theanaphthoquinone | 302776-47-2

• 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: theanaphthoquinone
• 英文别名: Theanaphthoquinone；8-hydroxy-4,6-bis[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]naphthalene-1,2-dione
• CAS: 302776-47-2
• 化学式: C₂₈H₂₂O₁₁
• 分子量: 534.476
• InChiKey: GWOPGSNHEXOQEQ-TUJIQRHUSA-N

物化性质

• 沸点：
  962.9±65.0 °C(Predicted)
• 密度：
  1.725±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  39
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  194
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  邻苯二胺 、 theanaphthoquinone 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以16.0 mg的产率得到
  参考文献：
  名称：

  Theanaphthoquinone, a novel pigment oxidatively derived from theaflavin during tea-fermentation

  摘要：

  将表儿茶素和表没食子儿茶素与新鲜茶叶或香蕉果提取物处理后，生成了一种名为茶萘醌的新色素。该色素中的1,2-萘醌结构单元是通过氧化途径从茶黄素的苯并环庚烯酮单元衍生而来的。

  DOI：

  10.1039/b003510f
• 作为产物：
  描述：

  茶黄素 在 hydrogen peroxidase 、 horse radish peroxidase 作用下， 以 丙酮 为溶剂， 反应 3.5h， 以35 mg的产率得到theanaphthoquinone
  参考文献：
  名称：

  Stability of Black Tea Polyphenol, Theaflavin, and Identification of Theanaphthoquinone as Its Major Radical Reaction Product

  摘要：

  In the current study, we have focused on isolation and detection of major radical oxidation products from theaflavin in order to better understand antioxidation mechanisms of this compound. Theanaph-thoquinone was identified as a major oxidation product of theaflavin from two different oxidant model systems: DPPH and peroxidase/hydrogen peroxide. This result indicated that the benzotropolone moiety in theaflavin may play an important role in its antioxidant properties. The stability of theaflavin was studied in varying pH solutions: simulated gastric juice and buffer solutions of pH 5.5, pH 7.4, and pH 8.5. The results indicated that theaflavin is unstable in alkaline conditions, while it was stable in acidic conditions. Theanaphthoquinone was identified as an autoxidation product of theaflavin during its stability study in alkaline conditions.

  DOI：

  10.1021/jf050662d

文献信息

• A tandem mass spectrometry method based on selected ions detects low-abundance phenolics in black tea - theatridimensins as products of the oxidative cascade
  作者：Annewieke J. W. Verloop、Jean-Paul Vincken、Harry Gruppen

  DOI：10.1002/rcm.7658

  日期：2016.8.15

  Mixtures of phenolics are widespread in plant‐derived food products, for instance black tea. Detailed compositional analysis of phenolics present is important for quality control. Characterization of low‐abundance compounds often requires extensive purification; hence, the need for rapid screening methods to annotate compounds in complex mixtures without extensive sample preparation. Opportunities

  酚类混合物广泛存在于植物来源的食品中，例如红茶。详细的酚类成分分析对于质量控制很重要。低丰度化合物的表征通常需要大量纯化。因此，需要快速筛选方法来注释复杂混合物中的化合物而无需大量样品制备。以红茶分析为两步氧化产物theatridimensin（T3D）为例，讨论了超高效液相色谱/串联质谱（UHPLC / MS）作为快速筛选方法中工具的机会。
• New degradation mechanism of black tea pigment theaflavin involving condensation with epigallocatechin-3-O-gallate
  作者：Takashi Tanaka、Miho Yasumatsu、Mayu Hirotani、Yosuke Matsuo、Na Li、Hong-Tao Zhu、Yoshinori Saito、Kanji Ishimaru、Ying-Jun Zhang

  DOI：10.1016/j.foodchem.2021.131326

  日期：2022.2

  leaves. In citrate–phosphate buffer solution at pH 6 and room temperature, TNQ reacted nonenzymatically with EGCg to afford three products, whose structures were determined on the basis of spectroscopic data. The results indicated that the double bond of the ortho-naphthoquinone moiety in TNQ reacted with the autoxidation product of EGCg. This study demonstrates novel reactions occurring in the process

