Analysis of stereochemistry and biosynthesis of epicatechin in tea plants by chiral phase high performance liquid chromatography

被引:14
作者
Qian, Yumei [1 ,2 ]
Zhao, Xianqian [3 ]
Zhao, Lei [4 ]
Cui, Lilan [1 ]
Liu, Li [1 ]
Jiang, Xiaolan [1 ]
Liu, Yajun [3 ]
Gao, Liping [3 ]
Xia, Tao [1 ]
机构
[1] Anhui Agr Univ, State Key Lab Tea Plant Biol & Utilizat, Hefei 230036, Anhui, Peoples R China
[2] Suzhou Univ, Sch Biol & Food Engn, Suzhou 234000, Anhui, Peoples R China
[3] Anhui Agr Univ, Sch Life Sci, Hefei 230036, Anhui, Peoples R China
[4] Qjngdao Agr Univ, Coll Hort, Qingdao Key Lab Genet Improvement & Breeding Hort, Qingdao 266109, Shandong, Peoples R China
来源
JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES | 2015年 / 1006卷
关键词
High performance liquid chromatography; Chiral phase; Stereochemistry; Biosynthesis; Epicatechin; Teaw; ANTHOCYANIDIN-REDUCTASE; CAMELLIA-SINENSIS; EPIMERASE ACTIVITY; CATECHINS; PROANTHOCYANIDINS; MODEL; (+)-CATECHIN; FLAVAN-3-OLS; DEGRADATION; POLYPHENOLS;
D O I
10.1016/j.jchromb.2015.10.024
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Tea (Camellia sinensis) is rich in flavan-3-ols (catechins), especially epicatechin (EC), which is the predominant extension unit of polymeric proanthocyanidins (PAs). However, studies assessing EC's sterechemistry are scarce. Here, a high performance liquid chromatography column using amylose tris-(3, 5-dimethylphenylcarbamate) immobilized on silica-gel as chiral stationary phases (CSPs) was applied to explore its stereochemistry and biosynthetic pathway in tea plants. The results revealed (-)-epicatechin [(-)-EC] was the predominant di-hyroxy-non-galloylated-catechins, while (+)-epicatechin [(+)-EC] was not detected. Interestingly, (-)-EC was the only product obtained from cyanidin using the partially purified native C. sinensis anthocyanidin reductase (CsANR) in the presence of reduction nicotinamide adenine dinucleotide phosphate (NADPH); meanwhile, (+)-EC was the main product using recombinant CsANR in the same conditions. In addition, (-)-EC could be obtained from (+)-catechin [(+)-C] using recombinant CsANR, which displayed C-3-epimerase activity in the presence of oxidation nicotinamide adenine dinucleotide phosphate (NADP(+)). But the partially purified native CsANR did not possess this function. Finally, (-)-EC could result from the de-gallate acid reaction of epicatechin gallate (ECG) catalyzed by a novel partially purified, native galloylated catechins hydrolase (GCH) from tea leaves. In summary, (-)EC is likely the product of native protein from the tea plants, and (+)-EC is only produced in a reaction catalyzed by recombinant CsANR in vitro. (C) 2015 The Authors. Published by Elsevier B.V.
引用
收藏
页码:1 / 7
页数:7
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