Preparation method of epicatechin gallate

Introduction

Tea is a drink that two-thirds of the world's people choose to consume. It can be divided into three kinds: green tea, black tea and oolong tea. Studies have shown that green tea extract catechins can synergistically enhance cell apoptosis, gene expression and anti-cancer efficacy with a variety of anti-cancer drugs. Epicatechin achyrate (ECG) is a major component of green tea, which can prevent and treat cancer, cardiovascular disease It is well known that only free drugs can reach the target to exert biological activity through passive diffusion, and the free concentration of drugs depends on the degree of protein binding.

Picture 1 Epicatechin achyrate powders

Preparation method of epicatechin gallate

The invention discloses a preparation method of epicatechin gallate. The method comprises the steps of (1) taking crude tea polyphenol, dissolving the crude tea polyphenol and obtaining a tea polyphenol solution; (2) subjecting the tea polyphenol solution to a AB-8 type macroporous resin column, eluting, extracting with ethyl acetate, and collecting an organic layer; (3) drying the obtained organic layer in the step (2), dissolving, subjecting the obtained organic layer to a D101 macroporous resin column, eluting, extracting with ethyl acetate and collecting the organic layer; (4) drying the obtained organic layer, dissolving, crystallizing, filtering and drying to obtain the epicatechin gallate. According to the technical scheme of the invention, the AB-8 type macroporous resin column and the D101 macroporous resin column are adopted for the two-step chromatography process. In this way, the finally obtained epicatechin gallate (ECG) is high in yield. Meanwhile, the purity of the ECG is over 99%.[1]

Epicatechin gallate serves as a novel new delhi metallo-β-lactamase-1 (NDM-1) inhibitor

The natural product is thought to be a big reservoir for medicinal compounds. (–)-Epicatechin gallate (ECG), the third major catechin extracted from green tea, possesses a series of pharmacological functions, such as anti-oxidation, anticancer, anti-inflammatory, anti-apoptosis, anti-obesity, and neuroprotection. We have previously constructed a high-throughput screening model for NDM-1 and found ECG as a potent NDM-1 inhibitor. To the best of our knowledge, it has not been reported on inhibition of β-lactamases before. Therefore, in this article, we aimed to reveal the inhibitory efficacy and the probable action mechanism of ECG on NDM-1 to acquire a novel inhibitor of NDM-1.

The β-lactam antibiotic resistance caused by NDM-1 has become a major crisis of global public health. We have previously screened out epicatechin gallate (ECG) as a potent NDM-1 inhibitor. We further discussed its inhibitory effect and action mode in the present study. According to our results, ECG reversibly inactivated NDM-1 in a non-competitive mode, with an IC50 value of 4.48 μM. ECG effectively recovered the activity of several β-lactam antibiotics against resistant strain harboring blaNDM-1. Especially, the effects on carbapenems were worth mentioning. The zinc supplement assay indicated a zinc-related mechanism of ECG. Different from traditional chelating agents, it showed low toxicity both in vivo and in vitro. In a word, our findings provided a promising NDM-1 inhibitor, ECG, which was able to assist carbapenems against NDM-1-producing strain[2].

Application of epicatechin achyrate in cancer

At present, cancer has become the number one killer threatening human health, and cancer treatment mostly adopts comprehensive means[3]. In addition to surgery, radiotherapy, immunotherapy and traditional Chinese medicine treatment, chemotherapy has been paid more and more attention because of its emphasis on systemic treatment and its therapeutic effect on advanced cancer that has spread and metastasized. However, the toxicity and drug resistance of anti-tumor drugs are serious problems of tumor chemotherapy, Many drugs are limited in dosage due to their strong toxic and side effects.

5-Fluorouracil (FU) It is a pyrimidine antimetabolic drug widely used in the process of chemical treatment of cancer. 5 - Fluorouracil is a pyrimidine antimetabolic drug widely used in the process of chemical treatment of cancer. It also has the problem of high toxicity and drug resistance in the process of cancer treatment. In order to increase the efficacy, reduce the toxicity and side effects, and delay the occurrence of drug resistance, Combined drug use has become the primary strategy for cancer treatment in clinic. Human serum albumin (HSA) is the most abundant protein in plasma, accounting for nearly 60% of the total protein. The crystal structure shows that HSA is composed of 585 amino acids, It includes three structurally similar domains (I-III), and each domain can be divided into two subfields (A and B) Therefore, the interaction between epicatechin gallate (EGG) and HSA is conducive to understanding the mechanism of drug efficacy in vivo, and provides a theoretical basis for improving the anticancer activity of drugs and reducing toxic side effects. 

Reference

1 Preparation method of epicatechin gallate, CN106380457A (B) ? 2017-02-08 ? JIANGSU TIANSHENG PHARMACEUTICAL CO LTD)

2 Wang Qian, Liu Chennan, Han Jiangxue, Liu Sihan, Xiao Chunling, Guan Yan, Li Xinghua, Wang Ying, Wang Xiao, Meng Jianzhou, Gan Maoluo, Liu Yishuang. A new NDM-1 inhibitor: (–) - epicatechin gallate [J] Journal of Chinese Pharmaceutical Sciences,2021,30(09):716-724

3 Yuan Lixia, Liu Min. Thermodynamic study on the effect of epicatechin gallate on the binding of 5-fluorouracil with human serum albumin [J]. Journal of Liaocheng University (Natural Science Edition), 2018, 31 (02): 15-20

You may like