  茶萘醌 (TNQ) 是茶黄素的初始和主要氧化产物，茶黄素是一种代表性的红茶色素。然而，在使用光电二极管阵列检测的红茶叶的高效液相色谱分析中几乎没有检测到 TNQ。为了阐明茶黄素在红茶生产过程中的降解机制，本研究调查了TNQ与表没食子儿茶素-3 - O-没食子酸酯 (EGCg)的反应，EGCg 是茶叶中含量最丰富的多酚。在 pH 6 和室温的柠檬酸盐 - 磷酸盐缓冲溶液中，TNQ 与 EGCg 发生非酶促反应，得到三种产物，其结构是根据光谱数据确定的。结果表明，邻位双键TNQ 中的-萘醌部分与 EGCg 的自氧化产物反应。这项研究证明了茶黄素降解过程中发生的新反应，这可能与茶红素的形成有关，茶红素是组成低聚儿茶素氧化产物的主要红茶色素。
• Reaction of the Black Tea Pigment Theaflavin during Enzymatic Oxidation of Tea Catechins
  作者：Yan Li、Akane Shibahara、Yosuke Matsuo、Takashi Tanaka、Isao Kouno

  DOI：10.1021/np900618v

  日期：2010.1.22

  Degradation of the black tea Pigment theaflavin was examined in detail. Enzymatic oxidation of a mixture of epigallocatechin and epicatechin initially produced theaflavin, while prolonged reaction decreased the product. Addition of ethanol to the reaction mixture at the point when theaflavin began to decrease afforded four new products, together with theanaphthoquinone, a known oxidation product of theaflavin. The structures of (he new products were determined by spectroscopic methods. One of the products was an ethanol adduct of a theanaphthoquinone precursor, and this reacted with theaflavin to give two further products. A product generated by coupling of theaflavin with epicatechin quinone was also obtained. The Structures of the products indicate that oxidation and coupling with quinones are key reactions in the degradation of theaflavins. The degradation of theaflavin probably contributes to production of thearubigins.
• Oxidation mechanism of black tea pigment theaflavin by peroxidase
  作者：Rie Kusano、Yosuke Matsuo、Yoshinori Saito、Takashi Tanaka

  DOI：10.1016/j.tetlet.2015.07.037

  日期：2015.9

  A large number of black tea polyphenols remain uncharacterized because of the complexity of catechin oxidation reactions that occur during tea fermentation. In the course of our studies on black tea polyphenols, we examined the enzymatic degradation of theaflavins, which are black tea pigments having a benzotropolone chromophore. Oxidation of theaflavin with peroxidase afforded a new product named theacoumarin A together with known pigment theanaphthoquinone. The structure of the new compound was determined by spectroscopic examination and a production mechanism via theanaphthoquinone is proposed. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of Theaflavin from Epicatechin and Epigallocatechin by Plant Homogenates and Role of Epicatechin Quinone in the Synthesis and Degradation of Theaflavin
  作者：Takashi Tanaka、Chie Mine、Kyoko Inoue、Miyuki Matsuda、Isao Kouno

  DOI：10.1021/jf011301a

  日期：2002.3.1

  Oxidation products of (-)-epicatechin and (-)-epigallocatechin by treatment with homogenates of 62 plants belonging to 49 families were compared, Forty-six plants were capable of synthesizing theaflavin, a black tea pigment, regardless of whether they contained catechins. Loquat, Japanese pear, and blueberry had activities higher than that of fresh tea leaves after 5 h of treatment; furthermore, these plants oxidized theaflavin to theanaphthoquinone. An additional new metabolite, dehydrotheasinensin, was generated on treatment with fresh tea leaves, eggplant, and unripened Japanese orange. Evidence for the oxidation of epigallocatechin and theaflavin by electron transfer to epicatechin quinone was demonstrated in a time course study using bananas and trapping the quinone intermediates as glutathione conjugates.