(2R)-2-hydroxycurdione | 139416-58-3

• 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: (2R)-2-hydroxycurdione
• 英文别名: 2β-hydroxycurdione；(2R)-2β-hydroxycurdione；(3S,6E,8R,10S)-8-hydroxy-6,10-dimethyl-3-propan-2-ylcyclodec-6-ene-1,4-dione
• CAS: 139416-58-3
• 化学式: C₁₅H₂₄O₃
• 分子量: 252.354
• InChiKey: WLHCFOUGUVMPPJ-JOSBEWLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-2-hydroxycurdione 在 Aspergillus niger 作用下， 反应 24.0h， 以4 mg的产率得到2β-hydroxycurcumalactone
  参考文献：
  名称：

  An insight into the curdione biotransformation pathway by Aspergillus niger

  摘要：

  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.

  DOI：

  10.1080/14786419.2013.873434
• 作为产物：
  描述：

  curdione 在 Aspergillus niger AS 3.739 作用下， 反应 48.0h， 生成 3α-hydroxycurdione 、 (2R)-2-hydroxycurdione
  参考文献：
  名称：

  An insight into the curdione biotransformation pathway by Aspergillus niger

  摘要：

  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.

  DOI：

  10.1080/14786419.2013.873434

文献信息

• Structural determination of three new germacrane-type sesquiterpene alcohols from curdione by microbial transformation
  作者：Xiao-chi Ma、Jian Zheng、Li-jun Wu、De-an Guo

  DOI：10.1002/mrc.1922

  日期：2007.1

  Five germacrane‐type sesquiterpene alcohols obtained from curdione (1) by microbial biotransformation were isolated. Their structures were characterized as (2R)‐2β‐hydroxycurdione (2), 1α, 10β‐epoxy‐11‐hydroxycurdione (3), (2S)‐2α, 11‐dihydroxycurdione (4), 11,15‐dihydroxycurdione (5) and (3R)‐3α‐hydroxycurdione (6) based on the extensive NMR studies. Among them, 4, 5 and 6 are new compounds. Copyright

  通过微生物生物转化从凝乳酮 (1) 中分离出五种锗烷型倍半萜醇。它们的结构表征为 (2R)-2β-羟基脲 (2), 1α, 10β-环氧-11-羟基脲 (3), (2S)-2α, 11-二羟基脲 (4), 11,15-二羟基脲 (5)和 (3R)-3α-羟基脲 (6) 基于广泛的 NMR 研究。其中4、5、6为新化合物。版权所有 © 2007 John Wiley & Sons, Ltd.
• “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.
• Biotransformation of the germacrane type sesquiterpene curdione by suspension cultured cells of Lonicera japonica
  作者：Takeshi Horiike、Masaaki Ohshiro、Masanori Kuroyanagi

  DOI：10.1016/s0031-9422(96)00569-9

  日期：1997.2

  Curdione, a sesquiterpene with a germacrane skeleton, was incubated with suspension cultured cells induced from calli of Lonicera japonica for 10 days. The ethyl acetate-soluble fraction of the culture medium gave a number of products, of which six were shown to be (2S)-2-hydroxycurdione, (2R)-2-hydroxycurdione, (8S)-6-hydroxycurdione, (2R, 8S)-8-hydro-2-hydroxycurdione, (1S, 10S)-1,10-epoxycurdione and (1R, 10R)-1.10-epoxycurdione, respectively. Copyright (C) 1997 Elsevier Science Ltd.
• 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.