Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H18O11 |
Molecular Weight | 458.3717 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C4=CC(O)=C(O)C(O)=C4)C(O)=C1
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
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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Pharmacokinetics of the green tea derivative, EGCG, by the topical route of administration in mouse and human skin. | 1999 |
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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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Anti-herpes simplex virus type-1 flavonoids and a new flavanone from the root of Limonium sinense. | 2000 May |
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Epigallocatechin gallate protects U937 cells against nitric oxide-induced cell cycle arrest and apoptosis. | 2001 |
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Inactivation of parvovirus B19 in coagulation factor concentrates by UVC radiation: assessment by an in vitro infectivity assay using CFU-E derived from peripheral blood CD34+ cells. | 2001 Apr |
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Prolyl endopeptidase inhibitors from green tea. | 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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Anticarcinogenic antioxidants as inhibitors against intracellular oxidative stress. | 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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The green tea polyphenol (-)-epigallocatechin gallate attenuates beta-amyloid-induced neurotoxicity in cultured hippocampal neurons. | 2001 Dec 21 |
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Synthesis of (-)-[4-3H]epigallocatechin gallate and its metabolic fate in rats after intravenous administration. | 2001 Feb |
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Green tea polyphenols as potent enhancers of glucocorticoid-induced mouse mammary tumor virus gene expression. | 2001 Feb 16 |
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Degradation of green tea catechins in tea drinks. | 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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Stereospecificity in membrane effects of catechins. | 2001 Mar 14 |
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Phase I trial of oral green tea extract in adult patients with solid tumors. | 2001 Mar 15 |
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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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Combination effect of lignin F and natural products. | 2001 Mar-Apr |
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Green tea polyphenol (-)-epigallocatechin-3-gallate treatment to mouse skin prevents UVB-induced infiltration of leukocytes, depletion of antigen-presenting cells, and oxidative stress. | 2001 May |
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Inhibitory effect of epigallocatechin gallate on adhesion of murine melanoma cells to laminin. | 2001 Nov 8 |
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Inhibition of UVB-induced oxidative stress-mediated phosphorylation of mitogen-activated protein kinase signaling pathways in cultured human epidermal keratinocytes by green tea polyphenol (-)-epigallocatechin-3-gallate. | 2001 Oct 15 |
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Green tea constituent (--)-epigallocatechin-3-gallate inhibits topoisomerase I activity in human colon carcinoma cells. | 2001 Oct 19 |
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Simplified catechin-gallate inhibitors of HIV-1 reverse transcriptase. | 2001 Oct 22 |
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A novel method of measuring hydroxyl radical-scavenging activity of antioxidants using gamma-irradiation. | 2001 Sep |
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Epigallocatechin gallate (EGCG) inhibits the sulfation of 1-naphthol in a human colon carcinoma cell line, Caco-2. | 2001 Sep |
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Green tea polyphenol (-)-epigallocatechin-3-gallate prevents N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced dopaminergic neurodegeneration. | 2001 Sep |
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Epigallocatechin gallate synergy with ampicillin/sulbactam against 28 clinical isolates of methicillin-resistant Staphylococcus aureus. | 2001 Sep |
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The green tea polyphenol (-)-epigallocatechin-3-gallate blocks nuclear factor-kappa B activation by inhibiting I kappa B kinase activity in the intestinal epithelial cell line IEC-6. | 2001 Sep |
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Effects of (-)-epigallocatechin-3-gallate, the main component of green tea, on the cloned rat brain Kv1.5 potassium channels. | 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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Inhibitory effects of (-)-epigallocatechin gallate on the life cycle of human immunodeficiency virus type 1 (HIV-1). | 2002 Jan |
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In vitro therapeutic effect of epigallocatechin gallate on nicotine-induced impairment of resistance to Legionella pneumophila infection of established MH-S alveolar macrophages. | 2002 Jan 15 |
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Synergistic effects of (-)-epigallocatechin gallate with sulindac against colon carcinogenesis of rats treated with azoxymethane. | 2002 Mar 8 |
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.
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NCI_THESAURUS |
C68454
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DSLD |
2960 (Number of products:2)
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1193 (Number of products:210)
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1236700
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65064
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C1088
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4806
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DB12116
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EPIGALLOCATECHIN GALLATE
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DTXSID1029889
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SUB33667
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m4843
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C045651
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100000127611
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BQM438CTEL
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ACTIVE MOIETY