Frontier Orbitals and Аctive Site of Тea Рolyphenol Мolecules Epigallocatechin Gallate and Gallocatechin Gallate

2021 ◽  
Vol 95 (9) ◽  
pp. 1857-1863
Author(s):  
Tianyu Tang ◽  
Jiancheng Yu ◽  
Li Yuan ◽  
Limin Lu ◽  
Yanlin Tang
2004 ◽  
Vol 48 (1) ◽  
pp. 69-74 ◽  
Author(s):  
Cristina Paveto ◽  
María C. Güida ◽  
Mónica I. Esteva ◽  
Virginia Martino ◽  
Jorge Coussio ◽  
...  

ABSTRACT The trypanocidal action of green tea catechins against two different developmental stages of Trypanosoma cruzi is reported for the first time. This activity was assayed with the nonproliferative bloodstream trypomastigote and with the intracellular replicative amastigote parasite forms. An ethyl acetate fraction from Camellia sinensis green tea leaves, which contains most of the polyphenolic compounds and the maximal trypanocidal activity, was obtained by fractionation of the aqueous extract with organic solvents. The active compounds present in this extract were further purified by LH-20 column chromatography and were identified by high-performance liquid chromatography analysis with a photo diode array detector and gas chromatography coupled to mass spectroscopy. The following flavan-3-ols derivatives, known as catechins, were identified: catechin, epicatechin, gallocatechin, epigallocatechin, catechin gallate, epicatechin gallate, gallocatechin gallate, and epigallocatechin gallate. The purified compounds lysed more than 50% of the parasites present in the blood of infected BALB/c mice at concentrations as low as 0.12 to 85 pM. The most active compounds were gallocatechin gallate and epigallocatechin gallate, with minimal bactericidal concentrations that inhibited 50% of isolates tested of 0.12 and 0.53 pM, respectively. The number of amastigotes in infected Vero cells decreased by 50% in the presence of each of these compounds at 100 nM. The effects of the catechins on the recombinant T. cruzi arginine kinase, a key enzyme in the energy metabolism of the parasite, were assayed. The activity of this enzyme was inhibited by about 50% by nanomolar concentrations of catechin gallate or gallocatechin gallate, whereas the other members of the group were less effective. On the basis of these results, we suggest that these compounds could be used to sterilize blood and, eventually, as therapeutic agents for Chagas' disease.


2012 ◽  
Vol 22 (7) ◽  
pp. 3372-3378 ◽  
Author(s):  
Lianwu Xie ◽  
Yaping Guo ◽  
Bo Cai ◽  
Jing Yang

Molecules ◽  
2019 ◽  
Vol 24 (6) ◽  
pp. 1185
Author(s):  
Zeyi Ai ◽  
Shuyuan Liu ◽  
Fengfeng Qu ◽  
Haojie Zhang ◽  
Yuqiong Chen ◽  
...  

The transcellular transport and metabolism of eight green tea catechins (GTCs) were studied in Caco-2 monolayers, with the aim of investigating the effect of cis–trans isomerism on the membrane permeability and biotransformation of GTCs. The results showed that the catechin stereochemistry significantly affects the efflux transport rather than the absorption transport in the Caco-2 monolayers. The trans catechins showed a better transcellular permeability than their corresponding cis (epi) catechins in the efflux transport, as the efflux amount of trans catechins were all significantly higher than that of the cis (epi) catechins at each concentration and each time point tested. Moreover, the relative contents of the (+)-catechin (C)-O-sulfate, (+)-gallocatechin (GC)-O-sulfate, (−)-catechin gallate (CG)-O-sulfate, and (−)-gallocatechin gallate (GCG)-O-sulfate in the efflux transport were 2.67, 16.08, 50.48, and 31.54 times higher than that of the (−)-epicatechin (EC)-O-sulfate, (−)-epigallocatechin (EGC)-O-sulfate, (−)-epicatechin gallate (ECG)-O-sulfate, and (−)-epigallocatechin gallate (EGCG)-O-sulfate, respectively. It indicated that more metabolites were observed after the transcellular efflux of trans catechins. Furthermore, after two hours of incubation, the GTCs could significantly increase the expression of multidrug resistance-associated protein 2 (MRP2) and breast cancer-resistance protein (BCRP), and decrease the expression of P-glycoprotein in the Caco-2 cells. The regulation of GTCs on P-glycoprotein, MRP2, and BCRP could also be significantly influenced by the chemical and dimensional structure. In a conclusion, catechin stereochemistry significantly affects the transport and metabolism of GTCs when refluxed in the Caco-2 monolayers.


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