cyanidin 3-O-[2-O-(β-D-glycopyranosyl)-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: cyanidin 3-O-[2-O-(β-D-glycopyranosyl)-β-D-glucopyranoside]
• 英文别名: cyanidin-3-O-[2-O-(β-D-glycopyranosyl)-β-D-glucopyranoside]；cyanidin 3-O-(2-O-β-D-glucopyranosyl)-β-D-glucopyranoside；cyanidin-3-O-(2''-O-glucosyl)glucoside；cyanidin-3-[2-(glucosyl)glucoside]；cyanidin 3-O-sophoroside；cyanidin-3-O-sophoroside；(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₂₇H₃₁O₁₆
• 分子量: 611.534
• InChiKey: SXYMMDGPXYVCER-WGNLCONDSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -1.79
• 重原子数：
  43
• 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：
  260
• 氢给体数：
  11
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  cyanidin 3-O-[2-O-(β-D-glycopyranosyl)-β-D-glucopyranoside] 、 丙酮酸 以 水 为溶剂， 生成
  参考文献：
  名称：

  花青素糖基化方式对羧基吡喃花青素形成的影响

  摘要：

  花青素可与具有可烯丙基的化合物缩合形成吡喃花青素。这些颜料较不容易降解和变色，这与花色苷常见的亲核加成有关。这项研究旨在评估花色苷的糖基化方式对羧基吡喃花青素形成的影响。通过半制备HPLC分离了九种花色素衍生物。添加丙酮酸以诱导吡喃花青素形成。在25°C下储存31天期间，监测溶液的组成（HPLC-MS / MS），光谱（吸光度380-700 nm）和颜色（CIEL * c * h *）。带有1→6个二糖的氰基-3-糖苷产生最高的吡喃花色素苷产率（〜31％），其次是氰基-3-单糖苷（〜20％）；1→2二糖产生的吡喃花青素比例最低（5-7％）。Cyanidin-3-arabinoside转化为吡喃花色素，但在这些条件下迅速降解（3％产率）。由氰胺丁-3-槐糖苷-5-葡糖苷未形成吡喃花色素苷。糖基键比单独取代的大小更关键，而Cyanidin-3-（葡萄糖基）-（1→6）-（木糖基-（1→2）-半

  DOI：

  10.1016/j.foodchem.2018.03.117
• 作为产物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 cyanidin-3-glucoside 在 Veronica persica UDP-dependent glycosyl transferase 94F₁ 作用下， 以 potassium phosphate buffer 为溶剂， 生成 cyanidin 3-O-[2-O-(β-D-glycopyranosyl)-β-D-glucopyranoside]
  参考文献：
  名称：

  Co-pigmentation and flavonoid glycosyltransferases in blue Veronica persica flowers

  摘要：

  Glycosylation is one of the key modification steps for plants to produce a broad spectrum of flavonoids with various structures and colors. A survey of flavonoids in the blue flowers of Veronica persica Poiret (Lamiales, Scrophulariaceae), which is native of Eurasia and now widespread worldwide, led to the identification of highly glycosylated flavonoids, namely delphinidin 3-O-(2-O-(6-O-p-coumaroyl-glucosyl)-6-O-p-coumaroyl-glucoside)-5-O-glucoside (1) and apigenin 7-O-(2-O-glucuronosyl)-glucuronide (2), as two of its main flavonoids. Interestingly, the latter flavone glucuronide (2) caused a bathochromic shift on the anthocyanin (1) toward a blue hue in a dose-dependent manner, showing an intermolecular co-pigment effect. In order to understand the molecular basis for the biosynthesis of this glucuronide, we isolated a cDNA encoding a UDP-dependent glycosyltransferase (UGT88D8), based on the structural similarity to flavonoid 7-O-glucuronosyltransferases (F7GAT) from Lamiales plants. Enzyme assays showed that the recombinant UGT88D8 protein catalyzes the 7-O-glucuronosylation of apigenin and its related flavonoids with preference to UDP-glucuronic acid as a sugar donor. Furthermore, we identified and functionally characterized a cDNA encoding another UGT, UGT94F1, as the anthocyanin 3-O-glucoside2 ''-O-glucosyltransferase (A3Glc2 '' GlcT), according to the structural similarity to sugar-sugar glycosyl-transferases classified to the cluster IV of flavonoid UGTs. Preferential expression of UGT88D8 and UGT94F1 genes in the petals supports the idea that these UGTs play an important role in the biosynthesis of key flavonoids responsible for the development of the blue color of V. persica flowers. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2010.02.008

文献信息

• Color Properties of Four Cyanidin−Pyruvic Acid Adducts
  作者：Joana Oliveira、Virgínia Fernandes、Cándida Miranda、Celestino Santos-Buelga、Artur Silva、Victor de Freitas、Nuno Mateus

  DOI：10.1021/jf061085b

  日期：2006.9.1

  Four anthocyanin-pyruvic adducts were synthesized through the reaction of cyanidin 3-O-glucoside, cyanidin 3-O-rutinoside, cyanidin 3-O-sophoroside, and cyanidin 3-O-sambubioside with pyruvic acid, structurally characterized by liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance (NMR), and their chromatic properties were studied (pH and SO2 stability assays). Overall, these

  通过花青素3-O-葡糖苷，花青素3-O-芸香苷，花青素3-O-槐糖苷和花青素3-O-红景天苷与丙酮酸反应合成了4种花青素-丙酮酸加合物，其结构通过液相色谱-质谱法进行了表征。光谱法（LC-MS）和核磁共振（NMR），以及它们的色性质进行了研究（pH和SO2稳定性测定）。总体而言，这些颜料显示出对pH变色以及在SO2存在下均具有较高的抗变色性，这是由于该发色团对水或亚硫酸氢盐的亲核攻击具有更高的保护作用，从而解释了这种抗变色性。呈无色半缩醛形式。在所有研究的花青素-丙酮酸加合物之间，在针对水和亚硫酸氢盐的亲核攻击的保护中仅发现了微小差异。实际上，与具有芸香糖基或槐糖基部分的类似颜料相比，在黄酮部分的3-O位置上连接有葡萄糖或三糖的花青素-丙酮酸加合物显示具有较小的漂白常数。研究了从CIELAB系统获得的颜料（AD和花青素3-O-葡萄糖苷）的颜色参数，即色度（C），亮度（L）和色相角（h（a，