3-O-(6-O-(E-p-coumaryl)-2-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl)-5-O-(β-D-glucopyranosyl)cyanidin

• 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: 3-O-(6-O-(E-p-coumaryl)-2-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl)-5-O-(β-D-glucopyranosyl)cyanidin
• 英文别名: cyanidin 3-O-[2-O-(β-glucopyranosyl)-6-O-(trans-p-coumaroyl)-β-glucopyranoside]-5-(β-glucopyranoside)；[(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-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• 化学式: C₄₂H₄₇O₂₃
• 分子量: 919.821
• InChiKey: XOEXPZWQKSJHLH-GXKMNUNHSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -2.35
• 重原子数：
  65
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  366
• 氢给体数：
  14
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  3-O-(6-O-(E-p-coumaryl)-2-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl)-5-O-(β-D-glucopyranosyl)cyanidin 以 aq. phosphate buffer 为溶剂， 反应 24.0h， 生成 原儿茶酸
  参考文献：
  名称：

  在温和的中性溶液中酰化花色苷的去向

  摘要：

  在中性溶液中，被羟基肉桂酸酰化的花色苷与它们的非酰化同系物相比，通常呈现出诱人的蓝色和更高的抗色差性。但是，它们仍然容易受到氧化反应和水解反应的了解不足，而氧化反应和水解反应强烈地导致颜色损失并限制了其工业应用。在这项工作中，通过UPLC-DAD-MS（高分辨率和高分辨率）研究了分离的红甘蓝花色苷（0、1或2个酰基）在pH 7下的热降解。观察到非氧化性变化，包括脱酰基和分子内酰基转移，发现它们很大程度上取决于酰基的数量和位置以及铁离子的存在。在中度和高级热降解下，有几种氧化机理被证明可导致原儿茶酸，间苯二甲醛2-O-葡糖苷，酰基糖苷和2,4,6-三羟基苯基乙酸和3,5,7-三羟基香豆素的衍生物。根据观察到的产品分布和添加铁的影响2+离子和H 2 O 2，讨论了可能的降解机理。它们可能以从阴离子碱（中性溶液中的主要有色形式）到O 2的一或两个电子转移开始。然后产生的过氧化氢可以作为亲电子体与

  DOI：

  10.1016/j.dyepig.2020.108326
• 作为产物：
  描述：

  cyanidin 3-O-[2-O-(β-glucopyranosyl)-6-O-(trans-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside] 在 盐酸 、 水 作用下， 反应 336.0h， 以Ca. 4 mg的产率得到3-O-(6-O-(E-p-coumaryl)-2-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl)-5-O-(β-D-glucopyranosyl)cyanidin
  参考文献：
  名称：

  Tetra-acylated cyanidin 3-sophoroside-5-glucosides from the flowers of Iberis umbellata L. (Cruciferae)

  摘要：

  The structures of 11 acylated cyanidin 3-sophoroside-5-glucosides (pigments 1-11), isolated from the flowers of Iberis umbellata cultivars (Cruciferae), were elucidated by chemical and spectroscopic methods. Pigments 1-11 were acylated with malonic acid, p-coumaric acid, ferulic acid, sinapic acid and/or glucosylhydroxycinnamic acids.Pigments 1-11 were classified into four groups by the substitution patterns of the linear acylated residues at the 3-position of the cyanidin. In the first group, pigments 1-3 were determined to be cyanidin 3-O-[2-O-(2-O-(acyl)-beta-glucopyranosyl)-6-O-(trans-p-coumaroyl)-p-glucopyranoside]-5-O-[6-O-(malonyl)-beta-glucopyranoside], in which the acyl moiety varied with none for pigment 1, ferulic acid for pigment 2 and sinapic acid for pigment 3. In the second one, pigments 4-6 were cyaniclin 3-O-[2-O-(2-O-(acyl)-beta-glucopyranosyl)-6-O-(4-O-(beta-glucopyranosyl)-trans-p-coumaroyl)-p-glucopyranosidel-5-O-[6-O-(malonyl)-p-glucopyranosidel, in which the acyl moiety varied with none for pigment 4, ferulic acid for pigment 5 and sinapic acid for pigment 6. In the third one, pigments 7-9 were cyanidin 3-O-[2-O-(2-O-(acyl)-beta-glucopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-p-glucopyranosyl)-trans-p-coumaroyl)-p-glucopyranosidel-5- 0-[6-0-(j-nalonyl)-p-glucopyranosidel, in which the acyl moiety varied with none for pigment 7, ferulic acid for pigment 8, and smapic acid for pigment 9. In the last one, pigments 10 and 11 were cyanidin 3-O-[2-O-(2-O-(acyl)-beta-glucopyranosyl)-6-O-(4-O-(6-O-(4-O-(beta-glucopyranosyl)-trans-feruloyl)-beta-glucopyranosyl)-trans-p-coumaroyl)-beta-glucopyranoside]-5-O-[6-O-(malo nyl)-p-glucopyranosidel, in which acyl moieties were none for pigment 10 and ferulic acid for pigment 11.The distribution of these pigments was examined in the flowers of four cultivars oft umbellatabyHPLC analysis. Pigment 1 acylated with one molecule ofp-coumaric acid was dominantly observed in purpleviolet cultivars. On theotherhand, pignients(9 and 11)acylated with three moleCUlesot'hydroxychinamic acids were observed in lilac (purple-violet) cultivars as major anthocyanins. The bluing effect and stability on these anthocyanin colors were discussed in relation to the molecular number ofhydroxycinnamic acids in these anthocyanin molecules. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2008.04.010

