cyanidin 3-sophoroside-5-glucoside | 47888-56-2

• 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-sophoroside-5-glucoside
• 英文别名: Cyanidin 3-sophoroside-5-glucoside；(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 47888-56-2
• 化学式: C₃₃H₄₁O₂₁
• 分子量: 773.676
• InChiKey: LOXRHOFBKUTJEZ-FEFFISETSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -4.32
• 重原子数：
  54
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  340
• 氢给体数：
  14
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  cyanidin 3-sophoroside-5-glucoside 以 aq. phosphate buffer 为溶剂， 反应 24.0h， 生成 原儿茶酸
  参考文献：
  名称：

  在温和的中性溶液中酰化花色苷的去向

  摘要：

  在中性溶液中，被羟基肉桂酸酰化的花色苷与它们的非酰化同系物相比，通常呈现出诱人的蓝色和更高的抗色差性。但是，它们仍然容易受到氧化反应和水解反应的了解不足，而氧化反应和水解反应强烈地导致颜色损失并限制了其工业应用。在这项工作中，通过UPLC-DAD-MS（高分辨率和高分辨率）研究了分离的红甘蓝花色苷（0、1或2个酰基）在pH 7下的热降解。观察到非氧化性变化，包括脱酰基和分子内酰基转移，发现它们很大程度上取决于酰基的数量和位置以及铁离子的存在。在中度和高级热降解下，有几种氧化机理被证明可导致原儿茶酸，间苯二甲醛2-O-葡糖苷，酰基糖苷和2,4,6-三羟基苯基乙酸和3,5,7-三羟基香豆素的衍生物。根据观察到的产品分布和添加铁的影响2+离子和H 2 O 2，讨论了可能的降解机理。它们可能以从阴离子碱（中性溶液中的主要有色形式）到O 2的一或两个电子转移开始。然后产生的过氧化氢可以作为亲电子体与

  DOI：

  10.1016/j.dyepig.2020.108326
• 作为产物：
  描述：

  3-O-(6-O-(E-p-coumaryl)-2-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl)-5-O-(β-D-glucopyranosyl)cyanidin 以 aq. phosphate buffer 为溶剂， 反应 24.0h， 以14%的产率得到cyanidin 3-sophoroside-5-glucoside
  参考文献：
  名称：

  在温和的中性溶液中酰化花色苷的去向

  摘要：

  在中性溶液中，被羟基肉桂酸酰化的花色苷与它们的非酰化同系物相比，通常呈现出诱人的蓝色和更高的抗色差性。但是，它们仍然容易受到氧化反应和水解反应的了解不足，而氧化反应和水解反应强烈地导致颜色损失并限制了其工业应用。在这项工作中，通过UPLC-DAD-MS（高分辨率和高分辨率）研究了分离的红甘蓝花色苷（0、1或2个酰基）在pH 7下的热降解。观察到非氧化性变化，包括脱酰基和分子内酰基转移，发现它们很大程度上取决于酰基的数量和位置以及铁离子的存在。在中度和高级热降解下，有几种氧化机理被证明可导致原儿茶酸，间苯二甲醛2-O-葡糖苷，酰基糖苷和2,4,6-三羟基苯基乙酸和3,5,7-三羟基香豆素的衍生物。根据观察到的产品分布和添加铁的影响2+离子和H 2 O 2，讨论了可能的降解机理。它们可能以从阴离子碱（中性溶液中的主要有色形式）到O 2的一或两个电子转移开始。然后产生的过氧化氢可以作为亲电子体与

  DOI：

  10.1016/j.dyepig.2020.108326

文献信息

• Triacylated anthocyanins from Ajuga reptans flowers and cell cultures
  作者：Norihiko Terahara、Alfons Callebaut、Riichiro Ohba、Tadahiro Nagata、Mayumi Ohnishi-Kameyama、Masahiro Suzuki

  DOI：10.1016/0031-9422(95)00838-1

  日期：1996.5

  anthocyanins were isolated from Ajuga reptans flowers and one from the cell cultures. By FAB mass spectrometry measurements, the structures of these pigments were determined as delphinidin and cyanidin glucosides acylated with two cinnamic acids, while three of them were also malonylated. A delphinidin-based pigment in the crude extract from cell cultures was identical to the major flower pigment as shown by

