3-O-(6-O-(trans-p-coumaryl)-2-O-(2-O-(trans-sinapyl)-β-D-xylopyranosyl)-β-D-glucopyranoside)-5-O-(6-O-(malonyl)-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: 3-O-(6-O-(trans-p-coumaryl)-2-O-(2-O-(trans-sinapyl)-β-D-xylopyranosyl)-β-D-glucopyranoside)-5-O-(6-O-(malonyl)-β-D-glucopyranoside)
• 英文别名: cyanidin 3-O-[2-O-(2-O-(E-sinapoyl)-β-D-xylopyranosyl)-6-O-(E-p-coumaroyl)-β-D-glucopyranoside]-5-O-[6-O-(malonyl)-β-D-glucopyranoside]；Arabidopsis anthocyanin A9；3-[[(2R,3S,4S,5R,6S)-6-[3-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5R)-4,5-dihydroxy-3-[3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyloxy]oxan-2-yl]oxy-4,5-dihydroxy-6-[3-(4-hydroxyphenyl)prop-2-enoyloxymethyl]oxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-7-hydroxychromenylium-5-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3-oxopropanoic acid
• 化学式: C₅₅H₅₇O₂₉
• 分子量: 1182.04
• InChiKey: MAKMINQMKSULBY-GWCBQTKKSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  84
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  434
• 氢给体数：
  13
• 氢受体数：
  28

反应信息

• 作为反应物：
  描述：

  3-O-(6-O-(trans-p-coumaryl)-2-O-(2-O-(trans-sinapyl)-β-D-xylopyranosyl)-β-D-glucopyranoside)-5-O-(6-O-(malonyl)-β-D-glucopyranoside) 在 sodium hydroxide 作用下， 生成 3-O-(2-O-(β-D-xylopyranosyl)-β-D-glucopyranoside)-5-O-(β-D-glucopyranoside)
  参考文献：
  名称：

  Acylated cyanidin 3-sambubioside-5-glucosides in Matthiola incana

  摘要：

  Four acylated cyanidin 3-sambubioside-5-glucosides were isolated from purple-violet flowers of Matthiola incana and their structures were determined by chemical and spectroscopic methods. Three acylated anthocyanins were cyanidin 3-O-(6-O-acyl-2-O-(2-O-sinapyl-beta-D-xylopyranosyl)-beta-D-glucopyranosides)-5-O-(6-O-malonyl-beta-D-glucopyranosides), in which the acyl group is p-coumaryl, caffeyl or ferulyl, respectively. The remaining pigment is free from malonic acid and was identified as cyanidin 3-O-(6-O-trans-ferulyl-2-O-(2-O-trans-sinapyl-beta-D-xylopyranosyl)-beta-D-glucopyranoside)-5-O-(beta-D-glucopyranoside). Analysis of the anthocyanin constituents in 16 purple-violet cultivars revealed that they contained the above triacylated anthocyanins in variable amounts as main pigments. An aromatic pair of pigments containing sinapic and ferulic acids are considered to produce an important intramolecular effect, making bluish colours in these flowers.

  DOI：

  10.1016/0031-9422(94)00659-h

文献信息

• Acylated cyanidin 3-sambubioside-5-glucosides in Matthiola incana
  作者：Norio Saito、Fumi Tatsuzawa、Akiko Nishiyama、Masato Yokoi、Atsushi Shigihara、Toshio Honda

  DOI：10.1016/0031-9422(94)00659-h

  日期：1995.3

  Four acylated cyanidin 3-sambubioside-5-glucosides were isolated from purple-violet flowers of Matthiola incana and their structures were determined by chemical and spectroscopic methods. Three acylated anthocyanins were cyanidin 3-O-(6-O-acyl-2-O-(2-O-sinapyl-beta-D-xylopyranosyl)-beta-D-glucopyranosides)-5-O-(6-O-malonyl-beta-D-glucopyranosides), in which the acyl group is p-coumaryl, caffeyl or ferulyl, respectively. The remaining pigment is free from malonic acid and was identified as cyanidin 3-O-(6-O-trans-ferulyl-2-O-(2-O-trans-sinapyl-beta-D-xylopyranosyl)-beta-D-glucopyranoside)-5-O-(beta-D-glucopyranoside). Analysis of the anthocyanin constituents in 16 purple-violet cultivars revealed that they contained the above triacylated anthocyanins in variable amounts as main pigments. An aromatic pair of pigments containing sinapic and ferulic acids are considered to produce an important intramolecular effect, making bluish colours in these flowers.