1257-08-5 Usage
Uses
Used in Pharmaceutical Applications:
(-)-Epicatechin gallate is used as a potent antioxidant for modulating a wide range of membrane proteins. Its bilayer-modifying potency was tested using gramicidin A (gA) channels as probes, demonstrating its ability to alter gA channel function and modify bilayer properties.
Used in Antimicrobial Applications:
(-)-Epicatechin gallate is used as an adjunct treatment for methicillin-resistant bacteria, specifically methicillin-resistant strains of S. aureus. The hydroxyl groups of ECG contribute to its potent antioxidant activity and facilitate the killing of these resistant strains.
Used in Food and Beverage Industry:
(-)-Epicatechin gallate is used as a natural polyphenol in green and black teas, contributing to their antioxidant properties and potential health benefits.
Used in Research and Development:
(-)-Epicatechin gallate is used in the development of novel drug delivery systems to enhance its applications and efficacy against cancer cells. Various organic and metallic nanoparticles have been employed as carriers for ECG delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes.
Active ingredients of the Tea Polyphenol
Epicatechin gallate briefly referred to as EGCG, being the ester formed by epigallocatechin and gallate acid, belonging to a kind of tea polyphenols; is a kind of flavonoids, D-form ester catechins.
Epicatechin gallate is the cathchin monomer isolated from the tea, being the major active ingredients of polyphenols.
Figure 1 shows the stereochemical structure of epicatechin gallate
Tea polyphenols
Tea polyphenols are the general term of the tea polyphenols, being a kind of polyphenols using catechins as the major body with biological oxidation effect. Chinese tea usually contains 20% to 30% tea polyphenols. Tea polyphenols can be divided into five categories, of which the flavanol (mainly catechins) is the most important; besides there are also anthocyanins, flavonoids, flavonols and phenolic acids. Catechins account for about 50% to 70% of the total amount of tea polyphenols, accounting for 12% to 24% of the dry weight of tea. It is a compound of complex structure, including four kinds of simple catechins (also called non-esters type catechins) and two kinds of complex catechins (also known as ester type catechins). The trend of the content of tea polyphenols is generally as below: green tea is higher than black tea; summer and autumn tea are more than spring tea. The main pharmacological effects of tea polyphenols are:
(1) Lower the blood lipid, inhibit atherosclerosis. (2) Enhance the capillaries, lower blood sugar. (3) Anti-radiation. (4) Anti-aging. (5) Anti-cancer and anti-mutation. (6) Bactericidal effect.
Figure 2 is the tea polyphenols containing the major chemical substances;
Biological activity
Oral biological activity is poor; the efficacy of taking a dosage of 800 mg is actually an order of magnitude lower than the real situation.
Toxicity
EGCG might be carcinogenic; study has found that during pregnancy, intake of polyphenols will increase the risk of neonatal leukemia; it is not good for pregnant women to uptake bioflavones; during pregnancy, administration of tea or coffee during pregnancy may increase the risk for children of suffering from malignant tumor of central nervous system (CNS), and the specific mechanism remains unknown.
Biosynthesis pathway of Epicatechin gallate
Figure 3 shows the synthesis of Epicatechin gallate in plants.
Enzymes involved in the synthesis pathway include phenylalanine ammonialyase (PAL), cinnamate 4-hydroxylase (C4H), 4-?coumaroyl?CoA ligase (4CL), chalcone isomerase (CHI), chalcone synthase (CHS), flavonoid3’?hydroxylase (F3’H),flavonoid3’, 5’?hydroxylase (F3’5’H), (2S)?flavanone 3?hydroxylase (F3H), dihydroflavonol-4-?reductase (DFR), leucoanthocyanidin reductase (LAR), anthocyanidin reductase，ANR、anthocyanidin synthase (ANS) and UDPG? flavonoid glucosyl transferase UFGT and so on.
