2β-hydroxycurcumalactone | 1552288-10-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2β-hydroxycurcumalactone
• CAS: 1552288-10-4
• 化学式: C₁₅H₂₄O₃
• 分子量: 252.354
• InChiKey: CXINIQFJWBUNER-RLPMIEJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  curdione 在 盐酸 作用下， 以 甲醇 、 aq. phosphate buffer 、 水 为溶剂， 反应 76.0h， 生成 2β-hydroxycurcumalactone
  参考文献：
  名称：

  “Mirror-Image” Manipulation of Curdione Stereoisomer Scaffolds by Chemical and Biological Approaches: Development of a Sesquiterpenoid Library

  摘要：

  The sesquiterpenoid curdione is one of the main bioactive components in the essential oil of Rhizoma Curcumae (Curcuma wenyujin, Curcuma phaeocaulis, and Curcuma kwangsiensis), which has been clinically used for the treatment of cancer in mainland China. Recently it was reported that natural curdione could be hydroxylated by Aspergillus niger and transferred to its corresponding curcumalactones under acidic conditions. Based on this study, the development of a sesquiterpenoid library through the "mirror-image" manipulation of bioactive (non)natural curdione scaffolds by chemical and biological approaches is presented herein. A. niger induced the hydroxylation of two pairs of curdione enantiomers, yielding the corresponding mirror-image hydroxylated curdiones. Simultaneously, the acid-mediated intramolecular "ene" rearrangements of these curdiones and hydroxylated curdione enantiomers yielded the corresponding mirror-image curcumalactones and hydroxylated curcumalactones. Among the 16 pairs of enantiomers obtained in this study, 23 compounds are new sesquiterpenoids. These curdione and curcumalactone derivatives are of particular interest, as they have the potential to be used as lead compounds and scaffolds in drug discovery.

  DOI：

  10.1021/np500864e

文献信息

• An insight into the curdione biotransformation pathway by <i>Aspergillus niger</i>
  作者：Yinan Chen、Lang Zhang、Bin Qin、Xin Zhang、Xian Jia、Xiaoying Wang、Danni Jin、Song You

  DOI：10.1080/14786419.2013.873434

  日期：2014.4.3

  Curdione (1), a sesquiterpene with a germacrane skeleton from rhizomes of Curcuma wenyujin, has attracted attention due to its important pharmacological properties. Herein, we investigated the chemo-biotransformation of curdione (1) systematically using Aspergillus niger AS 3.739. Regio- and stereoselective hydroxylation of curdione with filamentous fungus A. niger AS 3.739 led to seven metabolites including four new compounds 3-hydroxycurcumalactone, 2-hydroxycurcumalactone, (10S)-9,10-dihydroxy-curcumalactone and (10R)-9,10-dihydroxy-curcumalactone. Their structures were determined by spectroscopic techniques including two-dimensional NMR and TOF-MS (Time of Flight Mass Spectrometry). Based upon the analysis of biological and chemical conversions of curdione, a tentative metabolic pathway via chemo-bio cascade reactions is proposed in A. niger system, which provides an insight into the corresponding metabolism of curdione in animal systems. In addition, experiments with selected monooxygenase inhibitors suggest that cytochrome P450 monooxygenase played a crucial role in the hydroxylation of curdione.
• “Mirror-Image” Manipulation of Curdione Stereoisomer Scaffolds by Chemical and Biological Approaches: Development of a Sesquiterpenoid Library
  作者：Bin Qin、Yuxin Li、Lingxin Meng、Jingping Ouyang、Danni Jin、Lei Wu、Xin Zhang、Xian Jia、Song You

  DOI：10.1021/np500864e

  日期：2015.2.27

  The sesquiterpenoid curdione is one of the main bioactive components in the essential oil of Rhizoma Curcumae (Curcuma wenyujin, Curcuma phaeocaulis, and Curcuma kwangsiensis), which has been clinically used for the treatment of cancer in mainland China. Recently it was reported that natural curdione could be hydroxylated by Aspergillus niger and transferred to its corresponding curcumalactones under acidic conditions. Based on this study, the development of a sesquiterpenoid library through the "mirror-image" manipulation of bioactive (non)natural curdione scaffolds by chemical and biological approaches is presented herein. A. niger induced the hydroxylation of two pairs of curdione enantiomers, yielding the corresponding mirror-image hydroxylated curdiones. Simultaneously, the acid-mediated intramolecular "ene" rearrangements of these curdiones and hydroxylated curdione enantiomers yielded the corresponding mirror-image curcumalactones and hydroxylated curcumalactones. Among the 16 pairs of enantiomers obtained in this study, 23 compounds are new sesquiterpenoids. These curdione and curcumalactone derivatives are of particular interest, as they have the potential to be used as lead compounds and scaffolds in drug discovery.