daturolactone 1 | 41093-93-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: daturolactone 1
• 英文别名: daturalactone；(1S,2S,4S,5R,10R,11S,13S,14R,15R,18S)-15-[(1S)-1-[(1S,4R,6S)-1,6-dimethyl-2-oxo-3,7-dioxabicyclo[4.1.0]heptan-4-yl]ethyl]-5,13-dihydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one
• CAS: 41093-93-0
• 化学式: C₂₈H₃₈O₇
• 分子量: 486.606
• InChiKey: UZLXIIADBIXQHY-JNUSPZCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (1S,4R,6S)-1,6-dimethyl-4-[(1S)-1-[(1S,2S,4S,5R,9R,10S,11S,13S,14R,15R,18S)-5,9,13-trihydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-15-yl]ethyl]-3,7-dioxabicyclo[4.1.0]heptan-2-one 在 Jones reagent 作用下， 以 丙酮 为溶剂， 生成 daturolactone 1
  参考文献：
  名称：

  Isolation, characterization and biological evaluation of datura lactones as potential immunomodulators

  摘要：

  Phytochemical investigation of Datura quercifolia (Solanaceae) plant yielded a new datura lactone, 1 beta,5 alpha,12 alpha-trihydroxy-6 alpha,7 alpha,24 alpha,25 alpha-diepoxy-20S,22R with-2-enolide (1), along with two known compounds, 2 and 3. The structure of I was established on the basis of spectral analysis, as well as by its chemical transformation into known datura lactones. These compounds have been evaluated for immunomodulatory activity by observing their effect on antibody production, T-cell and B-cell activation, and cytokine production from splenocytes. Compound 2 was found to be the most promising immunostimulator in the present study. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.040

文献信息

• Isolation, characterization and biological evaluation of datura lactones as potential immunomodulators
  作者：B.A. Bhat、K.L. Dhar、S.C. Puri、M.A. Qurishi、A. Khajuria、Amit Gupta、G.N. Qazi

  DOI：10.1016/j.bmc.2005.07.040

  日期：2005.12

  Phytochemical investigation of Datura quercifolia (Solanaceae) plant yielded a new datura lactone, 1 beta,5 alpha,12 alpha-trihydroxy-6 alpha,7 alpha,24 alpha,25 alpha-diepoxy-20S,22R with-2-enolide (1), along with two known compounds, 2 and 3. The structure of I was established on the basis of spectral analysis, as well as by its chemical transformation into known datura lactones. These compounds have been evaluated for immunomodulatory activity by observing their effect on antibody production, T-cell and B-cell activation, and cytokine production from splenocytes. Compound 2 was found to be the most promising immunostimulator in the present study. (c) 2005 Elsevier Ltd. All rights reserved.