[(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] octanoate

• 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] octanoate
• 化学式: C₂₈H₄₂O₇
• 分子量: 490.637
• InChiKey: BEDCQCIXBARHDY-IURPHOMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  冬凌草甲素 、 辛酸 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38%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] octanoate
  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

• Probing the Anticancer Action of Oridonin with Fluorescent Analogues: Visualizing Subcellular Localization to Mitochondria
  作者：Shengtao Xu、Shanshan Luo、Hong Yao、Hao Cai、Xiaoming Miao、Fang Wu、Dong-Hua Yang、Xiaoming Wu、Weijia Xie、Hequan Yao、Zhe-Sheng Chen、Jinyi Xu

  DOI：10.1021/acs.jmedchem.6b00408

  日期：2016.5.26

  Oridonin (1) is a complex ent-kaurane diterpenoid exhibiting remarkable antitumor activity. However, the detailed mechanism or cellular target that underlies this activity has not yet been identified. Herein, we report an efficient approach for exploring the anticancer mechanism of oridonin through development of the potent fluorescent analogues. A series of novel fluorescent oridonin probes linked with coumarin moieties were designed, synthesized, and characterized. Fluorescence microscopy and confocal imaging studies suggested that fluorescent oridonin probe 17d was rapidly taken up into tumor cells and the mitochondrion was the main site of its accumulation. Moreover, we confirmed that cytochrome c played an important role in oridonin induced mitochondrion-mediated apoptosis and alpha,beta-unsaturated ketone is the active moiety of oridonin, which is crucial to its uptake, localization, and cytotoxicity. Our results provide new insights on the molecular mechanism of oridonin and would be useful for its further development into an antitumor agent.