  从 Ajuga reptans 花中分离出四种花青素，从细胞培养物中分离出一种。通过 FAB 质谱测量，这些色素的结构被确定为飞燕草素和花青素糖苷被两种肉桂酸酰化，而其中三种也被丙二酰化。如 HPLC 共色谱所示，来自细胞培养物的粗提取物中的翠雀素类色素与主要的花色素相同。此外，应用由 DQF-COSY、NOESY、ROESY、2D-HOHAHA、HSQC 和 HMBC 组成的 1H 和 13C NMR 方法，确定了两种新花青素的结构为飞燕草素和花青素 3-O-(2-O-( 6-O-(E)-对香豆基-β-D-吡喃葡萄糖基)-(6-O-(E)-对香豆基)-β-D-吡喃葡萄糖基)-5-O-(6-O-丙二酰) -β-D-吡喃葡萄糖苷）。
• ADIPONECTIN EXPRESSION PROMOTER
  申请人：SAN-EI GEN F.F.I., INC.

  公开号：EP1602652A1

  公开（公告）日：2005-12-07

  To prevent or alleviate various pathologies caused by lifestyle-related diseases, etc., the present invention provides a substance having an effect of promoting the expression and elevating the expression level of adiponectin, and applications thereof. An adiponectin expression promoting agent containing, as an active ingredient, at least one cyanidin compound selected from the group consisting of cyanidin and cyanidin glycosides can be applied to pharmaceutical or food compositions for use in applications in which the pharmacological effects of adiponectin are utilized.

  为了预防或缓解与生活方式有关的疾病等引起的各种病症，本发明提供了一种具有促进脂肪连通素表达和提高其表达水平效果的物质及其应用。一种含有至少一种选自由青花苷和青花苷糖苷组成的组中的青花苷化合物作为活性成分的促脂肪生成素表达剂可应用于药物或食品组合物中，以用于利用脂肪生成素的药理作用的应用中。
• A tetra-acylated cyanidin 3-sophoroside-5-glucoside from the purple-violet flowers of Moricandia arvensis (L.) DC. (Brassicaceae)
  作者：Fumi Tatsuzawa、Shun Ito、Motoki Sato、Hiroki Muraoka、Kazuhisa Kato、Yoshihito Takahata、Satoshi Ogawa

  DOI：10.1016/j.phytol.2012.12.007

  日期：2013.5

  A novel tetra-acylated cyanidin 3-sophoroside-5-glucoside was isolated from the purple-violet flowers of Moricandia arvensis (L.) DC. (Family: Brassicaceae), and determined to be cyanidin 3-O-[2-O-(2-O-(4-O-(6-O-(4-O-(beta-glucopyranosyl)-trans-caffeoyl)-beta-glucopyranosyl)-trans-caffeoyl)-beta-glucopyranosyl)-6-O-(trans-caffeoyl)-beta-glucopyranoside]-5-O-[ 6-O-(malonyl)-beta-glucopyranoside] by chemical and spectroscopic methods. (C) 2013 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.
• Tetra-acylated cyanidin 3-sophoroside-5-glucosides from the flowers of Iberis umbellata L. (Cruciferae)
  作者：Norio Saito、Fumi Tatsuzawa、Eri Suenaga、Kenjiro Toki、Koichi Shinoda、Atsushi Shigihara、Toshio Honda

