delphinidin 3-O-β-D-glucopyranoside-7-O-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: delphinidin 3-O-β-D-glucopyranoside-7-O-β-D-glucopyranoside
• 英文别名: delphinidin-3,7-β-O-diglucoside；Delphinidin 3,7-di-O-beta-D-glucoside；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[5-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromenylium-7-yl]oxyoxane-3,4,5-triol
• 化学式: C₂₇H₃₁O₁₇
• 分子量: 627.533
• InChiKey: JVROXMCODLRLLV-LCENJUANSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -2.44
• 重原子数：
  44
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  281
• 氢给体数：
  12
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  (6''-O-(delphinidin 3-O-(6''-O-p-coumaroyl-glucoside) 7-O-glucosyl)) (6''''-O-(kaempferol 3-O-glucoside, 7-O-xyloside, 4'-O-glucosyl))succinate 在 sodium hydroxide 作用下， 反应 1.0h， 生成 4-香豆酸 、 delphinidin 3-O-β-D-glucopyranoside-7-O-β-D-glucopyranoside 、 kaempferol 3,4'-di-O-glucoside-7-O-xyloside
  参考文献：
  名称：

  Covalently linked anthocyanin–flavonol pigments from blue Agapanthus flowers

  摘要：

  The structures of the two major anthucyanins in blue Agapanthus flowers have been determined to be a p-coumaroylated delphinidin diglycoside attached to a flavonol triglycoside via a succinic acid diester link. The structure has been determined unambiguously through degradation studies, glycosidic analysis and NMR experiments. These compounds represent unique examples of anthocyanin pigments where both types of co-pigment, an aromatic acyl group and a flavonoid co-pigment, are attached covalently to the anthocyanin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00572-5

文献信息

• 7-Polyacylated delphinidin 3,7-diglucosides from the blue flowers of Leschenaultia cv. Violet Lena
  作者：Norio Saito、Fumi Tatsuzawa、Yoshikazu Yazaki、Atsushi Shigihara、Toshio Honda

  DOI：10.1016/j.phytochem.2006.11.012

  日期：2007.3

  The triacyl anthocyanins, Leschenaultia blue anthocyanins 1 and 2 (LBAs 1 and 2) were isolated from the blue flowers of Leschenaultia R. Br. cv. Violet Lena (Goodeniaceae), in which LBA 1 was present as a dominant pigment. The structure of LBA I was elucidated to be delphinidin 3-O-[6-O-(malonyl)-beta-D-glucopyranoside]-7-O-[beta-D-(4-O-(beta-O-(4-O-(P-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glueopyranosyl)-trans-caffeoyl)-beta-D-glucopyranoside] by application of chemical and spectroscopic methods. Since LAB 2 was isolated in small amount, its structure was tentatively assigned as either delphinidin 3-(malonylglucoside)-7-[(glucosyl-p-coumaroyl)-(glucosylcaffeoyl)glucoside] or delphinidin 3-(malonyl-gluco side)-7-[(glucosyl-caffeoyl)(glucosyl-p-coumaroyl)-glucoside]. This is the first report of the occurrence of 7-polyacylated anthocyanins in the family of Goodeniaceae, although others have been found in the families of the Ranunculaceac, Campanulaceae, and Compositae. Moreover, delphinidin 3-glycoside-7-di-(glucosylcaffeoyl)-glucoside has been reported only in the flowers of Platycodon grandflorum (Campanulaceae). From a chemotaxonomical viewpoint, the Goodeniaceae may be closely related to the Campanulaceae. (c) 2006 Elsevier Ltd. All rights reserved.