plakilactone E | 1400269-51-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: plakilactone E
• 英文别名: (+)-Plakilactone E；(5R)-3,5-diethyl-5-[(Z,4S)-2-ethyl-4-hydroxyhex-2-enyl]furan-2-one
• CAS: 1400269-51-3
• 化学式: C₁₆H₂₆O₃
• 分子量: 266.381
• InChiKey: MYUFZXOOWWQXMN-SFXKOGKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  plakilactone E 、 甲氧基-三氟甲基苯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 [(Z,3S)-5-[[(2R)-2,4-diethyl-5-oxofuran-2-yl]methyl]hept-4-en-3-yl] (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Plakilactones from the Marine Sponge Plakinastrella mamillaris. Discovery of a New Class of Marine Ligands of Peroxisome Proliferator-Activated Receptor γ

  摘要：

  In this paper we report the isolation and the molecular characterization of a new class of PPAR gamma ligands from the marine environment. Biochemical characterization of a library of 13 oxygenated polyketides isolated from the marine sponge Plakinastrella mamillaris allowed the discovery of gracilioether B and plakilactone C as selective PPAR gamma ligands in transactivation assays. Both agents covalently bind to the PPAR gamma ligand binding domain through a Michael addition reaction involving a protein cysteine residue and the alpha,beta-unsaturated ketone in their side chains. Additionally, gracilioether C is a noncovalent agonist for PPAR gamma, and methyl esters 1 and 2 are noncovalent antagonists. Structural requirements for the interaction of these agents within the PPAR gamma ligand binding domain were obtained by docking analysis. Gracilioether B and plakilactone C regulate the expression of PPAR gamma-dependent genes in the liver and inhibit the generation of inflammatory mediators by macrophages.

  DOI：

  10.1021/jm300911g