4'-O-Methyldelphinidin 3-O-beta-D-glucoside | 721443-68-1

• 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-Methyldelphinidin 3-O-beta-D-glucoside
• 英文别名: (2S,3R,4S,5S,6R)-2-[2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 721443-68-1
• 化学式: C₂₂H₂₃O₁₂
• 分子量: 479.417
• InChiKey: JMQNGULBWFJHCJ-NFSXTHTRSA-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

反应信息

• 作为产物：
  描述：

  飞燕草素葡萄糖苷 、 S-腺苷基-L-蛋氨碘盐 在 rat liver cytosol protein fraction 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 生成 4'-O-Methyldelphinidin 3-O-beta-D-glucoside
  参考文献：
  名称：

  Enzymatic Hemisynthesis of Metabolites and Conjugates of Anthocyanins

  摘要：

  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.

  DOI：

  10.1021/jf802844p

文献信息

• 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.