cyanidin 3-O-(2-O-β-D-xylopyranosyl)-β-D-glucopyranoside | 63535-17-1

• 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-xylopyranosyl)-β-D-glucopyranoside
• 英文别名: cyanidin 3-O-[2-O-(β-xylopyranosyl)-β-glucopyranoside]；cyanidin 3-O-β-D-sambubioside；cyanidin-3-O-(2''-xylosyl)-glucoside；cyanidin 3-sambubioside-5-glucoside；cyanidin 3-xylosylgalactoside；cyanidin 3-O-sambubioside；Cyanidin 3-O-beta-D-sambubioside；(2S,3R,4S,5R)-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]oxyoxane-3,4,5-triol
• CAS: 63535-17-1
• 化学式: C₂₆H₂₉O₁₅
• 分子量: 581.507
• InChiKey: ZPPQIOUITZSYAO-AOBOYTTNSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -1.15
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  240
• 氢给体数：
  10
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  cyanidin 3-O-(2-O-β-D-xylopyranosyl)-β-D-glucopyranoside 、 丙酮酸 以 水 为溶剂， 反应 120.0h， 生成
  参考文献：
  名称：

  四种花青素-丙酮酸加合物的颜色性质。

  摘要：

  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，

  DOI：

  10.1021/jf061085b
• 作为产物：
  描述：

  cyanidin 3-O-[2-O-(β-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-β-glucopyranosyl)-trans-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside] 在 水 、 sodium hydroxide 作用下， 生成 阿魏酸 、 丙二酸 、 cyanidin 3-O-(2-O-β-D-xylopyranosyl)-β-D-glucopyranoside 、 1-O-p-hydroxycinnamoyl-β-D-glucopyranose
  参考文献：
  名称：

  Acylated cyanidin glycosides from the pale-violet flowers of Ionopsidium acaule (Desf.) Rchb. (Brassicaceae)

  摘要：

  Three new acylated cyanidin 3-sambubioside-5-glucosides (1-3) and one new acylated cyanidin 3-(3(X)-glucosylsambubioside)-5-glucoside (4) were isolated from the pale-violet flowers of Ionopsidium acaule (Desf.) Rch beta, together with one known anthocyanin. These new pigments were determined by chemical and spectroscopic methods to be cyanidin 3-O-[2-O-(beta-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-beta- glucopyranosyl)-trans-p-coumaroyl)-b-glucopyranoside]-5-O-[6-O-(malonyl)-b-glucopyranoside] (1), cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-beta-xylopyranosyl)-6-O-(4-O-(beta-glucopyranosyl)-trans-pcoumaroyl)-beta-glucopyranoside]-5-O-[6-O-(malonyl)-b-glucopyranoside] (2), cyanidin 3-O-[2-O-(2-O( trans-feruloyl)-beta-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-beta-glucopyranosyl)-trans-p-coumaroyl)- b-glucopyranoside]-5-O-[6-O-(malonyl)-beta-glucopyranoside] (3) and cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-3-O-(beta-glucopyranosyl)-beta-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-b-glucopyranosyl)- trans-p-coumaroyl)-beta-glucopyranoside]-5-O-[6-O-(malonyl)-beta-glucopyranoside] (4). These polyacylated cyanidin glycosides are responsible for the pale-violet flower color of I. acaule, and the contribution of the number of hydroxycinnamic acid residues to the bluing effect was discussed. (C) 2013 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.phytol.2013.10.004

文献信息

• 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。
• Adiponectin expression promoter
  申请人：Tsuda Takanori

  公开号：US20060234957A1

  公开（公告）日：2006-10-19

  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。
• Acylated pelargonidin and cyanidin 3-sambubiosides from the flowers of Aeschynanthus species and cultivars
  作者：Tsukasa Iwashina、Sri Rahayu、Kohtaro Sugahara、Takayuki Mizuno、Chie Tsutsumi、Didik Widyatmoko

  DOI：10.1016/j.phytochem.2021.112956

  日期：2021.12
• 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，
• Acylated cyanidin glycosides from the pale-violet flowers of Ionopsidium acaule (Desf.) Rchb. (Brassicaceae)
  作者：Fumi Tatsuzawa、Narumi Takahashi、Kazuhisa Kato、Koichi Shinoda、Norio Saito、Toshio Honda

  DOI：10.1016/j.phytol.2013.10.004

  日期：2014.2

  Three new acylated cyanidin 3-sambubioside-5-glucosides (1-3) and one new acylated cyanidin 3-(3(X)-glucosylsambubioside)-5-glucoside (4) were isolated from the pale-violet flowers of Ionopsidium acaule (Desf.) Rch beta, together with one known anthocyanin. These new pigments were determined by chemical and spectroscopic methods to be cyanidin 3-O-[2-O-(beta-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-beta- glucopyranosyl)-trans-p-coumaroyl)-b-glucopyranoside]-5-O-[6-O-(malonyl)-b-glucopyranoside] (1), cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-beta-xylopyranosyl)-6-O-(4-O-(beta-glucopyranosyl)-trans-pcoumaroyl)-beta-glucopyranoside]-5-O-[6-O-(malonyl)-b-glucopyranoside] (2), cyanidin 3-O-[2-O-(2-O( trans-feruloyl)-beta-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-beta-glucopyranosyl)-trans-p-coumaroyl)- b-glucopyranoside]-5-O-[6-O-(malonyl)-beta-glucopyranoside] (3) and cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-3-O-(beta-glucopyranosyl)-beta-xylopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-b-glucopyranosyl)- trans-p-coumaroyl)-beta-glucopyranoside]-5-O-[6-O-(malonyl)-beta-glucopyranoside] (4). These polyacylated cyanidin glycosides are responsible for the pale-violet flower color of I. acaule, and the contribution of the number of hydroxycinnamic acid residues to the bluing effect was discussed. (C) 2013 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.