3α-(uracil-1-yl)-2,3-dihydrowithaferin A

• 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: 3α-(uracil-1-yl)-2,3-dihydrowithaferin A
• 英文别名: 1-[(1S,2R,5R,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-5-yl]pyrimidine-2,4-dione
• 化学式: C₃₂H₄₂N₂O₈
• 分子量: 582.694
• InChiKey: NQVNBCSTEGPDTK-OPMYPFGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  42
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  尿嘧啶 、 醉茄素 A 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以1.5 mg的产率得到3α-(uracil-1-yl)-2,3-dihydrowithaferin A
  参考文献：
  名称：

  Unusual withanolides from aeroponically grown Withania somnifera

  摘要：

  In an attempt to maximize production and the structural diversity of plant metabolites, the effect of growing the medicinal plant Withania somnifera under soil-less aeroponic conditions on its ability to produce withaferin A and withanolides was investigated. It resulted in the isolation and characterization of two compounds, 3 alpha-(uracil-1-yl)-2,3-dihydrowithaferin A (1) and 3 beta-(adenin-9-yl)-2,3-dihydrowithaferin A (2), in addition to 10 known withanolides including 2,3-dihydrowithaferin A-3 beta-O-sulfate. 3 beta-O-Butyl-2,3-dihydrowithaferin A (3), presumably an artifact formed from withaferin A during the isolation process was also encountered. Reaction of withaferin A with uracil afforded 1 and its epimer, 3 beta-(uracil-1-yl)-2,3-dihydrowithaferin A (4). The structures of these compounds were elucidated on the basis of their high resolution mass and NMR spectroscopic data. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2010.12.020

文献信息

• Unusual withanolides from aeroponically grown Withania somnifera
  作者：Ya-ming Xu、Song Gao、Daniel P. Bunting、A.A. Leslie Gunatilaka

  DOI：10.1016/j.phytochem.2010.12.020

  日期：2011.4

  In an attempt to maximize production and the structural diversity of plant metabolites, the effect of growing the medicinal plant Withania somnifera under soil-less aeroponic conditions on its ability to produce withaferin A and withanolides was investigated. It resulted in the isolation and characterization of two compounds, 3 alpha-(uracil-1-yl)-2,3-dihydrowithaferin A (1) and 3 beta-(adenin-9-yl)-2,3-dihydrowithaferin A (2), in addition to 10 known withanolides including 2,3-dihydrowithaferin A-3 beta-O-sulfate. 3 beta-O-Butyl-2,3-dihydrowithaferin A (3), presumably an artifact formed from withaferin A during the isolation process was also encountered. Reaction of withaferin A with uracil afforded 1 and its epimer, 3 beta-(uracil-1-yl)-2,3-dihydrowithaferin A (4). The structures of these compounds were elucidated on the basis of their high resolution mass and NMR spectroscopic data. (C) 2011 Elsevier Ltd. All rights reserved.