sinularolide E | 852469-28-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: sinularolide E
• 英文别名: (1aR,4E,8E,10R,10aR,13aR,14aR)-2,3,6,7,10,10a,13,13a,14,14a-decahydro-10-hydroxy-1a,5,9-trimethyl-13-methylideneoxireno[4,5]cyclotetradeca[1,2-b]furan-12(1aH)-one；(1R,3R,4R,13R,14R,7E,11E)-13-hydroxy-3,4-epoxycembra-7,11,15(17)-trien-16,14-olide；lobophytolide D；durumolide J；(1R,3R,5R,8E,12E,14R,15R)-14-hydroxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.03,5]octadeca-8,12-dien-17-one
• CAS: 852469-28-4
• 化学式: C₂₀H₂₈O₄
• 分子量: 332.44
• InChiKey: HVJGVUTXXJGUKC-CZAZWBCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  sinularolide E 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 吡啶 作用下， 以0.4 mg的产率得到
  参考文献：
  名称：

  Anti-inflammatory cembranolides from the soft coral Lobophytum durum

  摘要：

  Chemical investigation of the soft coral Lobophytum durum resulted in the isolation of seven new cembranolides, durumolides F-L (1-7), as well as one previously characterized cembranolides, sinularolide D (8). The molecular structures of these isolated metabolites were determined mainly through NMR techniques and HRESIMS analysis. Moreover, the absolute configurations of 1 and 5 were established by application of modified Mosher's method. The antibacterial activities, anti-inflammatory effects, and anti-HCMV (Human cytomegalovirus) endonuclease activity of metabolites 1-8 were also evaluated in vitro. Anti-inflammatory activity of metabolites 1 and 6 (10 mu M) significantly reduced the levels of the iNOS protein to 0.8 +/- 0.6% and 5.7 +/- 2.2%, respectively, and COX-2 protein to 47.8 +/- 9.0% and 71.6 +/- 5.8%, respectively. Metabolites 1-8 (100 mu g/disk) exhibited weak antibacterial activity against Salmonella enteritidis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.053