cyanidin 3-O-[2-O-(β-glucopyranosyl)-6-O-(trans-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside] | 1104563-96-3

• 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: cyanidin 3-O-[2-O-(β-glucopyranosyl)-6-O-(trans-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside]
• 英文别名: 3-[[(2R,3S,4S,5R,6S)-6-[3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[3-(4-hydroxyphenyl)prop-2-enoyloxymethyl]-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-7-hydroxychromenylium-5-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3-oxopropanoic acid
• CAS: 1104563-96-3
• 化学式: C₄₅H₄₉O₂₆
• 分子量: 1005.87
• InChiKey: MOKXXHGUHGXGFE-MKSLPENWSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -2.33
• 重原子数：
  71
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  409
• 氢给体数：
  14
• 氢受体数：
  25

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  cyanidin 3-O-[2-O-(β-glucopyranosyl)-6-O-(4-O-(β-glucopyranosyl)-trans-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside] 在 盐酸 、 水 作用下， 反应 0.17h， 生成 cyanidin 3-O-[2-O-(β-glucopyranosyl)-6-O-(trans-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside] 、 cyanidin 3-sophoroside-5-glucoside 、 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.