3,7-bisbenzyloxy-2-(3-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-4-benzyloxyphenyl)-5-hydroxyl-4H-chromen-4-one | 357194-12-8

• 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: 3,7-bisbenzyloxy-2-(3-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-4-benzyloxyphenyl)-5-hydroxyl-4H-chromen-4-one
• 英文别名: 3,4',7-tri-O-benzylquercetin-3'-O-tetra-O-acetyl-β-D-glucopyranoside；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[5-[5-hydroxy-4-oxo-3,7-bis(phenylmethoxy)chromen-2-yl]-2-phenylmethoxyphenoxy]oxan-2-yl]methyl acetate
• CAS: 357194-12-8
• 化学式: C₅₀H₄₆O₁₆
• 分子量: 902.906
• InChiKey: LUSILKVRHHQQNY-DQTUZKKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  66
• 可旋转键数：
  21
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  198
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  3,7-bisbenzyloxy-2-(3-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-4-benzyloxyphenyl)-5-hydroxyl-4H-chromen-4-one 在 sodium methylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 2-(3-β-D-glucopyranosyloxy-4-benzyloxyphenyl)-3,5,7-tribenzyloxy-4H-chromen-4-one
  参考文献：
  名称：

  Regiospecific synthesis of quercetin O-β-d-glucosylated and O-β-d-glucuronidated isomers

  摘要：

  Quercetin, the polyphenolic compound, which has the highest daily intake, is well known for its protective effects against aging diseases and has received a lot of attention for this reason. Both quercetin 3-O-beta-D-glucuronide and quercetin 3'-O-beta-D-glucuronide are human metabolites, which, together with their regioisomers, are required for biological as well as physical chemistry studies. We present here a novel synthetic route based on the sequential and selective protections of the hydroxyl functions of quercetin allowing selective glycosylation, followed by TEMPO-mediated oxidation to the glucuronide. This methodology enabled us to synthesize the five O-beta-D-glucosides and four O-beta-D-glucuronides of quercetin, including the major human metabolite, quercetin 3-O-beta-D-glucuronide. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.03.110
• 作为产物：
  描述：

  溴甲苯 在 三(3,6-二氧杂庚基)胺 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 3,7-bisbenzyloxy-2-(3-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-4-benzyloxyphenyl)-5-hydroxyl-4H-chromen-4-one
  参考文献：
  名称：

  Regiospecific synthesis of quercetin O-β-d-glucosylated and O-β-d-glucuronidated isomers

  摘要：

  Quercetin, the polyphenolic compound, which has the highest daily intake, is well known for its protective effects against aging diseases and has received a lot of attention for this reason. Both quercetin 3-O-beta-D-glucuronide and quercetin 3'-O-beta-D-glucuronide are human metabolites, which, together with their regioisomers, are required for biological as well as physical chemistry studies. We present here a novel synthetic route based on the sequential and selective protections of the hydroxyl functions of quercetin allowing selective glycosylation, followed by TEMPO-mediated oxidation to the glucuronide. This methodology enabled us to synthesize the five O-beta-D-glucosides and four O-beta-D-glucuronides of quercetin, including the major human metabolite, quercetin 3-O-beta-D-glucuronide. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.03.110

文献信息

• Who Is the King? The<i>α</i>-Hydroxy-<i>β</i>-oxo-<i>α</i>,<i>β</i>-enone Moiety or the Catechol B Ring: Relationship between the Structure of Quercetin Derivatives and Their Pro-Oxidative Abilities
  作者：Pei-Yan Liu、Kun Li、Ji Zhang、Da-Wei Zhang、Hong-Hui Lin、Xiao-Qi Yu

  DOI：10.1002/cbdv.200900032

  日期：2010.1

  Quercetin and other flavonoids have been reported to exhibit both antioxidant and pro-oxidant properties. Most studies about the pro-oxidative ability were conducted in the presence of metal ions, and the essential functional moiety of quercetin responsible for the pro-oxidative effect is still unclear. In this study, we evaluated the pro-oxidative abilities in the absence of metal ions of two quercetin

  据报道，槲皮素和其他类黄酮具有抗氧化剂和促氧化剂特性。关于促氧化能力的大多数研究是在金属离子的存在下进行的，而负责促氧化作用的槲皮素的基本功能部分仍不清楚。在这项研究中，我们评估了两种槲皮素衍生物，即槲皮素3'-O-β-D-葡萄糖苷（1）和槲皮素-3-O-β-D-的金属离子不存在时的促氧化能力葡萄糖苷（2），通过评估DNA裂解和HO（*）自由基的产生。通过荧光和粘度滴定法研究了这些化合物与DNA之间的结合方式。结果表明：1可以有效诱导质粒DNA的氧化损伤，而2则显示较差的活性。1和2均通过凹槽结合与DNA结合。