新莪术二酮 | 108944-67-8

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 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
• 中文名称: 新莪术二酮
• 英文名称: neocurdione
• 英文别名: (3R,6E,10S)-6,10-dimethyl-3-propan-2-ylcyclodec-6-ene-1,4-dione
• CAS: 108944-67-8
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: KDPFMRXIVDLQKX-OAIDTJHVSA-N

物化性质

• 沸点：
  347.6±42.0 °C(Predicted)
• 密度：
  0.931±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 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：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 安全说明：
  SA

制备方法与用途

生物活性方面，Neocurdione 是一种具有肝保护作用的倍半萜，它来源于 Curcuma zedoaria 的根茎。研究显示，Neocurdione 能有效地缓解 D-半乳糖胺 (D-Gain) 和脂多糖 (LPS) 诱导的小鼠急性肝损伤。

反应信息

• 作为反应物：
  描述：

  新莪术二酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成
  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