vitisin A | 388089-38-1

• 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: vitisin A
• 英文别名: 5-carboxypyranomalvidin 3-O-β-D-glucopyranoside；5-carboxypyranomalvidin 3-O-β-glucopyranoside；carboxypyranomalvidin-3-O-β-D-glucoside；10-carboxypyranomalvidin 3-glucoside；5-carboxypyranomalvidin-3-glucoside；carboxypyranomalvidin-3-glucoside；vitisin A of malvidin-3-glucoside
• CAS: 388089-38-1
• 化学式: C₂₆H₂₅O₁₄
• 分子量: 561.476
• InChiKey: QVULQDHVHOUFCX-AQFMKAHKSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  0.81
• 重原子数：
  40.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  216.13
• 氢给体数：
  7.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  vitisin A 在 氘代甲醇 作用下， 生成
  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：

  锦葵素-3-O-葡萄糖苷 、 sodium pyruvate 在 potassium bitartrate 、 酒石酸 作用下， 以 乙醇 为溶剂， 反应 1008000.0h， 生成 vitisin A
  参考文献：
  名称：

  Vitisin A Content in Chilean Wines from Vitis vinifera Cv. Cabernet Sauvignon and Contribution to the Color of Aged Red Wines

  摘要：

  Vitisin A was prepared from malvidin 3-glucoside and pyruvic acid in model wine medium, isolated by countercurrent chromatography, and purified by preparative high-performance liquid chromatography (HPLC). The synthesized compound was used as a reference standard to quantify vitisin A in Chilean wines from Vitis vinifera cv. Cabernet Sauvignon, including a vertical row of wines from the same vineyard over 16 years. Maximum vitisin A content was reached within the first year of storage. Importantly, up to half of the initial amount of vitisin A in young wines was still present in 15 year old wines. Although vitisin A was found to be much more stable as compared to other monomeric C-4 underivatized anthocyanins, it also slowly degrades after reaching its peak concentration. The "color activity concept" was applied to vitisin A, malvidin 3-glucoside, malvidin 3-(6"-acetylglucoside), and polymeric pigments isolated by countercurrent chromatography in order to estimate their contribution toward the overall color expression of wines. It was found that vitisin A is only a minor contributor to the visually perceived color of aged red wines (color contribution similar to 5%). The major contributor is the polymeric fraction (color contribution similar to 70-90%).

  DOI：

  10.1021/jf0346612

文献信息

• Synthesis and structural characterization by LC–MS and NMR of a new semi-natural blue amino-based pyranoanthocyanin compound
  作者：Joana Oliveira、Ana Fernandes、Victor de Freitas

  DOI：10.1016/j.tetlet.2016.02.026

  日期：2016.3

  The synthesis and structural characterization by LC–MS and NMR of a new blue amino-based pyranoanthocyanin-derived pigment is presented from the reaction of A-type vitisin and 4-(dimethylamino)-cinnamic acid. The structure of the new compound is similar to portisin B being the hydroxyl and or methoxyl groups from the cinnamyl moiety substituted by a dimethylamino group. The presence of this amino group

  通过A型葡萄红素和4-（二甲基氨基）-肉桂酸的反应，提出了一种新的基于蓝色氨基基吡喃花青素的颜料的LC-MS和NMR合成与结构表征。该新化合物的结构类似于门童B，其是来自肉桂基部分的羟基和/或甲氧基被二甲基氨基取代。该氨基的存在是导致广泛的π离域的原因，因此，这些新的半天然颜料呈现出强烈的蓝色。
• Pyranoanthocyanin Dimers: A New Family of Turquoise Blue Anthocyanin-Derived Pigments Found in Port Wine
  作者：Joana Oliveira、Joana Azevedo、Artur M. S. Silva、Natércia Teixeira、Luis Cruz、Nuno Mateus、Victor de Freitas

  DOI：10.1021/jf9044414

  日期：2010.4.28

  found to occur in aged Port wines and respective sediments (lees). The data obtained revealed two new families of compounds with unique spectroscopic characteristics, displaying a wavelength of the maximum absorption at high wavelength in the visible spectrum at ∼730 and ∼680 nm. The structure of these pigments was elucidated by liquid chromatography/diode array detector−mass spectrometry (LC/DAD−MS) and