Antibacterial effect
Epicatechin gallate has antibacterial effect, having varied bacteriostatic and bactericidal effect against many kinds of common pathogens including Proteus, Staphylococcus aureus, Staphylococcus epidermidis; Streptococcus, Botox, Lactobacillus and Vibrio cholera, especially intestinal pathogens. Moreover, epicatechin gallate can also effectively prevent the infection of antibiotic-resistant staphylococcus; it has inhibitory effect against hemolysin ECG and EGCG. In addition, it also has inhibitory effect against pathogenic fungi that can cause human skin disease, such as the head tinea alba, plaque blister white ringworm, sweat bubble white ringworm and stubborn tinea and other parasitic fungi.
Anti-oxidization effect
Epicatechin gallate belongs to a polyphenol hydroxyl chemical, and is quite easily to be oxidized into esters and provide proton H, thus having significant antioxidant property. The antioxidant capacity of tea polyphenols is 18 times than that of vitamin E; 3 to 10 times than that of vitamin C. It has the ability to block the synthesis of N-nitroso compounds, inhibit the activity of lipoxygenase and lipid peroxidation. This makes it play excellent disease prevention and treatment effect in the anti-cancer, anti-mutation, anti-aging, prevention and treatment of cardiovascular disease, treatment of hepatitis and many other aspects.
Other pharmacological effects
Hypoglycemic effect, a number of experimental data have confirmed that tea polyphenols is an invertase inhibitor, so it can inhibit the conversion of sucrose to glucose, leading to the decrease of the blood sugar.
Antiviral effect, it has inhibitory effect against influenza A, influenza B virus as well as the human respiratory system covariate virus (RSV). In addition, tea polyphenols also have a strong anti-inhibitoryeffect against gastroenteritis virus, hepatitis A virus and plant viruses. In recent years, it has been confirmed that tea polyphenol is a strong novel inhibitor of HIV-IRT.
Anti-cancer, anti-mutation effect; epicatechin gallate not only inhibits a variety of chemical carcinogen-induced mutations, but also inhibit the mutagenic effect of some kinds of mixed carcinogens (tobacco fog thickener, coal tar, smoked fish extract, X Ray).
For the treatment of cardiovascular disease; studies have shown that tea polyphenols have various effects including anticoagulant, promote fibrinolysis, anti-platelet aggregation, lowering blood pressure, lowering blood pressure, prevention and treatment of atherosclerosis as well as protecting the myocardium.
Anti-allergic and anti-inflammatory effect, tea polyphenols has a significant inhibitory effect on the transparent enzyme, among which theaflavin gallate has an inhibitory activity of 99.1%, being able to effectively inhibit the rapid allergic reaction.
Gastrointestinal protection function. It can inhibit the H-K-ATPase in the gastric mucosa, which fundamentally inhibits the secretion of gastric acid. This reduces the gastric irritation and injury by gastric acid. It can treat ulcers and alleviate the gastrointestinal spasm as well.
Storage
It should be sealed, placed in a cool dry environment, to be avoided of moisture, light and high temperature.
Biological Activity
(-)-epicatechin gallate is a major catechin component in green tea [1].(-)-epicatechin gallate (ecg) plays an important role in cell growth inhibition, apoptosis and membrane transport system [1].(-)-epicatechin gallate is a kind of catechin. in hct-116 cells, ecg activated transcription factor 3 (atf3), which played a critical role in pro-apoptosis. egr-1 was involved in ecg-induced atf3 expression. in hct-116 cells, ecg (50 μm) increased nag-1 and atf3 expression in time- and dose-dependent way [1]. in carcinoma hsc-2 cells, ecg (50 μm) exhibited cytotoxicity with midpoint cytotoxicity (nr50) value of 67 μm. however, in normal hgf-2 fibroblasts, ecg exhibited cytotoxicity at concentrations up to 25 μm with nr50 value of 100 μm. in carcinoma hsc-2 cells, ecg (250 μm) induced nucleosomal dna fragmentation and apoptosis. ecg (150 μm) significantly increased caspase-3 activity [2].in rats, there were five metabolites of ecg: (-)-epicatechin gallate, 3’,4’’-di-o-methyl-(-)-epicatechin gallate, 4’’-o-methyl-(-)-epicatechin gallate, 4’-o-methyl-(-)-epicatechin gallate and 3’-o-methyl-(-)-epicatechin gallate, which were excreted in rat urine [3].
