cyanidin 3-O-[6-O-(2-O-(trans-caffeoyl)-α-arabinofuranosyl)-β-glucopyranoside]-7,3'-O-di[6-O-(trans-caffeoyl)-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-[6-O-(2-O-(trans-caffeoyl)-α-arabinofuranosyl)-β-glucopyranoside]-7,3'-O-di[6-O-(trans-caffeoyl)-β-glucopyranoside]
• 英文别名: monodecaffeoylzebrinin；[(2R,3S,4S,5R,6S)-6-[3-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-2-[3-[(2S,3R,4S,5S,6R)-6-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-4-hydroxyphenyl]-5-hydroxychromenylium-7-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 化学式: C₆₅H₆₇O₃₄
• 分子量: 1392.23
• InChiKey: NQLPROKRJQDBGY-BZYNXHDWSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -1.18
• 重原子数：
  99.0
• 可旋转键数：
  22.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  548.41
• 氢给体数：
  19.0
• 氢受体数：
  33.0

反应信息

• 作为反应物：
  描述：

  cyanidin 3-O-[6-O-(2-O-(trans-caffeoyl)-α-arabinofuranosyl)-β-glucopyranoside]-7,3'-O-di[6-O-(trans-caffeoyl)-β-glucopyranoside] 生成 花色素 、 L-阿拉伯糖 、 葡萄糖 、 TRANS-咖啡酸
  参考文献：
  名称：

  Triacylated Anthocyanidin 3-Arabinosylglucoside-7,3’-diglucosides Isolated from the Bluish Flowers of Tradescantia virginiana Cultivars and Their Distribution in the Tradescantieae

  摘要：

  Two triacylated anthocyanidin 3-arabinosylglucoside-7,3'-diglucosides were isolated from the purple-violet violet-blue flowers of Tradescantia virginiana cultivars. The structures were determined to be 3-O-[6-O-(2-O-(trans-caffeoyl)-alpha-arabinofuranosyl)-beta-glucopyranoside]-7,3'-O- di-[6-O-(trans-caffeoyl)-(beta-glucopyranoside]s of delphinidin and cyanidin. The former is a new anthocyanin in plants, whereas the latter, a rare anthocyanin has been recognized to be present in Zebrina pendula. Both anthocyanins exhibited typical three lambda max in the visible region at 537, 574 and 620 nm for the delphinidin glycoside and at 510, 545 and 580 nm for the cyanidin glycoside in a 5.6 pH solution. These spectroscopic characteristics might be responsible for forming the intramolecular co-pigmentation between anthocyanidin and caffeic acid residues in these pigments. By HPLC analysis of nine species of the tribe Tradescantieae it was revealed that polyacylated anthocyanidin 3-arabinosylglucoside-7,3'-diglucosides were commonly found in all these plants as their major anthocyanins.

  DOI：

  10.3987/com-10-12012

文献信息

• Triacylated Anthocyanidin 3-Arabinosylglucoside-7,3’-diglucosides Isolated from the Bluish Flowers of Tradescantia virginiana Cultivars and Their Distribution in the Tradescantieae
  作者：Fumi Tatsuzawa、Norio Saito、Kazushi Maeyama、Masato Yokoi、Atsushi Shigihara、Toshio Honda

  DOI：10.3987/com-10-12012

  日期：——

  Two triacylated anthocyanidin 3-arabinosylglucoside-7,3'-diglucosides were isolated from the purple-violet violet-blue flowers of Tradescantia virginiana cultivars. The structures were determined to be 3-O-[6-O-(2-O-(trans-caffeoyl)-alpha-arabinofuranosyl)-beta-glucopyranoside]-7,3'-O- di-[6-O-(trans-caffeoyl)-(beta-glucopyranoside]s of delphinidin and cyanidin. The former is a new anthocyanin in plants, whereas the latter, a rare anthocyanin has been recognized to be present in Zebrina pendula. Both anthocyanins exhibited typical three lambda max in the visible region at 537, 574 and 620 nm for the delphinidin glycoside and at 510, 545 and 580 nm for the cyanidin glycoside in a 5.6 pH solution. These spectroscopic characteristics might be responsible for forming the intramolecular co-pigmentation between anthocyanidin and caffeic acid residues in these pigments. By HPLC analysis of nine species of the tribe Tradescantieae it was revealed that polyacylated anthocyanidin 3-arabinosylglucoside-7,3'-diglucosides were commonly found in all these plants as their major anthocyanins.