2-(3,4-二羟基苯基)-3-(alpha-D-吡喃半乳糖基氧基)-5,7-二羟基-4H-1-苯并吡喃-4-酮 | 65549-68-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 2-(3,4-二羟基苯基)-3-(alpha-D-吡喃半乳糖基氧基)-5,7-二羟基-4H-1-苯并吡喃-4-酮
• 英文名称: quercetin-3-O-galactoside
• 英文别名: 3-quercetin-galactoside；hyperoside；hyperin；4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(alpha-D-galactopyranosyloxy)-5,7-dihydroxy-；2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS: 65549-68-0
• 化学式: C₂₁H₂₀O₁₂
• 分子量: 464.383
• InChiKey: OVSQVDMCBVZWGM-PRPRGGMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  207
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  尿苷 5’-二二氧磷基半乳糖二钠盐 、 槲皮素 在 recombinant poplar flavonoid galactosyltransferase PtUGT₇₈L₁ 作用下， 以 aq. buffer 为溶剂， 反应 0.5h， 生成 2-(3,4-二羟基苯基)-3-(alpha-D-吡喃半乳糖基氧基)-5,7-二羟基-4H-1-苯并吡喃-4-酮
  参考文献：
  名称：

  Molecular cloning and biochemical characterization of two UDP-glycosyltransferases from poplar

  摘要：

  Two pathogen-induced uridine diphosphate glycosyltransferases (UGTs) identified previously via co-expression with induced proanthocyanidin (PA) synthesis in poplar were cloned and characterized. Phylogenetic analysis grouped both genes with other known flavonoid UGTs that act on flavonols and anthocyanins. Recombinant enzymes were produced in order to test if they could glycoslate flavonoids. PtUGT78L1 accepted the flavonols quercetin and kaempferol as well as cyanidin, and used UDP-galactose as a sugar donor. PtUGT78M1 did not accept any of the flavonoids tested as a substrate, but did transfer glucose from UDP-glucose to the universal substrate 2,4,6-trichlorophenol. However, neither enzyme acted on the flavan-3-ols catechin or epicatechin, intermediates in the PA biosynthetic pathway. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2012.12.012

文献信息

• Molecular cloning and biochemical characterization of two UDP-glycosyltransferases from poplar
  作者：Vasko Veljanovski、C. Peter Constabel

  DOI：10.1016/j.phytochem.2012.12.012

  日期：2013.7

  Two pathogen-induced uridine diphosphate glycosyltransferases (UGTs) identified previously via co-expression with induced proanthocyanidin (PA) synthesis in poplar were cloned and characterized. Phylogenetic analysis grouped both genes with other known flavonoid UGTs that act on flavonols and anthocyanins. Recombinant enzymes were produced in order to test if they could glycoslate flavonoids. PtUGT78L1 accepted the flavonols quercetin and kaempferol as well as cyanidin, and used UDP-galactose as a sugar donor. PtUGT78M1 did not accept any of the flavonoids tested as a substrate, but did transfer glucose from UDP-glucose to the universal substrate 2,4,6-trichlorophenol. However, neither enzyme acted on the flavan-3-ols catechin or epicatechin, intermediates in the PA biosynthetic pathway. (C) 2013 Elsevier Ltd. All rights reserved.