Biochem/physiol Actions
(?)-Epicatechin gallate (ECG), a potent free-radical scavenger has an inhibitory effect on collagenase and elastase enzymes making it an anti-aging agent. It displays antiproliferative effects on human colorectal cells and hence is a chemo-preventative agent. It influences cell survival, preventing apoptosis or autophagy by promoting cell proliferation in oxygen-glucose deprived human brain microvascular endothelial cells. Being structurally and functionally similar to EGCG, ECG might be involved in balancing the mammalian target of rapamycin (mTOR)-AMP-activated protein kinase (AMPK) pathways in endoplasmic reticulum stress. It prevents cell death in this scenario by showing resistance against oxygen-deprived cells. ECG may contribute in preventing oxidative stress. It effectively inhibits secretory sphingomyelinase in many disease states and provides protection for human spermatozoa in Assisted reproductive technology (ART).
references
[1]. cho kn, sukhthankar m, lee sh, et al. green tea catechin (-)-epicatechin gallate induces tumour suppressor protein atf3 via egr-1 activation. eur j cancer, 2007, 43(16): 2404-2412. [2]. babich h, krupka me, nissim ha, et al. differential in vitro cytotoxicity of (-)-epicatechin gallate (ecg) to cancer and normal cells from the human oral cavity. toxicol in vitro, 2005, 19(2): 231-242.[3]. kohri t, suzuki m, nanjo f. identification of metabolites of (-)-epicatechin gallate and their metabolic fate in the rat. j agric food chem, 2003, 51(18): 5561-5566.
Check Digit Verification of cas no
The CAS Registry Mumber 1257-08-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,2,5 and 7 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1257-08:
(6*1)+(5*2)+(4*5)+(3*7)+(2*0)+(1*8)=65
65 % 10 = 5
So 1257-08-5 is a valid CAS Registry Number.
InChI:InChI=1/C22H18O10/c23-11-6-18-12(8-17(28)21(31-18)9-1-2-13(24)14(25)3-9)19(7-11)32-22(30)10-4-15(26)20(29)16(27)5-10/h1-7,17,21,23-29H,8H2/t17-,21+/m0/s1
1257-08-5Relevant articles and documents
Study on in Vitro Preparation and Taste Properties of N-Ethyl-2-Pyrrolidinone-Substituted Flavan-3-Ols
Han, Zisheng,Ho, Chi-Tang,Jiang, Zongde,Lai, Guoping,Qin, Chunyin,Wan, Xiaochun,Wen, Mingchun,Zhai, Xiaoting,Zhang, Hui,Zhang, Liang
, (2022/04/07)
N-ethyl-2-pyrrolidinone-substituted flavan-3-ols (EPSFs) were prepared by an in vitro model reaction, and the taste thresholds of EPSFs and their dose-over-threshold factors in large-leaf yellow tea (LYT) were investigated. The effects of initial reactant
Molecular Mechanism by Which Tea Catechins Decrease the Micellar Solubility of Cholesterol
Sakakibara, Takumi,Sawada, Yoshiharu,Wang, Jilite,Nagaoka, Satoshi,Yanase, Emiko
, (2019/07/03)
Tea polyphenols lower the levels of cholesterol in the blood by decreasing the cholesterol micellar solubility. To clarify this mechanism, the interactions between taurocholic acid and (-)-epigallocatechin gallate (EGCg) and its derivatives were investigated. 13C NMR studies revealed remarkable chemical-shift changes for the carbonyl carbon atom and the 1″- and 4″-positions in the galloyl moiety. Furthermore, 1H NMR studies using (-)-EGCg derivatives showed that the number of hydroxyl groups on the B ring did not affect these interactions, whereas the carbonyl carbon atom and the aromatic ring of the galloyl moiety had remarkable effects. The configuration at the 2- and 3-positions of the catechin also influenced these interactions, with the trans-configuration resulting in stronger inhibition activity than the cis-configuration. Additionally, a 1:1 component ratio for the catechin-taurocholic acid complex was determined by electrospray ionization-mass spectrometry. These molecular mechanisms contribute to the development of cholesterol-absorption inhibitors.
