Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H18O11 |
Molecular Weight | 458.3726 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
c1c(cc(c(c1O)O)O)[C@]2([H])[C@@]([H])(Cc3c(cc(cc3O2)O)O)OC(=O)c4cc(c(c(c4)O)O)O
InChI
InChIKey=WMBWREPUVVBILR-WIYYLYMNSA-N
InChI=1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1
Molecular Formula | C22H18O11 |
Molecular Weight | 458.3726 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Epigallocatechin-3-gallate (EGCG), the major polyphenol from green tea, has the potential to impact a variety of human diseases. EGCG functions as a powerful antioxidant, preventing oxidative damage in healthy cells, but also as an antiangiogenic and antitumor agent and as a modulator of tumor cell response to chemotherapy. It was shown, that EGCG can inhibit 5-cytosine DNA methyltransferase (DNMT) activity and reactivate methylation-silenced genes in cancer cells and another of the probable mechanisms by EGCG exercise their anti-tumor property is through the suppression of the NFκB signaling pathway. EGCG has emerged as a potential neuroprotective agent for the treatment of neurological disorders associated with harmful effects of reactive oxygen species. The neuroprotective mechanism of action is probably based on several factors, including EGCG's modulation of several signal transduction pathways, its influence on the expression of genes regulating cell survival or programmed cell death, as well as its modulation of mitochondrial function. A phase II/III trial of oral Sunphenon epigallocatechin-3-gallate in patients with progressive multiple sclerosis has been completed. In addition, EGCG was in phase III clinical trials for the treatment of multiple system atrophy and for patients with Duchenne Muscular Dystrophy ((DMD). DMD is the most frequent neuromuscular condition to occur in childhood and youth.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28956003
Curator's Comment:: A low concentration of epigallocatechin gallate that was suggested from BBB permeability may prevent cognitive dysfunction by increasing brain plasticity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P26358 Gene ID: 1786.0 Gene Symbol: DNMT1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14633667 |
6.89 µM [Ki] | ||
Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21827739 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Mechanisms of cancer prevention by tea polyphenols based on inhibition of TNF-alpha expression. | 2000 |
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A new concept of tumor promotion by tumor necrosis factor-alpha, and cancer preventive agents (-)-epigallocatechin gallate and green tea--a review. | 2000 |
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Correlation of chemopreventive efficacy data from the human epidermal cell assay with in vivo data. | 2000 Jan-Feb |
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Developing a dynamic pharmacophore model for HIV-1 integrase. | 2000 Jun 1 |
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Preventive effect of antioxidant on ultraviolet-induced skin cancer in mice. | 2000 Mar |
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Anti-herpes simplex virus type-1 flavonoids and a new flavanone from the root of Limonium sinense. | 2000 May |
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Differential responses of skin cancer-chemopreventive agents silibinin, quercetin, and epigallocatechin 3-gallate on mitogenic signaling and cell cycle regulators in human epidermoid carcinoma A431 cells. | 2001 |
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Ester bond-containing tea polyphenols potently inhibit proteasome activity in vitro and in vivo. | 2001 Apr 20 |
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The molecular interaction of human salivary histatins with polyphenolic compounds. | 2001 Aug |
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Tea catechin, (-)-epigallocatechin gallate, causes membrane depolarizations of myenteric neurons in the guinea-pig small intestine. | 2001 Aug 24 |
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Apoptosis induction by epigallocatechin gallate involves its binding to Fas. | 2001 Aug 3 |
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Plasma concentrations of individual tea catechins after a single oral dose in humans. | 2001 Dec |
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Rapid conversion of tea catechins to monomethylated products by rat liver cytosolic catechol-O-methyltransferase. | 2001 Dec |
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The medicinal action of androgens and green tea epigallocatechin gallate. | 2001 Dec |
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Effect of polyphenols on calcium content and alkaline phosphatase activity in rat femoral tissues in vitro. | 2001 Dec |
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Effects of epigallocatechin-3-gallate on growth, epidermal growth factor receptor signaling pathways, gene expression, and chemosensitivity in human head and neck squamous cell carcinoma cell lines. | 2001 Dec |
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The green tea polyphenol (-)-epigallocatechin gallate attenuates beta-amyloid-induced neurotoxicity in cultured hippocampal neurons. | 2001 Dec 21 |
