miraxanthin V | 5375-64-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: miraxanthin V
• 英文别名: (2S,4E)-4-[2-[2-(3,4-dihydroxyphenyl)ethylimino]ethylidene]-2,3-dihydro-1H-pyridine-2,6-dicarboxylic acid
• CAS: 5375-64-4
• 化学式: C₁₇H₁₈N₂O₆
• 分子量: 346.34
• InChiKey: PDKFHZWVCCZUIF-DJDUWTSMSA-N

物化性质

• 沸点：
  677.1±55.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  139
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  盐酸多巴胺 、 (2S,4E)-1,2,3,4-四氢-4-(2-氧代乙亚基)吡啶-2,6-二甲酸 以 甲醇 为溶剂， 生成 miraxanthin V
  参考文献：
  名称：

  重组DOPA 4,5-双加氧酶体外合成甜菜黄素及其自由基清除活性的评价

  摘要：

  使用重组Mirabilis jalapa从1-二羟基苯丙氨酸（L-DOPA）大规模酶促合成了虾青素的发色团β-丙二酸。DOPA 4,5-二加氧酶。合成后，将脯氨酸直接添加到浓缩的反应混合物中以生成脯氨酸-甜菜黄素。纯化产物的分子量和核磁共振谱与先前报道的脯氨酸-甜菜黄素的分子量和核磁共振谱相同。通过纯化的铍金属与氨基酸或胺的缩合反应合成了二十四种虾青素。建立了用于鉴定不同虾青素种类的HPLC方案。在大规模条件下，制备了脯氨酸，多巴胺和γ-氨基丁酸（GABA）-甜菜黄素作为代表性的虾青素，并将它们的1,1-二苯基-2-吡啶并肼基自由基清除活性与已知的抗氧化剂进行了比较。GABA-甜菜黄素显示相对较低的活性，而多巴胺-甜菜黄素的活性与红色素甜菜碱和花青素花青素3-葡糖苷相似。脯氨酸-β-黄嘌呤具有三种合成化合物中最高的活性，与类黄酮槲皮素相似。

  DOI：

  10.1021/jf1030086

文献信息

• The Role of Phenolic Hydroxy Groups in the Free Radical Scavenging Activity of Betalains
  作者：Fernando Gandía-Herrero、Josefa Escribano、Francisco García-Carmona

  DOI：10.1021/np900131r

  日期：2009.6.26

  Free radical scavenging compounds play important roles as health-protecting factors. Betalains are natural water-soluble pigments present in most plant families belonging to the order Caryophyllales. They are the subject of increasing attention following the discovery of their antiradical capacity, but a systematic analysis of the structural features involved in the activity is necessary. In this paper, both natural and previously unconsidered betaxanthins were obtained in order to study the role of phenolic hydroxy groups in the high free radical scavenging activity of betalains. Pigments were characterized spectrophotometrically, chromatographically, and by ESI-MS, and their antiradical and antioxidant properties were studied under the ABTS(center dot+) radical and FRAP assays. A high intrinsic activity is described that is not linked to the presence of hydroxy groups or aromaticity in the pigment structure. In addition, the presence of phenolic hydroxy groups implies an enhancement of the antiradical activity, reaching a TEAC value in the ABTS(center dot+) assay of 5.8 +/- 0.2 for the pure compound with two hydroxy groups.
• In Vitro Synthesis of Betaxanthins Using Recombinant DOPA 4,5-Dioxygenase and Evaluation of Their Radical-Scavenging Activities
  作者：Hiroshi Sekiguchi、Yoshihiro Ozeki、Nobuhiro Sasaki

  DOI：10.1021/jf1030086

  日期：2010.12.8

  for proline-betaxanthin. Twenty-four betaxanthin species were synthesized by the condensation reaction of purified betalamic acid and amino acids or amines. An HPLC protocol was established for identifying the different betaxanthin species. Proline-, dopamine-, and γ-aminobutyric acid (GABA)-betaxanthins were prepared as representative betaxanthins under large-scale conditions, and their 1,1-diphe

  使用重组Mirabilis jalapa从1-二羟基苯丙氨酸（L-DOPA）大规模酶促合成了虾青素的发色团β-丙二酸。DOPA 4,5-二加氧酶。合成后，将脯氨酸直接添加到浓缩的反应混合物中以生成脯氨酸-甜菜黄素。纯化产物的分子量和核磁共振谱与先前报道的脯氨酸-甜菜黄素的分子量和核磁共振谱相同。通过纯化的铍金属与氨基酸或胺的缩合反应合成了二十四种虾青素。建立了用于鉴定不同虾青素种类的HPLC方案。在大规模条件下，制备了脯氨酸，多巴胺和γ-氨基丁酸（GABA）-甜菜黄素作为代表性的虾青素，并将它们的1,1-二苯基-2-吡啶并肼基自由基清除活性与已知的抗氧化剂进行了比较。GABA-甜菜黄素显示相对较低的活性，而多巴胺-甜菜黄素的活性与红色素甜菜碱和花青素花青素3-葡糖苷相似。脯氨酸-β-黄嘌呤具有三种合成化合物中最高的活性，与类黄酮槲皮素相似。