矮牵牛素-3-O-葡萄糖 | 71991-88-3

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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: 矮牵牛素-3-O-葡萄糖
• 英文名称: petunidin-3-O-glucoside
• 英文别名: 3-O-β-D-glucopyranoside of petunidin；3-O-(β-D-glucopyranosyl)petunidin；petunidin 3-O-β-D-glucopyranoside；3-O-β-D-glucopyranosyl petunidin；petunidin 3-O-β-glucopyranoside；petunidin-3-O-β-glucopyranoside；Petunidin 3-glucoside；(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 71991-88-3
• 化学式: C₂₂H₂₃O₁₂
• 分子量: 479.417
• InChiKey: CCQDWIRWKWIUKK-QKYBYQKWSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  0.39
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  191
• 氢给体数：
  8
• 氢受体数：
  11

安全信息

• 储存条件：
  -20°C，密封保存，置于干燥处。

反应信息

• 作为反应物：
  描述：

  矮牵牛素-3-O-葡萄糖 在 氘代甲醇 、 氘代三氟乙酸 作用下， 生成
  参考文献：
  名称：

  花色苷和吡喃花色素的反应性。甲醇中芳香族氢-氘交换反应的研究。

  摘要：

  涉及花青素结构及其平衡形式的反应性研究将使人们更好地理解这些抗氧化剂的性质。氢-氘（H-> D）在delphinidin（1），petunidin（2），malvidin（3）的相应部位和羧基吡喃去甲酚苷（4），羧基pyranopetunidin（ 5），在室温下，在纯净CD 3OD和CF 3CO 2D酸化的CD 3OD中，对羧基吡喃酮抗生物素蛋白（6）和黄酮醇槲皮素3-O-（6-α-鼠李糖吡喃糖基-β-吡喃葡萄糖苷）（7）进行了检测。由（1）H NMR积分数据确定的H-6和H-8的H-> D交换常数为2，独立于颜料浓度（最高4 x 10（-2）M）和三氟乙酸酸浓度（0-15％，v / v）。这表明这些反应遵循一级动力学，并且出乎意料地与酸浓度无关。1-3的黄酮阳离子A环的H-6和H-8，以及在相应的半酮形式的氢中，与约100 h（1）和约50 h（2和3）的半衰期交换， 分别。吡喃花色素（4-6）没有发生类似氢的H->

  DOI：

  10.1021/jf071132f

文献信息

• Acid Mediated Hydrolysis of Blueberry Anthocyanins.
  作者：Takashi ICHIYANAGI、Kikuo OIKAWA、Chigusa TATEYAMA、Tetsuya KONISHI

  DOI：10.1248/cpb.49.114

  日期：——

  Acid mediated hydrolysis of anthocyanins was studied using capillary zone electrophoresis (CZE). A commercially available wild blueberry (Bilberry) extract was dissolved in different concentrations of TFA (0.1, 1, 3, 9%), then was subjected to thermodecomposition reaction at 95 °C. After the reaction, the samples were analyzed by CZE. The hydrolysis rate of each anthocyanin and the formation of the aglycon were determined by the change in the peak pattern of the anthocyanins in the electropherogram. Each anthocyanin peak decreased time dependently in a first order kinetic fashion. It was revealed that the hydrolysis rate of each anthocyanin was determined primarily by the type of conjugated sugar and not by the aglycon structure. The rate constant of anthocyanin hydrolysis was in the following order, arabinoside>galactoside>glucoside without regard to the aglycon structure. The kinetic behavior of this anthocyanin hydrolysis together with the CZE mobility allowed us to identify an unknown CZE peak as delphinidin 3-O-β-arabinoside. At low TFA concentration, significant decomposition of the anthocyanidin nucleus occurred, but the glycoside hydrolysis predominated at high TFA concentration. It was further revealed that the aglycon released reacted successively to form polymeric products at higher TFA conditions.

