vitisin A-petunidin-glucoside | 403982-49-0

• 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: vitisin A-petunidin-glucoside
• 英文别名: 5-carboxypyranopetunidin 3-O-β-D-glucopyranoside；5-carboxypyranopetunidin 3-O-β-glucopyranoside；vitisin A of petunidin-3-glucoside；vitisin A-Pt-glu
• CAS: 403982-49-0
• 化学式: C₂₅H₂₃O₁₄
• 分子量: 547.449
• InChiKey: WAHAKFFWGKJQOG-AMKRHLPKSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  39.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  227.13
• 氢给体数：
  8.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  vitisin A-petunidin-glucoside 在 氘代甲醇 作用下， 生成 C₂₅H₂₂⁽²⁾HO₁₄⁽¹⁺⁾
  参考文献：
  名称：

  花色苷和吡喃花色素的反应性。甲醇中芳香族氢-氘交换反应的研究。

  摘要：

  涉及花青素结构及其平衡形式的反应性研究将使人们更好地理解这些抗氧化剂的性质。氢-氘（H-> D）在delphinidin（1），petunidin（2），malvidin（3）的相应部位和羧基吡喃去甲酚苷（4），羧基pyranopetunidin（ 5），在室温下，在纯净CD 3OD和CF 3CO 2D酸化的CD 3OD中，对羧基吡喃酮抗生物素蛋白（6）和黄酮醇槲皮素3-O-（6-α-鼠李糖吡喃糖基-β-吡喃葡萄糖苷）（7）进行了检测。由（1）H NMR积分数据确定的H-6和H-8的H-> D交换常数为2，独立于颜料浓度（最高4 x 10（-2）M）和三氟乙酸酸浓度（0-15％，v / v）。这表明这些反应遵循一级动力学，并且出乎意料地与酸浓度无关。1-3的黄酮阳离子A环的H-6和H-8，以及在相应的半酮形式的氢中，与约100 h（1）和约50 h（2和3）的半衰期交换， 分别。吡喃花色素（4-6）没有发生类似氢的H->

  DOI：

  10.1021/jf071132f
• 作为产物：
  描述：

  矮牵牛素-3-O-葡萄糖 、 丙酮酸 在 potassium hydrogen tartrate buffer 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 生成 vitisin A-petunidin-glucoside
  参考文献：
  名称：

  Antioxidant and Cellular Activities of Anthocyanins and Their Corresponding Vitisins AStudies in Platelets, Monocytes, and Human Endothelial Cells

  摘要：

  During red wine aging, there is a loss of anthocyanins and the formation of various other pigments, so-called vitisins A, which are formed through the chemical interaction of the original anthocyanins with pyruvic acid. The objective of this study was to investigate the antioxidant activities of the most abundant anthocyanins present in red wine (glycosides of delphinidin, petunidin, and malvidin) and their corresponding vitisins A. Anthocyanins exhibited a higher iron reducing as well as 2,2'-azinobis (3-ethyl-benzothiazoline-6-sulfonate) and peroxyl radical scavenging activity than their corresponding vitisins A. Delphinidin showed the highest antioxidant effect of the tested compounds in all of the assays used. Furthermore, we studied the effect of anthocyanins and vitisins A on platelet aggregation and monocyte and endothelial function. Anthocyanins and vitisins did not affect nitric oxide production and tumor necrosis factor-alpha (TNF-alpha) secretion in lipopolysaccharide plus interferon-gamma-activated macrophages. Furthermore, anthocyanins and vitisins did not change collagen-induced platelet aggregation in vitro. However, anthocyanins and to a lesser extent vitisins exhibited protective effects against TNF-alpha-induced monocyte chemoattractant protein production in primary human endothelial cells.

  DOI：

  10.1021/jf035360v

文献信息

• Antioxidant and Cellular Activities of Anthocyanins and Their Corresponding Vitisins AStudies in Platelets, Monocytes, and Human Endothelial Cells
  作者：María García-Alonso、Gerald Rimbach、Julián C. Rivas-Gonzalo、Sonia de Pascual-Teresa

  DOI：10.1021/jf035360v

  日期：2004.6.1

  During red wine aging, there is a loss of anthocyanins and the formation of various other pigments, so-called vitisins A, which are formed through the chemical interaction of the original anthocyanins with pyruvic acid. The objective of this study was to investigate the antioxidant activities of the most abundant anthocyanins present in red wine (glycosides of delphinidin, petunidin, and malvidin) and their corresponding vitisins A. Anthocyanins exhibited a higher iron reducing as well as 2,2'-azinobis (3-ethyl-benzothiazoline-6-sulfonate) and peroxyl radical scavenging activity than their corresponding vitisins A. Delphinidin showed the highest antioxidant effect of the tested compounds in all of the assays used. Furthermore, we studied the effect of anthocyanins and vitisins A on platelet aggregation and monocyte and endothelial function. Anthocyanins and vitisins did not affect nitric oxide production and tumor necrosis factor-alpha (TNF-alpha) secretion in lipopolysaccharide plus interferon-gamma-activated macrophages. Furthermore, anthocyanins and vitisins did not change collagen-induced platelet aggregation in vitro. However, anthocyanins and to a lesser extent vitisins exhibited protective effects against TNF-alpha-induced monocyte chemoattractant protein production in primary human endothelial cells.
• Reactivity of Anthocyanins and Pyranoanthocyanins. Studies on Aromatic Hydrogen–Deuterium Exchange Reactions in Methanol
  作者：Monica Jordheim、Torgils Fossen、Jon Songstad、Øyvind M. Andersen

  DOI：10.1021/jf071132f

  日期：2007.10.1

  hydrogens of the hemiketal forms, exchanged with half-lives of approximately 100 h ( 1) and approximately 50 h ( 2 and 3), respectively. The pyranoanthocyanins (4-6) experienced no H --> D exchange for the analogous hydrogens, but H --> D exchange of H-beta (H-4)(t 1/2 approximately 25 h) for these compounds was observed. Only H-8 underwent significant H --> D exchange in 7. It is concluded that a stabilization

  涉及花青素结构及其平衡形式的反应性研究将使人们更好地理解这些抗氧化剂的性质。氢-氘（H-> D）在delphinidin（1），petunidin（2），malvidin（3）的相应部位和羧基吡喃去甲酚苷（4），羧基pyranopetunidin（ 5），在室温下，在纯净CD 3OD和CF 3CO 2D酸化的CD 3OD中，对羧基吡喃酮抗生物素蛋白（6）和黄酮醇槲皮素3-O-（6-α-鼠李糖吡喃糖基-β-吡喃葡萄糖苷）（7）进行了检测。由（1）H NMR积分数据确定的H-6和H-8的H-> D交换常数为2，独立于颜料浓度（最高4 x 10（-2）M）和三氟乙酸酸浓度（0-15％，v / v）。这表明这些反应遵循一级动力学，并且出乎意料地与酸浓度无关。1-3的黄酮阳离子A环的H-6和H-8，以及在相应的半酮形式的氢中，与约100 h（1）和约50 h（2和3）的半衰期交换， 分别。吡喃花色素（4-6）没有发生类似氢的H->