peonidin 3-O-glucoside | 68795-37-9

• 物质功能分类: 生物化工 - 核苷类药物
• 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: peonidin 3-O-glucoside
• 英文别名: 3'-O-methylcyanidin 3-O-β-D-glucopyranoside；3-O-β-D-glucopyranoside of peonidin；3-O-(β-D-glucopyranosyl)peonidin；peonidin 3-O-β-D-glucopyranoside；3-O-β-D-glucopyranosyl peonidin；peonidin 3-O-β-glucopyranoside；Peonidin-3-glucoside；(2S,3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 68795-37-9
• 化学式: C₂₂H₂₃O₁₁
• 分子量: 463.418
• InChiKey: ZZWPMFROUHHAKY-OUUKCGNVSA-O

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  0.69
• 重原子数：
  33
• 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：
  170
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 peonidin 3-O-glucoside 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 peonidin 3,5-di(β-D-glucoside) cation
  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
• 作为产物：
  描述：

  cyanidin-3-glucoside 、 碳酸二甲酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 1.5h， 生成 peonidin 3-O-glucoside
  参考文献：
  名称：

  氰基-3-O-葡糖苷与碳酸二甲酯的甲基化

  摘要：

  这项研究中提出的方法是甲基化花色苷半合成的第一个方法。有可能获得花青素3- O-具有不同甲基化程度的葡糖苷衍生物。还完成了4'-，5-和7-OH单甲基化衍生物的谨慎鉴定。所使用的甲基化剂是“绿色化学”碳酸二甲酯（DMC），其特征是对人类和生态毒性低。研究了温度，反应时间和所需的二氮杂双环[5.4.0] undec-7-en（DBU）催化剂对产物形成的影响。与使用DMC和DBU进行甲基化类黄酮的常规合成方法相比，本研究中确定的条件导致反应时间减少，并且重要的副反应，即所谓的羧甲基化，通过使用更高量的催化剂而得以最小化。

  DOI：

  10.3390/molecules26051342

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。
• Preparation and Antioxidant Activity of Ethyl-Linked Anthocyanin-Flavanol Pigments from Model Wine Solutions
  作者：Lingxi Li、Minna Zhang、Shuting Zhang、Yan Cui、Baoshan Sun

  DOI：10.3390/molecules23051066

  日期：——

  preparative scale by high-speed counter-current chromatography. The condensation reaction between each of the isolated anthocyanins and (–)-epicatechin, mediated by acetaldehyde, was conducted in model wine solutions to obtain ethyl-linked anthocyanin-flavanol pigments. The effects of pH, molar ratio, and temperature on the reaction rate were investigated, and the reaction conditions of pH 1.7, molar ratio

  花青素-黄烷醇色素是在红酒发酵和储存过程中通过花青素和黄烷醇（单体、低聚物和聚合物）之间的缩合反应形成的，是陈酿红酒中多酚的主要组别之一。然而，缺乏对其生物活性的了解。这可能是由于这些分子的结构多样性和复杂性，使得单个化合物的大规模分离和分离变得非常困难，从而限制了他们的进一步研究。在本研究中，花青素（即，malvidin-3-glucoside、cyanidin-3-glucoside 和 peonidin-3-glucoside）和 (-)-epicatechin 首先通过高速逆流色谱法以制备规模分离。每个分离的花青素和 (-)-表儿茶素之间的缩合反应，由乙醛介导，在模型葡萄酒溶液中进行，以获得乙基连接的花青素 - 黄烷醇颜料。考察了pH、摩尔比、温度对反应速率的影响，反应条件为pH 1.7，摩尔比1:6:10（花青素/(-)-表儿茶素/乙醛），反应温度35° C 被确定为将花青素转化
• Enzymatic Hemisynthesis of Metabolites and Conjugates of Anthocyanins
  作者：Iva Fernandes、Joana Azevedo、Ana Faria、Conceição Calhau、Victor de Freitas、Nuno Mateus

  DOI：10.1021/jf802844p

  日期：2009.1.28

  This work aims to study the phase II metabolization of anthocyanins that is likely to occur in vivo. Anthocyanins (delphinidin, cyanidin, and malvidin-3-glucosides) were incubated with phase II enzymes in the presence of activated cofactors in order to obtain glutathionyl conjugates, methylated and glucuronydated compounds. Overall, the three anthocyanins tested were metabolized in vitro. Two compounds were detected by HPLC after incubation of human liver cytosolic fraction with cyanidin-3-glucoside and one compound with delphinidin-3-glucoside. These compounds were identified as monomethylated products. LC-MS analysis yielded mass data that fit with the anthocyanin structures bearing an additional methyl group in ring B. Several compounds were detected by HPLC after incubation of human liver microsomes with malvidin, cyanidin, and delphinidin-3-glucosides. These compounds were identified as monoglucuron ides products after HPLC analysis. Conjugation with glutathione also occurred as proved by the mass data obtained. However, in this case, two anthocyanin equilibrium forms (flavylium and chalcone or water adducts) conjugated with glutathione were detected. Overall, the data of the present work shows the feasibility of the in vitro enzymatic hemisynthesis of metabolites and glutathione conjugates of anthocyanins. This first experimental approach may further allow the achievement of new purified forms of anthocyanins, some of which do not occur in nature, and also the determination of whether these compounds are the bioactive forms responsible for some of the biological activities reported for anthocyanins.