4'-O-methylcyanidin 3-O-β-D-glucopyranoside

• 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: 4'-O-methylcyanidin 3-O-β-D-glucopyranoside
• 英文别名: cyanidin-4′-O-methyl-3-glucoside；isopeonidin-3-O-β-D-glucoside；cyanidin-4'-O-methyl-3-glucoside；isopeonidin 3-O-glucoside；Isopeonidin 3-glucoside；(2S,3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₂₂H₂₃O₁₁
• 分子量: 463.418
• InChiKey: CNTWHHYMFNSRNJ-OUUKCGNVSA-O

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

• 作为产物：
  描述：

  3,4-二羟基-2'-氯苯乙酮 在 盐酸 、 三乙基硅烷 、 palladium on carbon 、 sodium hydride 、 potassium carbonate 、 sodium iodide 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 为溶剂， 反应 0.42h， 生成 4'-O-methylcyanidin 3-O-β-D-glucopyranoside
  参考文献：
  名称：

  First chemical synthesis report of an anthocyanin metabolite with in vivo occurrence: cyanidin-4′-O-methyl-3-glucoside

  摘要：

  Anthocyanins are natural polyphenolic compounds with important biological properties. In humans, these compounds are metabolized into different derivatives namely methyl, glucuronyl, and sulfate conjugates. Among these, cyanidin-4'-O-methyl-3-glucoside, already detected in vivo, seems to be an interesting metabolite to be used as standard for biological studies. The lack of suitable standards is a major drawback in biological studies. Bearing this in mind, this work describes a strategy for the chemical synthesis of cyanidin-4'-O-methyl-3-glucoside 9, which involved in the synthesis of the 'Western' and 'Eastern' molecules, namely 2,4-diacetoxy-6-hydroxybenzaldehyde 2 and 2-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3'-benzyloxy-4'-methoxyacetophenone 8, respectively. The final step consisted in the Robinson's acidic aldol condensation between 2 and 8 molecules, which after the respective deprotections yield product 9. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.100

文献信息

• Methylation of Cyanidin-3-O-Glucoside with Dimethyl Carbonate
  作者：Sarah Straßmann、Tillman Brehmer、Maike Passon、Andreas Schieber

  DOI：10.3390/molecules26051342

  日期：——

  derivatives with different degrees of methylation. Cautious identification of 4′-, 5-, and 7-OH monomethylated derivatives was also accomplished. The methylation agent used was the “green chemical” dimethyl carbonate (DMC), which is characterized by low human and ecological toxicity. The influence of the temperature, reaction time, and amount of the required diazabicyclo[5.4.0]undec-7-en (DBU) catalyst on

  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。
• 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.
• Characterization of Kinetic and Thermodynamic Parameters of Cyanidin-3-glucoside Methyl and Glucuronyl Metabolite Conjugates.
  作者：Luís Cruz、Nuno Basílio、Nuno Mateus、Fernando Pina、Victor de Freitas

  DOI：10.1021/jp511537e

  日期：2015.2.5

  The determination of rate and equilibrium constants of anthocyanin metabolites with in vivo occurrence, cyanidin-4'-O-methyl-3-glucoside (Cy4'Me3glc) and cyanidin-7-O-glucuronyl-3-glucoside (Cy7Gluc3glc), was carried out for the first time by means of direct and reverse pH jumps. The thermodynamics and kinetics of these compounds are similar to the anthocyanin monoglucosides in particular for the analogous cyanidin-3-glucoside (Cy3glc) and peonidin-3-glucoside (Peo3glc). The rate and equilibrium constants of metabolites were also compared with malvin (malvidin 3,5-diglucoside) and with a bioinspired compound 3',4'-dihydroxy-7-O-glucopyranosyloxyflavylium (DGF). In Cy4'Me3glc and Cy7Gluc3glc the rate of hydration for a fixed pH value is slower than in DGF and the dominant species at moderately acidic solutions is the hemiketal. Oppositely, in DGF trans-chalcone is the dominant species at moderately acidic solutions.