  在目前的工作中，已发现几种具有相似光谱特征的化合物出现在陈年的波特酒和各自的沉积物（酒糟）中。获得的数据揭示了两个具有独特光谱特征的化合物新家族，它们在〜730和〜680 nm的可见光谱中显示了在高波长下最大吸收的波长。通过液相色谱/二极管阵列检测器质谱（LC / DAD-MS）和核磁共振（NMR）阐明了这些色素的结构，并建立了它们在葡萄酒中的形成途径。它们的结构由通过亚甲基桥连接在一起的两个吡喃花色素苷部分组成。这个新的化合物家族在酸性条件下显示出诱人且稀有的绿松石蓝色，并且从未在文献中进行报道。
• Preparation of 10-(hexylcarbamoyl)pyranomalvidin-3-glucoside from 10-carboxypyranomalvidin-3-glucoside using carbodiimide chemistry
  作者：Marta Monteiro、Ivo E. Sampaio-Dias、Nuno Mateus、Victor de Freitas、Luís Cruz

  DOI：10.1016/j.foodchem.2022.133429

  日期：2022.11

  affinity into liposoluble formulations and enhance their unique physicochemical and biological properties. In this work, 10-carboxypyranomalvidin-3-glucoside was functionalized with hexylamine via carbodiimide chemistry compatible with the absence of hydroxyl protecting groups. A new amide conjugate attached to an alkyl chain with better hydrophobic features was obtained and isolated from its precursor. Mass

  花青素和吡喃花青素是替代合成色素的有吸引力的天然色素。然而，由于不稳定性和溶解性问题，花青素的亲脂化过程已成为一种有价值且有效的策略，可将其稳定性和亲和力扩展到脂溶性制剂中，并增强其独特的物理化学和生物学特性。在这项工作中，10-carboxypyranomalvidin-3-glucoside 通过与不存在羟基保护基团兼容的碳二亚胺化学与己胺功能化。获得了连接到具有更好疏水特性的烷基链上的新酰胺共轭物，并从其前体中分离出来。质谱、FTIR、和 NMR 光谱证实亲脂化位点发生在羧基上，并且由 UV-Vis 测定的辛醇-水分配系数显示其对非极性介质具有优异的亲和力。总体而言，我们首次报道了一种新的吡喃花青素亲脂性衍生物，这鼓励了对这类新型化合物的进一步研究，以将其纳入基于脂质的食品和化妆品配方中。
• Reaction between Hydroxycinnamic Acids and Anthocyanin−Pyruvic Acid Adducts Yielding New Portisins
  作者：Joana Oliveira、Victor de Freitas、Artur M. S. Silva、Nuno Mateus

  DOI：10.1021/jf070968f

  日期：2007.7.1

  Three new anthocyanin-derived pigments were found to occur in a 2-year-old Port red wine. Their structures were elucidated through LC/DAD-MS and NMR analysis and were found to correspond to a pyranoanthocyanin moiety linked to substituted cinnamyl substituents. The structures of these compounds are very similar to the one already reported for portisins, with a phenolic moiety replacing the catechin moiety. The newly formed anthocyanin-derived compounds display a bathochromic shift of the lambda(max) (similar to 540 nm) when compared with their anthocyanin-pyruvic acid adduct precursor (lambda(max) = 511 nm), which may be due to the extended conjugation of the pi electrons in the structures of those pigments. Studies performed in model solutions helped to clarify the formation mechanism of these pigments that can result from the nucleophilic attack of the olefinic double bond of a hydroxycinnamic acid to the eletrophilic C-10 position of the anthocyanin-pyruvic acid adduct, followed by the loss of a formic acid molecule and decarboxylation. The chromatic characterization of these malvidin-3-glucoside-derived compounds revealed a higher resistance to discoloration against the nucleophilic attack by water and bisulfite when compared to malvidin-3-glucoside that is almost converted into its colorless hemiacetal form. However, the resistance to discoloration of these new pigments is not as high as the one reported for catechin-derived portisins. This could be explained by the presence of a smaller group (hydroxycinnamyl group), which does not protect so efficiently the chromophore against nucleophilic attack at the C-2 position. The occurrence of these pigments in red wine highlights new chemical pathways involving anthocyanin-pyruvic acid derivatives as precursors for the formation of new pigments in subsequent stages of wine aging that may contribute to its color evolution.
• 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.