rhoipteleanin A

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: rhoipteleanin A
• 英文别名: [(1R,2S,19R,20S,22R)-7,8,9,12,13,14,28,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.02,19.05,10.011,16.026,31.032,37]nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaen-20-yl] 2-[(1R,2S,19R,20S,22R)-7,8,9,12,13,14,28,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-20-(3,4,5-trihydroxybenzoyl)oxy-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.02,19.05,10.011,16.026,31.032,37]nonatriaconta-5,7,9,11(16),12,14,26,28,30,32,34,36-dodecaen-15-yl]-3,4,5-trihydroxybenzoate
• 化学式: C₈₂H₅₄O₅₂
• 分子量: 1871.3
• InChiKey: YQXGMCISEUTANJ-ZHJPOWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  134
• 可旋转键数：
  7
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  888
• 氢给体数：
  30
• 氢受体数：
  52

反应信息

• 作为反应物：
  描述：

  硫酸二甲酯 、 rhoipteleanin A 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以52 mg的产率得到
  参考文献：
  名称：

  Structures and Biogenesis of Rhoipteleanins, Ellagitannins Formed by Stereospecific Intermolecular C-C Oxidative Coupling, Isolated from Rhoiptelea chiliantha

  摘要：

  Seven novel ellagitannins named rhoipteleanin A-G were isolated from the fruits of Rhoiptelea chiliantha and their structures were unequivocally established on the basis of spectroscopic and chemical evidence. In the molecules of rhoipteleanin A-F, (S, S)-flavogallonyl esters spanned two glucopyranose moieties; hence, these tannins represent the first dimeric ellagitannins generated by stereospecific intermolecular C-C oxidative coupling between the galloyl and hexahydroxydiphenoyl groups. The change in the 1H-NMR chemical shifts of specific proton signals of 1(β)-O-galloylpedunculagin, the biogenetic precursor of rhoipteleanin A, in dueterium oxide at various concentrations suggested that the stereochemically regulated hydrophobic interaction between two molecules of the precursor restricts the intermolecular C-C coupling to S-biphenyl bond formation.

  DOI：

  10.1248/cpb.45.1915

文献信息

• Rhoipteleanins A and E, dimeric ellagitannins formed by intermolecular C–C oxidative coupling from Rhoiptelea chiliantha
  作者：Zhi-Hong Jiang、Takashi Tanaka、Isao Kouno

  DOI：10.1039/c39950001467

  日期：——

  The first dimeric ellagitannins, rhoipteleanins A and E, generated biogenetically by intermolecular C–C oxidative coupling, are isolated from the fruits of Rhoiptelea chiliantha and structurally elucidated on the basis of spectroscopic and chemical evidence.

  第一个二聚体椰油单宁，rhoipteleanins A和E，通过分子间C－C氧化偶联在生物上合成，从Rhoiptelea chiliantha的果实中分离，并基于光谱和化学证据对其结构进行了阐明。
• Structures and Biogenesis of Rhoipteleanins, Ellagitannins Formed by Stereospecific Intermolecular C-C Oxidative Coupling, Isolated from Rhoiptelea chiliantha
  作者：Takashi TANAKA、Zhi-Hong JIANG、Isao KOUNO

  DOI：10.1248/cpb.45.1915

  日期：——

  Seven novel ellagitannins named rhoipteleanin A-G were isolated from the fruits of Rhoiptelea chiliantha and their structures were unequivocally established on the basis of spectroscopic and chemical evidence. In the molecules of rhoipteleanin A-F, (S, S)-flavogallonyl esters spanned two glucopyranose moieties; hence, these tannins represent the first dimeric ellagitannins generated by stereospecific intermolecular C-C oxidative coupling between the galloyl and hexahydroxydiphenoyl groups. The change in the 1H-NMR chemical shifts of specific proton signals of 1(β)-O-galloylpedunculagin, the biogenetic precursor of rhoipteleanin A, in dueterium oxide at various concentrations suggested that the stereochemically regulated hydrophobic interaction between two molecules of the precursor restricts the intermolecular C-C coupling to S-biphenyl bond formation.