orientin-2''-O-galactopyranoside | 1377947-82-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: orientin-2''-O-galactopyranoside
• 英文别名: 2′’-O-β-L-galactopyranosylorientin；2''-O-Beta-L-Galorientin；8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
• CAS: 1377947-82-4
• 化学式: C₂₇H₃₀O₁₆
• 分子量: 610.526
• InChiKey: QQBFHNKJGBCSLG-AMBXKRCHSA-N

物化性质

• 沸点：
  988.9±65.0 °C(Predicted)
• 密度：
  1.87±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  43
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  277
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  orientin-2''-O-galactopyranoside 在 盐酸 、 水 作用下， 反应 4.0h， 生成 荭草苷
  参考文献：
  名称：

  Controlled acid hydrolysis and kinetics of flavone C-glycosides from trollflowers

  摘要：

  Acid hydrolysis mechanisms of orientin-2 ''-O-galactopyranoside (OGA), orientin and other flavone C-glycosides in the trollflowers (Trollius chinensis Bunge) were studied in this report for the first time. Hydrolysis parameters including temperature, acidity, solvent and reaction time were comprehensively investigated. OGA could be hydrolyzed to orientin, followed by an isomerization to isoorientin via a reversible Wessely-Moser rearrangement reaction under stronger acidic conditions. A first-order kinetic model fitted the hydrolysis process of OGA well. Under the optimal hydrolysis conditions of 80 degrees C, 1.0 mol/L H+ and 7 h reaction time, about 77% OGA was transformed to orientin with no detectable isoorientin. These results could be helpful for better understanding of the acid hydrolysis kinetics of flavone C-glycosides, as well as the preparation of these valuable components under controlled acid hydrolysis conditions. (C) 2014 Jiang-Yun Liu. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.11.021
• 作为产物：
  描述：

  6'''-(3-hydroxy-3-methylglutaroyl)-2''-O-β-D-galactopyranosyl orientin 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 orientin-2''-O-galactopyranoside 、 荭草苷
  参考文献：
  名称：

  FlavoneC-glycosides from the flowers ofTrollius chinensisand their anti-complementary activity

  摘要：

  Phytochemical investigation of ethanol extract from the flowers of Trollius chinensis Bunge resulted in the isolation of two new flavone C-glycosides (12), along with 10 known compounds (312). The structures of the new compounds were established as 6?-(3-hydroxy-3-methylglutaroyl)-2-O--d-galactopyranosyl orientin (1) and 6?-(3-hydroxy-3-methylglutaroyl)-2-O--d-galactopyranosyl vitexin (2) on the basis of various spectroscopic analysis (including different 1D and 2D NMR spectroscopies, high-resolution electrospray ionization mass spectrometry) and chemical evidences. Bioassay showed that eight flavonoids inhibited complement activation on the classic pathway in vitro, with their IC50 values ranging from 0.88 to 4.02mM, which may contribute to the applications of the herb in treatment of acute respiratory distress syndrome, etc.

  DOI：

  10.1080/10286020.2012.760545

文献信息

• Characterization of a Highly Selective 2″-<i>O</i>-Galactosyltransferase from <i>Trollius chinensis</i> and Structure-Guided Engineering for Improving UDP-Glucose Selectivity
  作者：Shuang Liu、Meng Zhang、Yangoujie Bao、Kuan Chen、Lulu Xu、Huifei Su、Yi Kuang、Zilong Wang、Xue Qiao、Min Ye

  DOI：10.1021/acs.orglett.1c02581

  日期：2021.12.3
• Flavone<i>C</i>-glycosides from the flowers of<i>Trollius chinensis</i>and their anti-complementary activity
  作者：Jiang-Yun Liu、Sheng-Yin Li、Jian-Yong Feng、Yan Sun、Jin-Na Cai、Xiao-Fei Sun、Shi-Lin Yang

  DOI：10.1080/10286020.2012.760545

  日期：2013.4

  Phytochemical investigation of ethanol extract from the flowers of Trollius chinensis Bunge resulted in the isolation of two new flavone C-glycosides (12), along with 10 known compounds (312). The structures of the new compounds were established as 6?-(3-hydroxy-3-methylglutaroyl)-2-O--d-galactopyranosyl orientin (1) and 6?-(3-hydroxy-3-methylglutaroyl)-2-O--d-galactopyranosyl vitexin (2) on the basis of various spectroscopic analysis (including different 1D and 2D NMR spectroscopies, high-resolution electrospray ionization mass spectrometry) and chemical evidences. Bioassay showed that eight flavonoids inhibited complement activation on the classic pathway in vitro, with their IC50 values ranging from 0.88 to 4.02mM, which may contribute to the applications of the herb in treatment of acute respiratory distress syndrome, etc.
• Controlled acid hydrolysis and kinetics of flavone C-glycosides from trollflowers
  作者：Mian Dou、Xi-Hui He、Yan Sun、Fang Peng、Jiang-Yun Liu、Li-Li Hao、Shi-Lin Yang

  DOI：10.1016/j.cclet.2014.11.021

  日期：2015.2

  Acid hydrolysis mechanisms of orientin-2 ''-O-galactopyranoside (OGA), orientin and other flavone C-glycosides in the trollflowers (Trollius chinensis Bunge) were studied in this report for the first time. Hydrolysis parameters including temperature, acidity, solvent and reaction time were comprehensively investigated. OGA could be hydrolyzed to orientin, followed by an isomerization to isoorientin via a reversible Wessely-Moser rearrangement reaction under stronger acidic conditions. A first-order kinetic model fitted the hydrolysis process of OGA well. Under the optimal hydrolysis conditions of 80 degrees C, 1.0 mol/L H+ and 7 h reaction time, about 77% OGA was transformed to orientin with no detectable isoorientin. These results could be helpful for better understanding of the acid hydrolysis kinetics of flavone C-glycosides, as well as the preparation of these valuable components under controlled acid hydrolysis conditions. (C) 2014 Jiang-Yun Liu. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.