文献信息

• Tetra-acylated cyanidin 3-sophoroside-5-glucosides from the flowers of Iberis umbellata L. (Cruciferae)
  作者：Norio Saito、Fumi Tatsuzawa、Eri Suenaga、Kenjiro Toki、Koichi Shinoda、Atsushi Shigihara、Toshio Honda

  DOI：10.1016/j.phytochem.2008.04.010

  日期：2008.12

  The structures of 11 acylated cyanidin 3-sophoroside-5-glucosides (pigments 1-11), isolated from the flowers of Iberis umbellata cultivars (Cruciferae), were elucidated by chemical and spectroscopic methods. Pigments 1-11 were acylated with malonic acid, p-coumaric acid, ferulic acid, sinapic acid and/or glucosylhydroxycinnamic acids.Pigments 1-11 were classified into four groups by the substitution patterns of the linear acylated residues at the 3-position of the cyanidin. In the first group, pigments 1-3 were determined to be cyanidin 3-O-[2-O-(2-O-(acyl)-beta-glucopyranosyl)-6-O-(trans-p-coumaroyl)-p-glucopyranoside]-5-O-[6-O-(malonyl)-beta-glucopyranoside], in which the acyl moiety varied with none for pigment 1, ferulic acid for pigment 2 and sinapic acid for pigment 3. In the second one, pigments 4-6 were cyaniclin 3-O-[2-O-(2-O-(acyl)-beta-glucopyranosyl)-6-O-(4-O-(beta-glucopyranosyl)-trans-p-coumaroyl)-p-glucopyranosidel-5-O-[6-O-(malonyl)-p-glucopyranosidel, in which the acyl moiety varied with none for pigment 4, ferulic acid for pigment 5 and sinapic acid for pigment 6. In the third one, pigments 7-9 were cyanidin 3-O-[2-O-(2-O-(acyl)-beta-glucopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-p-glucopyranosyl)-trans-p-coumaroyl)-p-glucopyranosidel-5- 0-[6-0-(j-nalonyl)-p-glucopyranosidel, in which the acyl moiety varied with none for pigment 7, ferulic acid for pigment 8, and smapic acid for pigment 9. In the last one, pigments 10 and 11 were cyanidin 3-O-[2-O-(2-O-(acyl)-beta-glucopyranosyl)-6-O-(4-O-(6-O-(4-O-(beta-glucopyranosyl)-trans-feruloyl)-beta-glucopyranosyl)-trans-p-coumaroyl)-beta-glucopyranoside]-5-O-[6-O-(malo nyl)-p-glucopyranosidel, in which acyl moieties were none for pigment 10 and ferulic acid for pigment 11.The distribution of these pigments was examined in the flowers of four cultivars oft umbellatabyHPLC analysis. Pigment 1 acylated with one molecule ofp-coumaric acid was dominantly observed in purpleviolet cultivars. On theotherhand, pignients(9 and 11)acylated with three moleCUlesot'hydroxychinamic acids were observed in lilac (purple-violet) cultivars as major anthocyanins. The bluing effect and stability on these anthocyanin colors were discussed in relation to the molecular number ofhydroxycinnamic acids in these anthocyanin molecules. (c) 2008 Elsevier Ltd. All rights reserved.
• The fate of acylated anthocyanins in mildly heated neutral solution
  作者：Julie-Anne Fenger、Rebecca J. Robbins、Thomas M. Collins、Olivier Dangles

  DOI：10.1016/j.dyepig.2020.108326

  日期：2020.7

  anthocyanins (0, 1 or 2 acyl groups) at pH 7 was investigated by UPLC-DAD-MS (low- and high-resolution). Non-oxidative alterations, including deacylation and intramolecular acyl transfer, were observed and found very dependent on the number and position of the acyl group(s) as well as on the presence of iron ions. At intermediate and advanced thermal degradation, several oxidative mechanisms were evidenced

  在中性溶液中，被羟基肉桂酸酰化的花色苷与它们的非酰化同系物相比，通常呈现出诱人的蓝色和更高的抗色差性。但是，它们仍然容易受到氧化反应和水解反应的了解不足，而氧化反应和水解反应强烈地导致颜色损失并限制了其工业应用。在这项工作中，通过UPLC-DAD-MS（高分辨率和高分辨率）研究了分离的红甘蓝花色苷（0、1或2个酰基）在pH 7下的热降解。观察到非氧化性变化，包括脱酰基和分子内酰基转移，发现它们很大程度上取决于酰基的数量和位置以及铁离子的存在。在中度和高级热降解下，有几种氧化机理被证明可导致原儿茶酸，间苯二甲醛2-O-葡糖苷，酰基糖苷和2,4,6-三羟基苯基乙酸和3,5,7-三羟基香豆素的衍生物。根据观察到的产品分布和添加铁的影响2+离子和H 2 O 2，讨论了可能的降解机理。它们可能以从阴离子碱（中性溶液中的主要有色形式）到O 2的一或两个电子转移开始。然后产生的过氧化氢可以作为亲电子体与