3-[[6-O-(6-脱氧-alpha-L-甘露糖基)-beta-D-吡喃葡萄糖基]氧基]-2-(3,4-二羟基苯基)-5-(beta-D-吡喃葡萄糖基氧基)-7-羟基-1-苯并吡喃鎓 | 135558-26-8

• 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: 3-[[6-O-(6-脱氧-alpha-L-甘露糖基)-beta-D-吡喃葡萄糖基]氧基]-2-(3,4-二羟基苯基)-5-(beta-D-吡喃葡萄糖基氧基)-7-羟基-1-苯并吡喃鎓
• 英文名称: cyanidin-3-O-rutinoside-5-O-glucoside
• 英文别名: Cyanidin 3-O-rutinoside 5-O-beta-D-glucoside；(2R,3R,4R,5R,6S)-2-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol
• CAS: 135558-26-8
• 化学式: C₃₃H₄₁O₂₀
• 分子量: 757.677
• InChiKey: DFJZNAHUOVEDQB-HWKLKBEVSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -3.29
• 重原子数：
  53
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  319
• 氢给体数：
  13
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 矢车菊素-3-芸香糖苷 在 anthocyanin 5-O-glucosyltransferase from Vitis amurensis Rupr. cv. ‘Zuoshanyi’ grape 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.33h， 生成 3-[[6-O-(6-脱氧-alpha-L-甘露糖基)-beta-D-吡喃葡萄糖基]氧基]-2-(3,4-二羟基苯基)-5-(beta-D-吡喃葡萄糖基氧基)-7-羟基-1-苯并吡喃鎓
  参考文献：
  名称：

  Molecular and biochemical characterization of the UDP-glucose: Anthocyanin 5-O-glucosyltransferase from Vitis amurensis

  摘要：

  Generally, red Vitis vinifera grapes only contain monoglucosidic anthocyanins, whereas most non-vinifera red grapes of the Vitis genus have both monoglucosidic and bis-glucosidic anthocyanins, the latter of which are believed to be more hydrophilic and more stable. Although previous studies have established the biosynthetic mechanism for formation of monoglucosidic anthocyanins, less attention has been paid to that of bis-glucosidic anthocyanins. In the present research, the full-length cDNA of UDP-glucose: anthocyanin 5-0-glucosyltransferase from Vitis amurensis Rupr. cv. 'Zuoshanyi' grape (Va5GT) was cloned. After acquisition and purification of recombinant Va5GT, its enzymatic parameters were systematically analyzed in vitro. Recombinant Va5GT used malvidin-3-O-glucoside as its optimum glycosidic acceptor when UDP-glucose was used as the glycosidic donor. Va5GT-GFP was found to be located in the cytoplasm by analyzing its subcellular localization with a laser-scanning confocal fluorescence microscope, and this result was coincident with its metabolic function of modifying anthocyanins in grape cells. Furthermore, the relationship between the transcriptional expression of Va5GT and the accumulation of anthocyanidin bis-glucosides during berry development suggested that Va5GT is a key enzyme in the biosynthesis of bis-glucosidic anthocyanins in V. amurensis grape berries. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2015.06.023

文献信息

• Molecular and biochemical characterization of the UDP-glucose: Anthocyanin 5-O-glucosyltransferase from Vitis amurensis
  作者：Fei He、Wei-Kai Chen、Ke-Ji Yu、Xiang-Nan Ji、Chang-Qing Duan、Malcolm J. Reeves、Jun Wang

  DOI：10.1016/j.phytochem.2015.06.023

  日期：2015.9

  Generally, red Vitis vinifera grapes only contain monoglucosidic anthocyanins, whereas most non-vinifera red grapes of the Vitis genus have both monoglucosidic and bis-glucosidic anthocyanins, the latter of which are believed to be more hydrophilic and more stable. Although previous studies have established the biosynthetic mechanism for formation of monoglucosidic anthocyanins, less attention has been paid to that of bis-glucosidic anthocyanins. In the present research, the full-length cDNA of UDP-glucose: anthocyanin 5-0-glucosyltransferase from Vitis amurensis Rupr. cv. 'Zuoshanyi' grape (Va5GT) was cloned. After acquisition and purification of recombinant Va5GT, its enzymatic parameters were systematically analyzed in vitro. Recombinant Va5GT used malvidin-3-O-glucoside as its optimum glycosidic acceptor when UDP-glucose was used as the glycosidic donor. Va5GT-GFP was found to be located in the cytoplasm by analyzing its subcellular localization with a laser-scanning confocal fluorescence microscope, and this result was coincident with its metabolic function of modifying anthocyanins in grape cells. Furthermore, the relationship between the transcriptional expression of Va5GT and the accumulation of anthocyanidin bis-glucosides during berry development suggested that Va5GT is a key enzyme in the biosynthesis of bis-glucosidic anthocyanins in V. amurensis grape berries. (C) 2015 Elsevier Ltd. All rights reserved.