  使用毛细管区带电泳 (CZE) 研究了酸介导的花青素水解。将市售的野生蓝莓（Bilberry）提取物溶解在不同浓度的TFA（0.1、1、3、9%）中，然后在95℃下进行热分解反应。反应后，通过 CZE 分析样品。通过电泳图中花青素峰模式的变化来确定每种花青素的水解速率和苷元的形成。每个花青素峰以一级动力学方式随时间下降。结果表明，每种花青素的水解率主要由共轭糖的类型决定，而不是由苷元结构决定。花青素水解速率常数的顺序为：阿拉伯糖苷>半乳糖苷>葡萄糖苷，与苷元结构无关。这种花青素水解的动力学行为以及 CZE 迁移率使我们能够将未知的 CZE 峰识别为花翠素 3-O-β-阿拉伯糖苷。在低TFA浓度下，花青素核发生显着分解，但在高TFA浓度下糖苷水解占主导地位。进一步揭示，释放的苷元在较高的TFA条件下连续反应形成聚合产物。
• 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.
• Antioxidant and Cellular Activities of Anthocyanins and Their Corresponding Vitisins AStudies in Platelets, Monocytes, and Human Endothelial Cells
  作者：María García-Alonso、Gerald Rimbach、Julián C. Rivas-Gonzalo、Sonia de Pascual-Teresa

  DOI：10.1021/jf035360v

  日期：2004.6.1

  During red wine aging, there is a loss of anthocyanins and the formation of various other pigments, so-called vitisins A, which are formed through the chemical interaction of the original anthocyanins with pyruvic acid. The objective of this study was to investigate the antioxidant activities of the most abundant anthocyanins present in red wine (glycosides of delphinidin, petunidin, and malvidin) and their corresponding vitisins A. Anthocyanins exhibited a higher iron reducing as well as 2,2'-azinobis (3-ethyl-benzothiazoline-6-sulfonate) and peroxyl radical scavenging activity than their corresponding vitisins A. Delphinidin showed the highest antioxidant effect of the tested compounds in all of the assays used. Furthermore, we studied the effect of anthocyanins and vitisins A on platelet aggregation and monocyte and endothelial function. Anthocyanins and vitisins did not affect nitric oxide production and tumor necrosis factor-alpha (TNF-alpha) secretion in lipopolysaccharide plus interferon-gamma-activated macrophages. Furthermore, anthocyanins and vitisins did not change collagen-induced platelet aggregation in vitro. However, anthocyanins and to a lesser extent vitisins exhibited protective effects against TNF-alpha-induced monocyte chemoattractant protein production in primary human endothelial cells.
• Reactivity of Anthocyanins and Pyranoanthocyanins. Studies on Aromatic Hydrogen–Deuterium Exchange Reactions in Methanol
  作者：Monica Jordheim、Torgils Fossen、Jon Songstad、Øyvind M. Andersen

  DOI：10.1021/jf071132f

  日期：2007.10.1

  hydrogens of the hemiketal forms, exchanged with half-lives of approximately 100 h ( 1) and approximately 50 h ( 2 and 3), respectively. The pyranoanthocyanins (4-6) experienced no H --> D exchange for the analogous hydrogens, but H --> D exchange of H-beta (H-4)(t 1/2 approximately 25 h) for these compounds was observed. Only H-8 underwent significant H --> D exchange in 7. It is concluded that a stabilization

  涉及花青素结构及其平衡形式的反应性研究将使人们更好地理解这些抗氧化剂的性质。氢-氘（H-> D）在delphinidin（1），petunidin（2），malvidin（3）的相应部位和羧基吡喃去甲酚苷（4），羧基pyranopetunidin（ 5），在室温下，在纯净CD 3OD和CF 3CO 2D酸化的CD 3OD中，对羧基吡喃酮抗生物素蛋白（6）和黄酮醇槲皮素3-O-（6-α-鼠李糖吡喃糖基-β-吡喃葡萄糖苷）（7）进行了检测。由（1）H NMR积分数据确定的H-6和H-8的H-> D交换常数为2，独立于颜料浓度（最高4 x 10（-2）M）和三氟乙酸酸浓度（0-15％，v / v）。这表明这些反应遵循一级动力学，并且出乎意料地与酸浓度无关。1-3的黄酮阳离子A环的H-6和H-8，以及在相应的半酮形式的氢中，与约100 h（1）和约50 h（2和3）的半衰期交换， 分别。吡喃花色素（4-6）没有发生类似氢的H->