Novel Theaflavin-Type Chlorogenic Acid Derivatives Identified in Black Tea,Journal of Agricultural and Food Chemistry

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Novel Theaflavin-Type Chlorogenic Acid Derivatives Identified in Black Tea
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2018-03-13 00:00:00 , DOI: 10.1021/acs.jafc.7b06044
Shuwei Zhang ₁ , Chun Yang _{1,

2} , Emmaneul Idehen ₁ , Lei Shi _{1,

2} , Lishuang Lv ₃ , Shengmin Sang ₁

Affiliation

Consumption of black tea contributed to many health benefits including the prevention of heart disease and certain types of cancer. However, the chemical composition of black tea has not been fully explored. Most studies have examined different interactions between the four major tea catechins, and limited studies have investigated the interaction between catechins and other components in tea. In the present study, we tested our hypothesis that the ortho-dihydroxyl structure of chlorogenic acid (CGA) could react with the vic-trihydroxy structure of (−)-epigallocatechin 3-gallate (EGCG) and (−)-epigallocatechin (EGC) to generate theaflavin-type of compounds during black tea fermentation. The reaction between CGA and EGCG or EGC was catalyzed by horseradish peroxidase (POD) in the presence of H₂O₂. Two theaflavin-type compounds EGCG-CGA and EGC-CGA were purified using a Sephadex LH-20 column. Their structures were elucidated on the basis of the analysis of their MS and 1D- and 2D-NMR spectroscopic data. Furthermore, the existence of these two novel compounds was characterized by LC/MS/MS analysis. We also found that EGCG-CGA and EGC-CGA had very similar inhibitory effects on the growth of human colon cancer cells with that of theaflavin 3,3′-digallate. These findings shed light on the interactions between the major bioactive compounds, catechins, and other minor compounds in tea. The confirmation of the presence of this type of reaction in black tea may provide more understanding of the complexity of black tea chemistry.

中文翻译：

红茶中鉴定的新型茶黄素型绿原酸衍生物

食用红茶有助于许多健康益处，包括预防心脏病和某些类型的癌症。然而，红茶的化学成分尚未得到充分研究。大多数研究都研究了四种主要茶儿茶素之间的不同相互作用，而有限的研究则研究了儿茶素与茶中其他成分之间的相互作用。在本研究中，我们检验了以下假设：绿原酸（CGA）的邻-二羟基结构可与vic反应（-）-表没食子儿茶素3-没食子酸酯（EGCG）和（-）-表没食子儿茶素（EGC）的-三羟基结构在茶发酵过程中产生茶黄素型化合物。在H ₂ O ₂存在下，辣根过氧化物酶（POD）催化CGA与EGCG或EGC之间的反应。使用Sephadex LH-20色谱柱纯化两种茶黄素类化合物EGCG-CGA和EGC-CGA。根据其质谱以及1D-和2D-NMR光谱数据的分析，阐明了它们的结构。此外，通过LC / MS / MS分析表征了这两种新型化合物的存在。我们还发现，EGCG-CGA和EGC-CGA与茶黄素3,3'-digallate对人结肠癌细胞的生长具有非常相似的抑制作用。这些发现揭示了茶中主要生物活性化合物，儿茶素和其他次要化合物之间的相互作用。红茶中这种类型反应的存在的确认可以提供对红茶化学的复杂性的更多理解。

更新日期：2018-03-13

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