delphinidin 3-O-glucoside-5-O-glucoside | 17670-06-3

• 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: delphinidin 3-O-glucoside-5-O-glucoside
• 英文别名: delphinidin 3,5-β-D-glucoside；delphinidin-3,5-O-bis-glucoside；delphinidin-3,5-O-diglucoside；delphinidin 3,5-diglucoside；delphinidin-3,5-O-glucoside；delphinidin-3,5-glucoside；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[7-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromenylium-5-yl]oxyoxane-3,4,5-triol
• CAS: 17670-06-3；47851-70-7
• 化学式: C₂₇H₃₁O₁₇
• 分子量: 627.533
• InChiKey: XCTGXGVGJYACEI-LCENJUANSA-O

物化性质

• 物理描述：
  Solid
• 熔点：
  202-203°C

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

安全信息

• WGK Germany：
  3
• 储存条件：
  -20°C

制备方法与用途

Delphinidin 3,5-二葡萄糖苷是一种花青素，可以从石榴（Punica granatum）中提取得到。

反应信息

• 作为产物：
  描述：

  awobanin chloride 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.75h， 生成 delphinidin 3-O-glucoside-5-O-glucoside
  参考文献：
  名称：

  Participation of p-coumaroyl glucose residue of awobanin in synthesis of the complex molecule of commelinin

  摘要：

  DOI：

  10.1016/s0031-9422(00)82218-9

文献信息

• Structure of anthocyanin from the blue petals of Phacelia campanularia and its blue flower color development
  作者：Mihoko Mori、Tadao Kondo、Kenjiro Toki、Kumi Yoshida

  DOI：10.1016/j.phytochem.2005.12.024

  日期：2006.3

  The dicaffeoyl anthocyanin, phacelianin, was isolated from blue petals of Phacelia campanularia. Its structure was determined to be 3-O-(6-O-(4'-O-(6-O-(4'-O-beta-d-glucopyranosyl-(E)-caffeoyl)-beta-d-glucopyranosyl)-(E)-caffeoyl)-beta-d-glucopyranosyl)-5-O-(6-O-malonyl-beta-d-glucopyranosyl)delphinidin. The CD of the blue petals of the phacelia showed a strong negative Cotton effect and that of the

  双咖啡酰花青素，phacelianin，是从Phacelia campanularia 的蓝色花瓣中分离出来的。其结构被确定为 3-O-(6-O-(4'-O-(6-O-(4'-O-β-d-吡喃葡萄糖基-(E)-caffeoyl)-β-d-吡喃葡萄糖基)-(E)-咖啡酰)-β-d-吡喃葡萄糖基)-5-O-(6-O-丙二酰-β-d-吡喃葡萄糖基)飞燕草素。phacelia蓝色花瓣的CD显示出强烈的负Cotton效应，有色原生质体悬浮液的CD相同，表明phacelianin的生色团可能在蓝色液泡中以逆时针堆积的方式进行分子间堆积. 在弱酸性水溶液中，phacelianin 在 CD 中显示出与花瓣相同的蓝色和负棉花效应。然而，在没有金属离子的情况下逐渐形成蓝黑色沉淀。可能需要极少量的 Al(3+) 或 Fe(3+) 来稳定蓝色溶液。Phacelianin 可能同时采取分子间和分子内堆积的形式，通
• Molecular and biochemical characterization of the UDP-glucose: Anthocyanin 5-O-glucosyltransferase from Vitis amurensis
  作者：Fei He、Wei-Kai Chen、Ke-Ji Yu、Xiang-Nan Ji、Chang-Qing Duan、Malcolm J. Reeves、Jun Wang

  DOI：10.1016/j.phytochem.2015.06.023

  日期：2015.9

  Generally, red Vitis vinifera grapes only contain monoglucosidic anthocyanins, whereas most non-vinifera red grapes of the Vitis genus have both monoglucosidic and bis-glucosidic anthocyanins, the latter of which are believed to be more hydrophilic and more stable. Although previous studies have established the biosynthetic mechanism for formation of monoglucosidic anthocyanins, less attention has been paid to that of bis-glucosidic anthocyanins. In the present research, the full-length cDNA of UDP-glucose: anthocyanin 5-0-glucosyltransferase from Vitis amurensis Rupr. cv. 'Zuoshanyi' grape (Va5GT) was cloned. After acquisition and purification of recombinant Va5GT, its enzymatic parameters were systematically analyzed in vitro. Recombinant Va5GT used malvidin-3-O-glucoside as its optimum glycosidic acceptor when UDP-glucose was used as the glycosidic donor. Va5GT-GFP was found to be located in the cytoplasm by analyzing its subcellular localization with a laser-scanning confocal fluorescence microscope, and this result was coincident with its metabolic function of modifying anthocyanins in grape cells. Furthermore, the relationship between the transcriptional expression of Va5GT and the accumulation of anthocyanidin bis-glucosides during berry development suggested that Va5GT is a key enzyme in the biosynthesis of bis-glucosidic anthocyanins in V. amurensis grape berries. (C) 2015 Elsevier Ltd. All rights reserved.
• Participation of p-coumaroyl glucose residue of awobanin in synthesis of the complex molecule of commelinin
  作者：Kŏsaku Takeda、Fumiko Narashima、Shigeru Nonaka

  DOI：10.1016/s0031-9422(00)82218-9

  日期：1980.1