eunicidiol | 1384270-07-8

• 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: eunicidiol
• 英文别名: (1R,5E,9S)-9-[(2E,4E)-6-hydroxy-6-methylhepta-2,4-dien-2-yl]-6-methyl-2-methylidenecyclodec-5-en-1-ol
• CAS: 1384270-07-8
• 化学式: C₂₀H₃₂O₂
• 分子量: 304.473
• InChiKey: BONUHTOMAPQCIR-NGOVDTHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲醇 、 (R)-(-)-α-甲氧基苯乙酸 、 eunicidiol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 [(1R,5E,9S)-9-[(2E,4E)-6-methoxy-6-methylhepta-2,4-dien-2-yl]-6-methyl-2-methylidenecyclodec-5-en-1-yl] (2R)-2-methoxy-2-phenylacetate
  参考文献：
  名称：

  Eunicidiol, an Anti-inflammatory Dilophol Diterpene from Eunicea fusca

  摘要：

  A new dilophol diterpene, eunicidiol (1), has been isolated from the crude extract of Eunicea fusca, a gorgonian coral collected from Hillsboro Ledge, Florida. This compound was purified, along with fuscol (2) and eunicol (3), using a combination of normal- and reversed-phase chromatography methods. The structure of eunicidiol (1) was elucidated by ID and 2D NMR spectroscopic analysis, and the absolute configuration was assigned using Mosher's method. The anti-inflammatory activity of 1-3 was evaluated by measuring their ability to reduce phorbol myristate acetate (PMA)-induced edema in a mouse ear model. Topical application of a 100 mu g/ear dose of diterpenes 1-3 significantly reduced edema by 44%, 46%, and 54%, respectively. This activity was superior to indomethacin, a known anti-inflammatory used as a control.

  DOI：

  10.1021/np300149y

文献信息

• Eunicidiol, an Anti-inflammatory Dilophol Diterpene from <i>Eunicea fusca</i>
  作者：Douglas H. Marchbank、Fabrice Berrue、Russell G. Kerr

  DOI：10.1021/np300149y

  日期：2012.7.27

  A new dilophol diterpene, eunicidiol (1), has been isolated from the crude extract of Eunicea fusca, a gorgonian coral collected from Hillsboro Ledge, Florida. This compound was purified, along with fuscol (2) and eunicol (3), using a combination of normal- and reversed-phase chromatography methods. The structure of eunicidiol (1) was elucidated by ID and 2D NMR spectroscopic analysis, and the absolute configuration was assigned using Mosher's method. The anti-inflammatory activity of 1-3 was evaluated by measuring their ability to reduce phorbol myristate acetate (PMA)-induced edema in a mouse ear model. Topical application of a 100 mu g/ear dose of diterpenes 1-3 significantly reduced edema by 44%, 46%, and 54%, respectively. This activity was superior to indomethacin, a known anti-inflammatory used as a control.