(2R,3R)-2-[3,4,5-trihydroxy-2-[1-hydroxy-3-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]phenazin-2-yl]phenyl]-3,4-dihydro-2H-chromene-3,5,7-triol

• 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: (2R,3R)-2-[3,4,5-trihydroxy-2-[1-hydroxy-3-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]phenazin-2-yl]phenyl]-3,4-dihydro-2H-chromene-3,5,7-triol
• 化学式: C₃₆H₂₈N₂O₁₂
• 分子量: 680.625
• InChiKey: BPEUWJXBZXTBRD-XXEPNHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  50
• 可旋转键数：
  3
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  247
• 氢给体数：
  10
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (2R,3R)-2-[3,4,5-trihydroxy-2-[1-hydroxy-3-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]phenazin-2-yl]phenyl]-3,4-dihydro-2H-chromene-3,5,7-triol 以 乙醚 、 乙醇 为溶剂， 反应 12.0h， 以9.4 mg的产率得到
  参考文献：
  名称：

  Accumulation of Epigallocatechin Quinone Dimers during Tea Fermentation and Formation of Theasinensins

  摘要：

  Production and accumulation of catechin dimer quinones during tea fermentation were chemically confirmed for the first time by trapping as phenazine derivatives. Direct treatment of the fermented tea leaves with o-phenylenediamine yielded five phenazine derivatives (8-12) of o-quinones of an epigallocatechin dimer and its galloyl esters (13-16), in which two flavan units were linked at the B-rings through a C-C bond. Atrop isomerism of the biphenyl bonds was shown to be the R configuration, suggesting that the o-quinone dimers were generated by stereoselective coupling of monomeric quinones, The total concentration of the phenazine derivatives in the o-phenylenediamine-treated tea leaves was higher than that of theaflavins. In contrast, phenazine derivatives of monomeric quinones of epigallocatechin were not isolated. When the fermented tea leaves were heated, the quinone dimers were converted to theasinensins, which are constituents of black tea, suggesting that theasinensins are generated by reduction of the quinone dimers during the heating and drying steps in black tea manufacturing.

  DOI：

  10.1021/np020245k
• 作为产物：
  描述：

  (-)-表没食子儿茶素 在 Japanese pear homogenate 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 2.5h， 生成 (2R,3R)-2-[3,4,5-trihydroxy-2-[1-hydroxy-3-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]phenazin-2-yl]phenyl]-3,4-dihydro-2H-chromene-3,5,7-triol
  参考文献：
  名称：

  表没食子儿茶素的氧化和苯并二酚酮颜料生产的新机制

  摘要：

  （-）-表没食子儿茶素的酶促氧化产生了两个新的醌二聚体，脱氢theasinensin C和proepitheaflagallin。脱氢茶黄素C具有水合的环己烯酮结构，其氧化还原歧化反应可产生红茶多酚，茶黄素C和E，以及半乳糖基乌龙茶素。基于通过与邻苯二胺缩合制备的喹喔啉衍生物的光谱数据，确定前叶前鞭毛蛋白的结构。加热后将前鞭毛蛋白分解，得到表皮鞭毛蛋白和羟基茶黄素。前者是一种已知的红茶颜料，而后者是一种具有1'，2'，3'-三羟基-3,4-苯并噻吩酮部分的新颜料。结果揭示了由表没食子儿茶素生产这些颜料的新机理。

  DOI：

  10.1016/j.tet.2006.03.021

文献信息

• Enzymatic oxidation of gallocatechin and epigallocatechin: Effects of C-ring configuration on the reaction products
  作者：Yosuke Matsuo、Yuko Yamada、Takashi Tanaka、Isao Kouno

  DOI：10.1016/j.phytochem.2007.08.007

  日期：2008.12

  Tea leaf is rich in pyrogallol-type catechins, and their oxidation is important in the generation of black tea polyphenols. In the present study, the enzymatic oxidation of three pyrogallol-type catechins, (+)- and (-)-gallocatechins and (-)-epigallocatechin, was compared. The reactions yielded unstable quitione products, which were trapped as condensation products with o-phenylenediamine. The oxidation of' (+)-gallocatechin proceeded very slowly compared to the reaction of (-)-epigallocatechiii, and yielded a proepi t hea fl agallin- type dimer as the major product, though oxidation of (-)-epigallocatechin gave predominantly dehydrotheasinensin C. The cis-con figuration of' the C-3 hydroxyl group and the B-ring of (-)-epigallocatechin was apparently crucial for rapid and selective production of dehydrotheasinensin C. Oxidation of (-)-gallocatechin proceeded in a manner similar to that of (+)-gallocatechin, and produced an enantiomer of the (+)-gallocatechin product. The results suggest that enzymes catalyze oxidation of the pyrogallol B-ring to the o-quinone, with subsequent non-enzymatic coupling reactions proceed under highly steric control. (c) 2007 Elsevier Ltd. All rights reserved.
• A new mechanism for oxidation of epigallocatechin and production of benzotropolone pigments
  作者：Yosuke Matsuo、Takashi Tanaka、Isao Kouno

  DOI：10.1016/j.tet.2006.03.021

  日期：2006.5

  Proepitheaflagallin was decomposed on heating to give epitheaflagallin and hydroxytheaflavin. The former is a known black tea pigment and the latter is a new pigment with 1′,2′,3′-trihydroxy-3,4-benzotropolone moiety. The results revealed a new mechanism for the production of these pigments from epigallocatechin.

  （-）-表没食子儿茶素的酶促氧化产生了两个新的醌二聚体，脱氢theasinensin C和proepitheaflagallin。脱氢茶黄素C具有水合的环己烯酮结构，其氧化还原歧化反应可产生红茶多酚，茶黄素C和E，以及半乳糖基乌龙茶素。基于通过与邻苯二胺缩合制备的喹喔啉衍生物的光谱数据，确定前叶前鞭毛蛋白的结构。加热后将前鞭毛蛋白分解，得到表皮鞭毛蛋白和羟基茶黄素。前者是一种已知的红茶颜料，而后者是一种具有1'，2'，3'-三羟基-3,4-苯并噻吩酮部分的新颜料。结果揭示了由表没食子儿茶素生产这些颜料的新机理。
• Accumulation of Epigallocatechin Quinone Dimers during Tea Fermentation and Formation of Theasinensins
  作者：Takashi Tanaka、Chie Mine、Sayaka Watarumi、Toshihiro Fujioka、Kunihide Mihashi、Ying-Jun Zhang、Isao Kouno

  DOI：10.1021/np020245k

  日期：2002.11.1

  Production and accumulation of catechin dimer quinones during tea fermentation were chemically confirmed for the first time by trapping as phenazine derivatives. Direct treatment of the fermented tea leaves with o-phenylenediamine yielded five phenazine derivatives (8-12) of o-quinones of an epigallocatechin dimer and its galloyl esters (13-16), in which two flavan units were linked at the B-rings through a C-C bond. Atrop isomerism of the biphenyl bonds was shown to be the R configuration, suggesting that the o-quinone dimers were generated by stereoselective coupling of monomeric quinones, The total concentration of the phenazine derivatives in the o-phenylenediamine-treated tea leaves was higher than that of theaflavins. In contrast, phenazine derivatives of monomeric quinones of epigallocatechin were not isolated. When the fermented tea leaves were heated, the quinone dimers were converted to theasinensins, which are constituents of black tea, suggesting that theasinensins are generated by reduction of the quinone dimers during the heating and drying steps in black tea manufacturing.