theasinensin C | 1236228-58-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: theasinensin C
• 英文别名: theasinensin E；theasinesin C；theasinesin E；(2R,3R)-2-[3,4,5-trihydroxy-2-[2,3,4-trihydroxy-6-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]phenyl]phenyl]-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 1236228-58-2
• 化学式: C₃₀H₂₆O₁₄
• 分子量: 610.528
• InChiKey: JPBGHWKYWUEIOT-XYTTVBAYSA-N

物化性质

• 沸点：
  1020.9±65.0 °C(Predicted)
• 密度：
  1.811±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  44
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  261
• 氢给体数：
  12
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  theasinensin C 以 水 为溶剂， 反应 0.5h， 以15.9%的产率得到isotheasinensin E
  参考文献：
  名称：

  儿茶素的酶促氧化产物结构

  摘要：

  要了解未鉴定的红茶多酚的结构的氧化产物（ - ） -儿茶素进行了调查。酶促氧化时，可以得到四个新的氧化产物（反应混合物的后续加热6，和9 - 11与theasinensins C（沿）4）和E（5），dehydrotheasinensin E（12），epitheaflagallin，hydroxytheaflavin，和desgalloyl oolongtheanin。进行化学和光谱确定的新化合物的结构。Isotheasinensin E（6）是一个C-2差向异构体5和化合物9和10是氧化产物12。另一个新的化合物，11，是黄色颜料和推定为proepitheaflagallin的降解产物。结果披露红茶生产过程中出现的新的氧化机制。

  DOI：

  10.1016/j.tet.2013.07.045
• 作为产物：
  描述：

  theasinensin A 在 单宁酶 作用下， 以 水 为溶剂， 反应 1.0h， 以12 mg的产率得到没食子酸
  参考文献：
  名称：

  Nonaka, Gen-Ichiro; Kawahara, Osamu; Nishioka, Itsuo, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 11, p. 3906 - 3914

  摘要：

  DOI：

文献信息

• 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。
• Tannins and Related Compounds. CXIV. Structures of Novel Fermentation Products, Theogallinin, Theaflavonin and Desgalloyl Theaflavonin from Black Tea, and Changes of Tea Leaf Polyphenols during Fermentation.
  作者：Fumio HASHIMOTO、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.40.1383

  日期：——

  Continuing chemical examination of black tea has led to the isolation of three novel fermentation products, theogallinin (1), theaflavonin (10) and desgalloyl theaflavonin (11). The structure of 1 was established on the basis of physico-chemical evidence to be a condensation product linked through pyrogallol-pyrogallol rings in theogallin (2) and (-)-epigallocatechin 3-O-gallate (3), while 10 and 11 were characterized as B, B'-linked bisflavonoids formed by an oxidative coupling of isomyricitrin (12) and tea catechins [3 and (-)-epigallocatechin (4)]. Furthermore, high performance liquid chromatography analyses of the changes of tea polyphenols during fermentation have revealed that original tea catechins are more rapidly transformed by endogenous phenol oxidase to theasinensins (e.g.6, 8) and oolongtheanin (13) than the formerly known black tea pigments, theafiavins.

  在对红茶进行持续的化学检测中，成功分离出了三种新的发酵产物：茶黄素（1）、茶黄酮（10）和去没食子酰茶黄酮（11）。通过物理化学证据确定，1的结构是一种缩合产物，连接着邻苯三酚环和来自茶黄素（2）和（-）表没食子儿茶素3-O-没食子酸酯（3）的没食子酸环，而10和11则被鉴定为通过异鼠李素（12）和茶儿茶素[3和（-）表没食子儿茶素（4）]的氧化偶联形成的B，B'-连接的双黄酮。此外，高效液相色谱分析揭示了在发酵过程中，原始茶儿茶素被内源性酚氧化酶更快地转化为茶氨酸（例如6、8）和乌龙茶素（13），而非之前已知的红茶色素茶黄素。
• Hashimoto, Fumio; Nonaka, Gen-Ichiro; Nishioka, Itsuo, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 5, p. 1676 - 1684
  作者：Hashimoto, Fumio、Nonaka, Gen-Ichiro、Nishioka, Itsuo

  DOI：——

  日期：——
• 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.
• Production and degradation mechanism of theacitrin C, a black tea pigment derived from epigallocatechin-3-O-gallate via a bicyclo[3.2.1]octane-type intermediate
  作者：Yosuke Matsuo、Yan Li、Sayaka Watarumi、Takashi Tanaka、Isao Kouno

  DOI：10.1016/j.tet.2011.01.058

  日期：2011.3

  Black tea is rich in polyphenols and has been shown to have various health benefits: however, its components have not yet been clarified in detail. Enzymatic oxidation of epigallocatechin-3-O-gallate, the most abundant polyphenol in tea, is thought to contribute significantly to the production of black tea polyphenols. We identified theacitrin C, an unstable black tea pigment, as an enzymatic oxidation product of epigallocatechin-3-O-gallate. Degradation of theacitrin C afforded theacitrinin A and 2,3,5,7-tetrahydroxychroman-3-O-gallate. Furthermore, theacitrinin B, which was isolated from black tea, is deduced to be a degradation product of theacitrin A, the desgalloyl analogue of theacitrin C. The structures of theacitrinins A and B were elucidated based on spectroscopic data. This is the first time that a degradation product of theacitrin has been isolated from black tea. We also examined the influence of esterification of the epigallocatechin C-3 hydroxyl group on the decomposition of bicyclo[3.2.1]octane-type intermediates. (C) 2011 Elsevier Ltd. All rights reserved.