METHODS OF TREATING COGNITIVE AND BEHAVIORAL IMPAIRMENT IN DOWN SYNDROME AND ALZHEIMERS DISEASE PATIENTS
-
, (2018/09/24)
The present invention relates to methods of treating cognitive and behavioral impairment in Down syndrome and/or Alzheimer's disease patients, Alzheimer's disease, neurodegenerative disease, cancer, DYRK1A-mediated disorders and methods of modulating and inhibiting DYRK1-A comprising use of catechins.
Potential O-acyl-substituted (-)-epicatechin gallate prodrugs as inhibitors of DMBA/TPA-induced squamous cell carcinoma of skin in swiss albino mice
Vyas, Sandeep,Manon, Benu,Vir Singh, Tej,Dev Sharma, Pritam,Sharma, Manu
experimental part, p. 599 - 613 (2011/11/12)
(-)-Epicatechin-3-gallate (1) is one of the principal catechins of green tea and exhibits cancer-preventive activities in various animal models. However, this compound is unstable in neutral or alkaline medium and, therefore, has a poor bioavailability. To improve its stability, O-acyl derivatives of 1 were prepared by isolating the partially purified tea catechin fraction from green tea extract and treating it with a variety of acylating agents. The resulting derivatives, compounds 2-6, were screened for their antitumor potential against 7,12-dimethylbenz[a]anthracene (DMBA)/12-O-tetradecanoylphorbol-13-acetate (TPA)-induced squamous cell carcinogenesis of skin in mice. The results showed that the antitumor activity decreased with the increase in size of the chain length of the acyl groups, i.e., from compound 2, derivative with an Ac group, to compound 6, possessing a valeryl group. Moreover, the C4 derivative with a branched acyl chain, 5, had a lower activity than the linear C4 derivative 4. This reduction in the inhibitory activity may be due to the steric hindrance by the two Me groups. Moreover, significant increases in the protein levels analyzed by ELISA of c-Jun, p65, and p53 were observed in the skin of DMBA/TPA treated mice, whereas mice treated with 2 and DMBA/TPA had a similar expression of these transcription factors than the control mice. The prodrug potential of the O-acyl derivatives 2-6 showed that they were adequately stable to be absorbed intact from the intestine, more stable at gastric pH, and suitable for oral administration. Copyright
New oligomeric proanthocyanidin glycosides platanoside-A and platanoside-B from Platanus orientalis trunk bark
Nishanbaev,Khidyrova,Vdovin,Abdullaev,Shakhidoyatov,Aripov
experimental part, p. 357 - 362 (2010/10/03)
Two new oligomeric proanthocyanidin glycosides were isolated from trunk bark of Platanus orientalis. Their structures and relative configurations were found to be 7-O-β-D-Glcp-(-)-epicatechin-(4β-8)-(-)- epicatechin(4β-8)-(-)-epicatechin-3-O-gallate (plat
General synthesis of epi-series catechins and their 3-gallates: Reverse polarity strategy
Ohmori, Ken,Yano, Takahisa,Suzuki, Keisuke
supporting information; experimental part, p. 2693 - 2696 (2010/08/21)
A general synthetic route to the epi-series catechins was developed based on the reverse polarity strategy. Aromatic nucleophilic substitution reaction followed by the sulfinyl-metal exchange and cyclization enabled stereo-controlled access to various members of epi-series catechins and their 3-gallates.