  DOI：10.1016/j.phytochem.2008.04.010

  日期：2008.12

  The structures of 11 acylated cyanidin 3-sophoroside-5-glucosides (pigments 1-11), isolated from the flowers of Iberis umbellata cultivars (Cruciferae), were elucidated by chemical and spectroscopic methods. Pigments 1-11 were acylated with malonic acid, p-coumaric acid, ferulic acid, sinapic acid and/or glucosylhydroxycinnamic acids.Pigments 1-11 were classified into four groups by the substitution patterns of the linear acylated residues at the 3-position of the cyanidin. In the first group, pigments 1-3 were determined to be cyanidin 3-O-[2-O-(2-O-(acyl)-beta-glucopyranosyl)-6-O-(trans-p-coumaroyl)-p-glucopyranoside]-5-O-[6-O-(malonyl)-beta-glucopyranoside], in which the acyl moiety varied with none for pigment 1, ferulic acid for pigment 2 and sinapic acid for pigment 3. In the second one, pigments 4-6 were cyaniclin 3-O-[2-O-(2-O-(acyl)-beta-glucopyranosyl)-6-O-(4-O-(beta-glucopyranosyl)-trans-p-coumaroyl)-p-glucopyranosidel-5-O-[6-O-(malonyl)-p-glucopyranosidel, in which the acyl moiety varied with none for pigment 4, ferulic acid for pigment 5 and sinapic acid for pigment 6. In the third one, pigments 7-9 were cyanidin 3-O-[2-O-(2-O-(acyl)-beta-glucopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-p-glucopyranosyl)-trans-p-coumaroyl)-p-glucopyranosidel-5- 0-[6-0-(j-nalonyl)-p-glucopyranosidel, in which the acyl moiety varied with none for pigment 7, ferulic acid for pigment 8, and smapic acid for pigment 9. In the last one, pigments 10 and 11 were cyanidin 3-O-[2-O-(2-O-(acyl)-beta-glucopyranosyl)-6-O-(4-O-(6-O-(4-O-(beta-glucopyranosyl)-trans-feruloyl)-beta-glucopyranosyl)-trans-p-coumaroyl)-beta-glucopyranoside]-5-O-[6-O-(malo nyl)-p-glucopyranosidel, in which acyl moieties were none for pigment 10 and ferulic acid for pigment 11.The distribution of these pigments was examined in the flowers of four cultivars oft umbellatabyHPLC analysis. Pigment 1 acylated with one molecule ofp-coumaric acid was dominantly observed in purpleviolet cultivars. On theotherhand, pignients(9 and 11)acylated with three moleCUlesot'hydroxychinamic acids were observed in lilac (purple-violet) cultivars as major anthocyanins. The bluing effect and stability on these anthocyanin colors were discussed in relation to the molecular number ofhydroxycinnamic acids in these anthocyanin molecules. (c) 2008 Elsevier Ltd. All rights reserved.
• The fate of acylated anthocyanins in mildly heated neutral solution
  作者：Julie-Anne Fenger、Rebecca J. Robbins、Thomas M. Collins、Olivier Dangles

  DOI：10.1016/j.dyepig.2020.108326

  日期：2020.7

  anthocyanins (0, 1 or 2 acyl groups) at pH 7 was investigated by UPLC-DAD-MS (low- and high-resolution). Non-oxidative alterations, including deacylation and intramolecular acyl transfer, were observed and found very dependent on the number and position of the acyl group(s) as well as on the presence of iron ions. At intermediate and advanced thermal degradation, several oxidative mechanisms were evidenced

  在中性溶液中，被羟基肉桂酸酰化的花色苷与它们的非酰化同系物相比，通常呈现出诱人的蓝色和更高的抗色差性。但是，它们仍然容易受到氧化反应和水解反应的了解不足，而氧化反应和水解反应强烈地导致颜色损失并限制了其工业应用。在这项工作中，通过UPLC-DAD-MS（高分辨率和高分辨率）研究了分离的红甘蓝花色苷（0、1或2个酰基）在pH 7下的热降解。观察到非氧化性变化，包括脱酰基和分子内酰基转移，发现它们很大程度上取决于酰基的数量和位置以及铁离子的存在。在中度和高级热降解下，有几种氧化机理被证明可导致原儿茶酸，间苯二甲醛2-O-葡糖苷，酰基糖苷和2,4,6-三羟基苯基乙酸和3,5,7-三羟基香豆素的衍生物。根据观察到的产品分布和添加铁的影响2+离子和H 2 O 2，讨论了可能的降解机理。它们可能以从阴离子碱（中性溶液中的主要有色形式）到O 2的一或两个电子转移开始。然后产生的过氧化氢可以作为亲电子体与