(-)-Epigallocatechin gallate

Names

[ CAS No. ]:
989-51-5

[ Name ]:
(-)-Epigallocatechin gallate

[Synonym ]:
TEA CATECHIN
(-)-epigallocatechin 3-gallate
(2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate
Epigallocatechin 3-gallate
EGCG
MFCD00075940
Benzoic acid, 3,4,5-trihydroxy-, (2R,3R)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester
(-)-Epigallocatechin-3-o-gallate
Epigallocatechin gallate
E-5187
(-)-Epigallocatechin 3-O-gallate
3,4,5-Trihydroxybenzoic acid (2R-cis)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester
(-)-EGCG
Teavigo
ECGC
EINECS 479-560-7
Teavigo TG
(-)-Epigallocatechin gallate
EGCG-d6
Epigallocatechin-3-gallate
(−)-cis-3,3',4',5,5',7-Hexahydroxy-flavane-3-gallate

Biological Activity

[Description]:

(-)-Epigallocatechin Gallate is an antioxidant polyphenol flavonoid form green tea, and inhibits the activation of EGFR, HER2 and HER3, with antitumor activity.

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> JAK/STAT Signaling >> EGFR

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> EGFR

Research Areas >> Cancer

Natural Products >> Flavonoids

[Target]

EGFR

HER2

HER3

[In Vitro]

(-)-Epigallocatechin Gallate (EGCG) inhibits activation EGFR, HER2 and HER3 in the SW837 human colon cancer cell line. (-)-Epigallocatechin Gallate (10 μM) also inhibits cell growth, suppresses activation of EGFR, HER2, and HER3, and causes decrease in the levels of COX-2 and Bcl-xL proteins, and apoptosis after treatment for 96 h[1]. (-)-Epigallocatechin Gallate (0-35 μg/mL) inhibits the proliferation of colorectal cancer cells. (-)-Epigallocatechin Gallate (35 μg/mL) induces apoptosis of colorectal cancer cells[2]. (-)-Epigallocatechin Gallate (EGCG; 50, 75 and 100 μM) dose-dependently inhibits the growth of HepG2 cells, and induces apoptosis in HepG2 cells[3].

[In Vivo]

(-)-Epigallocatechin Gallate (5, 10, and 20 mg/kg, p.o.) inhibits the growth of orthotopic colorectal cancer cells in mice[2].

[Cell Assay]

LoVo, SW480, HCT-8, and HT-29 cells are seeded in 96-well plates at a concentration of 5×103 cells; each cell line is totally seeded in the 12 wells. Complete medium is added to the wells, up to 200 μL; the medium contains 0 μg/mL, 10 μg/mL, 20 μg/mL, and 35 μg/mL of (-)-Epigallocatechin Gallate. The inhibition rate=[1 - (absorbance of (-)-Epigallocatechin Gallate group - absorbance of control group)/(absorbance of control group - absorbance of blank control group)] × 100[2].

[Animal admin]

Mice[2] At 2 weeks postsurgery, 39 out of the 40 nude mice presented with tumors. Based on the volume of the tumors, the 39 mice with tumors are divided into four groups: a control group (n=9); a group that receives 5 mg/kg of (-)-Epigallocatechin Gallate (n=10); a group that receives 10 mg/kg of (-)-Epigallocatechin Gallate (n=10); and a group that receives 20 mg/kg of (-)-Epigallocatechin Gallate (n=10). In the therapeutic groups, (-)-Epigallocatechin Gallate is administrated intragastrically, and in the control group, 100 uL of physiological saline is administrated intragastrically, once daily for 14 days. After the treatment of the mice with (-)-Epigallocatechin Gallate for 4 weeks, the growth and metastasis of the primary tumors are continuously monitored using a fluorescent imaging system. After 4 weeks, the primary tumors are weighed and immediately put into liquid nitrogen (−196°C) and 2 to 3 hours later, these specimens are stored at −80°C. In addition, the other parts of the primary tumor and metastases are fixed in 4% formaldehyde[2].

[References]

[1]. De Amicis F, et al. Epigallocatechin gallate inhibits growth and Epithelial-to-Mesenchymal Transition in human thyroid carcinoma cell lines. J Cell Physiol. 2013 Apr 1.

[2]. Jin H, et al. Epigallocatechin gallate inhibits the proliferation of colorectal cancer cells by regulating Notch signaling. Onco Targets Ther. 2013;6:145-53.

[3]. Wing Pui Tsang, et al. Epigallocatechin gallate up-regulation of miR-16 and induction of apoptosis in human cancer cells. The Journal of Nutritional Biochemistry. 2010, 21(2): 140-146.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Boiling Point ]:
909.1±65.0 °C at 760 mmHg

[ Melting Point ]:
222-224°C

[ Molecular Formula ]:
C₂₂H₁₈O₁₁

[ Molecular Weight ]:
458.372

[ Flash Point ]:
320.0±27.8 °C

[ Exact Mass ]:
458.084900

[ PSA ]:
197.37000

[ LogP ]:
2.08

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.857

[ Storage condition ]:
2-8°C

[ Stability ]:
Stable, but may be light sensitive. Incompatible with strong oxidizing agents.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KB5200000

CHEMICAL NAME :: Epigallocatechol, 3-gallate, (-)-

CAS REGISTRY NUMBER :: 989-51-5

LAST UPDATED :: 198809

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C22-H18-O11

MOLECULAR WEIGHT :: 458.40

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2170 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 21,4601,1987

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
F+

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
KB5200000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Mechanism of Dose-Dependent Regulation of UBE1L by Polyphenols in Human Bronchial Epithelial Cells.

J. Cell. Biochem. 116 , 1553-62, (2015)

Ubiquitin activating enzyme E1-like (UBE1L) is the activating enzyme for ISG15ylation (ISG15, interferon stimulated gene 15). UBE1L is thought to be a candidate tumor suppressor gene and has positive ...

Green tea polyphenol (-)-epigallocatechin-3-gallate triggered hepatotoxicity in mice: responses of major antioxidant enzymes and the Nrf2 rescue pathway.

Toxicol. Appl. Pharmacol. 283(1) , 65-74, (2015)

(-)-Epigallocatechin-3-gallate (EGCG), a constituent of green tea, has been suggested to have numerous health-promoting effects. On the other hand, high-dose EGCG is able to evoke hepatotoxicity. In t...

Epigenetic induction of tissue inhibitor of matrix metalloproteinase-3 by green tea polyphenols in breast cancer cells.

Mol. Carcinog. 54(6) , 485-99, (2015)

Aberrant epigenetic silencing of the tissue inhibitor of matrix metalloproteinase-3 (TIMP-3) gene that negatively regulates matrix metalloproteinases (MMPs) activity has been implicated in the pathoge...

Related Compounds

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