Study of the green tea polyphenols catechin-3-gallate (CG) and epicatechin-3-gallate (ECG) as proteasome inhibitors
Wan, Sheng Biao,Chen, Di,Dou, Q. Ping,Chan, Tak Hang
, p. 3521 - 3527 (2007/10/03)
The green tea polyphenol catechin-3-gallate (CG) and epicatechin-3-gallate (ECG) were synthesized enantioselectively via a Sharpless hydroxylation reaction followed by a diastereoselective cyclization. Their potencies to inhibit the proteasome activity were measured. The unnatural enantiomers were found to be equally potent to the natural compounds.
Stereoselective synthesis of procyanidin B3-3-O-gallate and 3,3″-di-O-gallate, and their abilities as antioxidant and DNA polymerase inhibitor
Saito, Akiko,Emoto, Mana,Tanaka, Akira,Doi, Yuki,Shoji, Kazuaki,Mizushina, Yoshiyuki,Ikawa, Hiroshi,Yoshida, Hiromi,Matsuura, Nobuyasu,Nakajima, Noriyuki
, p. 12043 - 12049 (2007/10/03)
A simple method for the synthesis of procyanidin B3 substituted with a galloyl group at the 3 and 3″ position is described. Condensation of a benzylated catechin-3-O-gallate electrophile with a nucleophile, catechin and catechin-3-O-gallate, proceeded smoothly and stereoselectively to afford the corresponding dimer gallates, procyanidin B3-3-O-gallate and procyanidin B3-3,3″-di-O-gallate, in good yields. Further, their antioxidant activities on UV-induced lipid peroxide formation, DPPH radical scavenging activity and inhibitory activity of DNA polymerase were also investigated. Among three procyanidin B3 congeners (procyanidin B3, 3-O-gallate and 3,3″-di-O-gallate), the 3,3″-di-O-gallate derivative showed the strongest antioxidant and radical scavenging activity. Interestingly, the 3-O-gallate derivative was the strongest inhibitor of mammalian DNA polymerase α with IC50 value of 0.26 μM, although it showed the weakest antioxidant and radical scavenging activity. It became apparent that the presence of a galloyl group at the C-3 position in the proanthocyanidin oligomer was very important for biological activity, however, the antioxidant activity of these compounds was not parallel to the DNA polymerase inhibitory activity. Graphical Abstract
Cysteinyl-flavan-3-ol conjugates from grape procyanidins. Antioxidant and antiproliferative properties.
Torres,Lozano,Julia,Sanchez-Baeza,Anglada,Centelles,Cascante
, p. 2497 - 2509 (2007/10/03)
New bio-based antioxidant compounds have been obtained by depolymerisation of grape polymeric flavanols in the presence of cysteine. Their preparation and purification, as well as their antiradical/antioxidant and antiproliferative properties are reported
Oligomeric proanthocyanidin glycosides of Clementsia semenovii
Matamarova,Kuliev,Vdovin,Abdullaev,Murzubraimov
, p. 676 - 682 (2007/10/03)
Five new proanthocyanidins have been isolated from the roots of Clementsia semenovii A. Bor. The structures of two of these compounds have been established by various chemical and physical methods: 7-0-[6-0-galloyl-β-D-Glcp →6 O-βD-Glcp →6O-β-D-Glcp → 6O-β-D-Glcp]-(+)-gallocatechin-(4α-8)-(+)-gallocatechin- (4α-8)-(-)-epigallocatechin-(4β-8)-(-)-epigallocatechin-(4β-8)- (-) -epigallocatechin-(4β-8)-(+)-catechin - CS-1 and 3-O-galloyl-7-O-(β-D-Glcp → 6O-β-D-Glcp)-(-)-epigallocatechin-(4β-8)-[3-O-galloyl-(-)- epigallocatechin]-(4β-8)-[3-O-galloyl-(-)-epigallocatechin]-(4β-8)-[3- O-galloyl-5-O-(6-O-galloyl-O-β-D-Glcp)]-(-)-epicatechin - CS-2.