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Evaluation of antioxidant activity of epigallocatechin gallate in biphasic model systems in vitro. | 2001 Feb |
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Green tea polyphenol (-)-epigallocatechin-3-gallate treatment of human skin inhibits ultraviolet radiation-induced oxidative stress. | 2001 Feb |
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Tumor gelatinases and invasion inhibited by the green tea flavanol epigallocatechin-3-gallate. | 2001 Feb 15 |
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Phase I pharmacokinetic study of tea polyphenols following single-dose administration of epigallocatechin gallate and polyphenon E. | 2001 Jan |
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Protective effects of (-)-epigallocatechin-3-gallate on UVA- and UVB-induced skin damage. | 2001 Jan-Feb |
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Oxygen radical absorbance capacity of the phenolic compounds in plant extracts fractionated by high-performance liquid chromatography. | 2001 Jun 15 |
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A simple isolation method for the major catechins in green tea using high-speed countercurrent chromatography. | 2001 Mar |
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Antimutagenic activity of green tea and black tea extracts studied in a dynamic in vitro gastrointestinal model. | 2001 Mar 1 |
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Stereospecificity in membrane effects of catechins. | 2001 Mar 14 |
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Enantioselective synthesis of epigallocatechin-3-gallate (EGCG), the active polyphenol component from green tea. | 2001 Mar 8 |
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Anti-interferon gamma action of epigallocatechin-3-gallate mediated by specific inhibition of STAT1 activation. | 2001 May |
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Mechanisms of inhibition of the Ras-MAP kinase signaling pathway in 30.7b Ras 12 cells by tea polyphenols (-)-epigallocatechin-3-gallate and theaflavin-3,3'-digallate. | 2001 Sep |
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Cancer prevention with green tea and monitoring by a new biomarker, hnRNP B1. | 2001 Sep 1 |
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Molecular mechanisms underlying chemopreventive activities of anti-inflammatory phytochemicals: down-regulation of COX-2 and iNOS through suppression of NF-kappa B activation. | 2001 Sep 1 |
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(-)Epigallocatechin-3-gallate inhibits leukocyte elastase: potential of the phyto-factor in hindering inflammation, emphysema, and invasion. | 2002 Jan |
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Angioprevention': angiogenesis is a common and key target for cancer chemopreventive agents. | 2002 Jan |
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Potentiometric and (1)H NMR studies of complexation of Al(3+) with (-)-epigallocatechin gallate, a major active constituent of green tea. | 2002 Jan 1 |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT00799890
Sunphenon EGCG (Epigallo Catechin Gallate) 200-800mg (1-4 capsules)
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29042941
Epigallocatechin gallate (EGCG) could inhibit the viability and invasion, and induce the apoptosis, of bladder cancer T24 cells. The apoptosis of bladder cancer cells was notably increased by 20 µm EGCG. In addition, 20 µm EGCG inhibited bladder cancer cell viability. However, 10 µm EGCG did not exhibit any significant inhibitory effect on T24 cell viability. The effect of EGCG on the invasive ability of the bladder cancer cells was then investigated, which demonstrated that 10 µm and 20 µm of EGCG significantly inhibited invasion compared with the control group.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 21:27:39 UTC 2021
by
admin
on
Fri Jun 25 21:27:39 UTC 2021
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Record UNII |
BQM438CTEL
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C68454
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DSLD |
2960 (Number of products:2)
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DSLD |
1193 (Number of products:210)
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1236700
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65064
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C1088
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DB12116
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EPIGALLOCATECHIN GALLATE
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989-51-5
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BQM438CTEL
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SUB33667
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M4843
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C045651
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989-51-5
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24246
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PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT | |||
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TRANSPORTER -> INHIBITOR |
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ACTIVE MOIETY |