cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-3-O-(β-glucopyranosyl)-β-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-β-glucopyranosyl)-trans-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-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: cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-3-O-(β-glucopyranosyl)-β-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-β-glucopyranosyl)-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-3-[(2S,3R,4S,5R)-5-hydroxy-3-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxy]-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-[[(E)-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxymethyl]oxan-2-yl]oxyphenyl]prop-2-enoyl]oxymethyl]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: C₇₆H₈₃O₄₁
• 分子量: 1652.47
• InChiKey: BGFLKNQEJZCJSX-HORUMCLFSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -2.43
• 重原子数：
  117
• 可旋转键数：
  33
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  618
• 氢给体数：
  19
• 氢受体数：
  40

反应信息

• 作为反应物：
  描述：

  cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-3-O-(β-glucopyranosyl)-β-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-β-glucopyranosyl)-trans-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside] 在 水 、 sodium hydroxide 作用下， 生成 阿魏酸 、 丙二酸 、 cyanidin3-(3^X-glucosylsambubioside)-5-glucoside 、 1-O-p-hydroxycinnamoyl-β-D-glucopyranose
  参考文献：
  名称：

  Acylated cyanidin glycosides from the pale-violet flowers of Ionopsidium acaule (Desf.) Rchb. (Brassicaceae)

  摘要：

  Three new acylated cyanidin 3-sambubioside-5-glucosides (1-3) and one new acylated cyanidin 3-(3(X)-glucosylsambubioside)-5-glucoside (4) were isolated from the pale-violet flowers of Ionopsidium acaule (Desf.) Rch beta, together with one known anthocyanin. These new pigments were determined by chemical and spectroscopic methods to be cyanidin 3-O-[2-O-(beta-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-beta- glucopyranosyl)-trans-p-coumaroyl)-b-glucopyranoside]-5-O-[6-O-(malonyl)-b-glucopyranoside] (1), cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-beta-xylopyranosyl)-6-O-(4-O-(beta-glucopyranosyl)-trans-pcoumaroyl)-beta-glucopyranoside]-5-O-[6-O-(malonyl)-b-glucopyranoside] (2), cyanidin 3-O-[2-O-(2-O( trans-feruloyl)-beta-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-beta-glucopyranosyl)-trans-p-coumaroyl)- b-glucopyranoside]-5-O-[6-O-(malonyl)-beta-glucopyranoside] (3) and cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-3-O-(beta-glucopyranosyl)-beta-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-b-glucopyranosyl)- trans-p-coumaroyl)-beta-glucopyranoside]-5-O-[6-O-(malonyl)-beta-glucopyranoside] (4). These polyacylated cyanidin glycosides are responsible for the pale-violet flower color of I. acaule, and the contribution of the number of hydroxycinnamic acid residues to the bluing effect was discussed. (C) 2013 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.phytol.2013.10.004

文献信息

• Acylated cyanidin glycosides from the pale-violet flowers of Ionopsidium acaule (Desf.) Rchb. (Brassicaceae)
  作者：Fumi Tatsuzawa、Narumi Takahashi、Kazuhisa Kato、Koichi Shinoda、Norio Saito、Toshio Honda

  DOI：10.1016/j.phytol.2013.10.004

  日期：2014.2

  Three new acylated cyanidin 3-sambubioside-5-glucosides (1-3) and one new acylated cyanidin 3-(3(X)-glucosylsambubioside)-5-glucoside (4) were isolated from the pale-violet flowers of Ionopsidium acaule (Desf.) Rch beta, together with one known anthocyanin. These new pigments were determined by chemical and spectroscopic methods to be cyanidin 3-O-[2-O-(beta-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-beta- glucopyranosyl)-trans-p-coumaroyl)-b-glucopyranoside]-5-O-[6-O-(malonyl)-b-glucopyranoside] (1), cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-beta-xylopyranosyl)-6-O-(4-O-(beta-glucopyranosyl)-trans-pcoumaroyl)-beta-glucopyranoside]-5-O-[6-O-(malonyl)-b-glucopyranoside] (2), cyanidin 3-O-[2-O-(2-O( trans-feruloyl)-beta-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-beta-glucopyranosyl)-trans-p-coumaroyl)- b-glucopyranoside]-5-O-[6-O-(malonyl)-beta-glucopyranoside] (3) and cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-3-O-(beta-glucopyranosyl)-beta-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-b-glucopyranosyl)- trans-p-coumaroyl)-beta-glucopyranoside]-5-O-[6-O-(malonyl)-beta-glucopyranoside] (4). These polyacylated cyanidin glycosides are responsible for the pale-violet flower color of I. acaule, and the contribution of the number of hydroxycinnamic acid residues to the bluing effect was discussed. (C) 2013 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.