10S,11R,15S,18R)-9,10,15-trihydroxy-12,12-dimethyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.15,8.01,11.02,8]octadecan-18-yl] 4-(trifluoromethyl)benzoate
  参考文献：
  名称：

  Antitumor and Antibacterial Derivatives of Oridonin: A Main Composition of Dong-Ling-Cao

  摘要：

  赤芝（Isodon rubescens）作为传统的绿茶已有1000多年的历史，其许多药用功能也非常有用，例如其著名的抗肿瘤和抗菌活性。oridonin是从这种药用茶中提取的生物活性ent-kaurane二萜，是其主要成分。在此，设计并合成了22种新型oridonin衍生物，并首次评估了它们的抗菌活性。其中，化合物12对枯草芽孢杆菌的MIC值为2.0 μg/mL，比阳性对照氯霉素强近3倍，最具潜力。还测试了其抗增殖特性，化合物19的活性比紫杉醇更强。首次揭示了19在CaEs-17癌细胞中的凋亡诱导能力、细胞周期的S期阻滞效应和线粒体膜电位的影响。基于上述结果，化合物19在CaEs-17细胞中诱导的细胞凋亡很可能是通过内源性凋亡途径实现的。

  DOI：

  10.3390/molecules21050575

文献信息

• Antitumor and Antibacterial Derivatives of Oridonin: A Main Composition of Dong-Ling-Cao
  作者：Dahong Li、Tong Han、Shengtao Xu、Tingting Zhou、Kangtao Tian、Xu Hu、Keguang Cheng、Zhanlin Li、Huiming Hua、Jinyi Xu

  DOI：10.3390/molecules21050575

  日期：——

  Isodon rubescens has been used as a traditional green tea for more than 1000 years and many medicinal functions of I. rubescens are also very useful, such as its well-known antitumor and antibacterial activities. Oridonin, a bioactive ent-kaurane diterpenoid, is the major ingredient of this medicinal tea. Herein, 22 novel oridonin derivatives were designed and synthesized. The antibacterial activity was evaluated for the first time. Compound 12 was the most promising one with MIC of 2.0 μg/mL against B. subtilis, which was nearly 3-fold stronger than positive control chloromycetin. The antiproliferative property was also assayed and compound 19 showed stronger activity than taxol. The apoptosis-inducing ability, cell cycle arrest effect at S phase and influence of mitochondrial membrane potential by 19 in CaEs-17 cancer cells were first disclosed. Based on the above results, the cell apoptosis induced by compound 19 in CaEs-17 cells was most probably involved in the intrinsic apoptotic pathway.

  赤芝（Isodon rubescens）作为传统的绿茶已有1000多年的历史，其许多药用功能也非常有用，例如其著名的抗肿瘤和抗菌活性。oridonin是从这种药用茶中提取的生物活性ent-kaurane二萜，是其主要成分。在此，设计并合成了22种新型oridonin衍生物，并首次评估了它们的抗菌活性。其中，化合物12对枯草芽孢杆菌的MIC值为2.0 μg/mL，比阳性对照氯霉素强近3倍，最具潜力。还测试了其抗增殖特性，化合物19的活性比紫杉醇更强。首次揭示了19在CaEs-17癌细胞中的凋亡诱导能力、细胞周期的S期阻滞效应和线粒体膜电位的影响。基于上述结果，化合物19在CaEs-17细胞中诱导的细胞凋亡很可能是通过内源性凋亡途径实现的。