1β-acetoxy-9α-cinnamoyloxy-β-dihydroagarofuran | 133462-17-6

• 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: 1β-acetoxy-9α-cinnamoyloxy-β-dihydroagarofuran
• 英文别名: [(1S,2R,5S,6S,7S,9R)-5-acetyloxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.01,6]dodecan-7-yl] 3-phenylprop-2-enoate
• CAS: 133462-17-6
• 化学式: C₂₆H₃₄O₅
• 分子量: 426.553
• InChiKey: DQWLBHRONRCNFM-HGMJEISVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1β-acetoxy-9α-cinnamoyloxy-β-dihydroagarofuran 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以83%的产率得到(1S,2R,5S,6S,7S,9R)-2,6,10,10-Tetramethyl-11-oxa-tricyclo[7.2.1.0^1,6]dodecane-5,7-diol
  参考文献：
  名称：

  来自 Celastrus gemmatus 的倍半萜类化合物

  摘要：

  三种新的倍半萜类化合物 1-β,6-α,8-α-triacetoxy-9-β-benzoyloxy-β-dihydroagarofuran, 8-beta-acetoxy-1-beta,9-beta-dibenzoyloxy-6-alpha-hydroxy-beta -dihydroagarofuran 和 1-beta-acetoxy-9-alpha-cinnamoyloxy-beta-dihydroagarofuran, 和一种已知的倍半萜类 9-alpha-acetoxy-1-beta,6-alpha-dibenzoyloxy-beta-dihydroagarofuran 从 Celastrus gemmatus 及其结构中分离出来通过光谱和化学研究确定。

  DOI：

  10.1016/0031-9422(91)84136-g

文献信息

• Natural β-Dihydroagarofuran-Type Sesquiterpenoids as Cognition-Enhancing and Neuroprotective Agents from Medicinal Plants of the Genus <i>Celastrus</i>
  作者：Ruonan Ning、Yun Lei、Shuangzhu Liu、Huan Wang、Rujun Zhang、Wei Wang、Yingdong Zhu、Haiyan Zhang、Weimin Zhao

  DOI：10.1021/acs.jnatprod.5b00234

  日期：2015.9.25

  Alzheimer's disease (AD) is an irreversible, multifaceted, and progressive neurodegenerative disorder. Over the past 30 years, the search for anti-AD drugs has been primarily based on the cholinergic deficiency hypothesis and/or the beta-amyloid (A beta) cascade hypothesis. In this study, we report the identification of 16 new and 38 known beta-dihydroagarofuran-type sesquiterpenoids from Celastrus flagellaris and Celastrus angulatus. The beta-dihydroagarofuran-type sesquiterpenoids 58, 59, 61, and 63 significantly attenuated scopolamine-induced prolonged escape latency and increased number of errors compared with the control group. At 10 mu M, 21 of the 62 tested beta-dihydroagarofuran-type sesquiterpenoids rescued A beta(25-35)-induced SH-SY5Y cells from viability reduction, which increased the cell viability from 64.6% for the model to more than 74.0%. The majority of the beta-dihydroagarofuran-type sesquiterpenoids with ester groups exhibited stronger activity than those with free hydroxy groups or without substituents at the same positions. These results identified a new chemical skeleton as drug lead for the investigation of novel therapeutic agents against AD.