michampanolide

• 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: michampanolide
• 英文别名: (-)-(3aS,6R,6aR,8aR,9S,9aS)-decahydro-6,9-dihydroxy-6,8a-dimethyl-3-methylenecyclobuta[6,7]cycloocta[1,2-b]furan-2(3H)-one；(1S,2S,3R,6R,7R,10S)-2,7-dihydroxy-3,7-dimethyl-11-methylidene-13-oxatricyclo[8.3.0.03,6]tridecan-12-one
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: BIURAVISNLIZHC-NMAMFNKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  parthenolide 在 amberlyst 15 作用下， 以 水 、 丙酮 为溶剂， 反应 72.0h， 以4.3 mg的产率得到michampanolide
  参考文献：
  名称：

  Inhibition of NF-kB and metalloproteinase-9 expression and secretion by parthenolide derivatives

  摘要：

  Semisynthetic derivatives of parthenolide (1) were tested on NF-kappa B driven transcription and metalloproteinase-9 (MMP-9) expression and secretion. The four membered ring compounds 5 and 6, obtained by acidic treatment of 1, exhibited a higher activity with respect to 1 in all the biological assays. Then an increased ability of the 5 and 6 to inhibit NF-kappa B driven transcription may lead to a down-regulation of MMP-9 expression and secretion. This work provides new details about the structural requisites for NF-kappa B inhibition. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.080

文献信息

• Sesquiterpene lactones from Michelia champaca
  作者：Ulla Jacobsson、Vijaya Kumar、Shantini Saminathan

  DOI：10.1016/0031-9422(94)00972-v

  日期：1995.7

  Five sesquiterpene lactones were isolated from Michelia champaca root bark. One of these, michampanolide (2,7-dihydroxy-3,7-dimethyl-11-methylene-13-oxatricyclo[8,3,0,0,3,b]tridecan-12-one), possessed a new skeleton, while two others, 8-acetoxyparthenolide and magnograndiolide, were isolated for the first time from M. champaca.

  五种倍半萜内酯是从含笑根皮中分离出来的。其中之一，michampanolide（2,7-dihydroxy-3,7-dimethyl-11-methylene-13-oxatricyclo[8,3,0,0,3,b]tridecan-12-one），拥有一个新的骨架，而另外两种，8-乙酰氧基小白菊内酯和 magnograndiolide，则是首次从 M. champaca 中分离出来。
• Inhibition of NF-kB and metalloproteinase-9 expression and secretion by parthenolide derivatives
  作者：Mario Dell’Agli、Germana V. Galli、Enrica Bosisio、Michele D’Ambrosio

  DOI：10.1016/j.bmcl.2009.02.080

  日期：2009.4

  Semisynthetic derivatives of parthenolide (1) were tested on NF-kappa B driven transcription and metalloproteinase-9 (MMP-9) expression and secretion. The four membered ring compounds 5 and 6, obtained by acidic treatment of 1, exhibited a higher activity with respect to 1 in all the biological assays. Then an increased ability of the 5 and 6 to inhibit NF-kappa B driven transcription may lead to a down-regulation of MMP-9 expression and secretion. This work provides new details about the structural requisites for NF-kappa B inhibition. (C) 2009 Elsevier Ltd. All rights reserved.