(-)-Catechin gallate(CG)

Names

[ Name ]:
(-)-Catechin gallate(CG)

[Synonym ]:
(−)-Catechin gallate
(2S,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate
MFCD00214258
(2S,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxychroman-3-yl 3,4,5-trihydroxybenzoate
[(2S,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
Benzoic acid, 3,4,5-trihydroxy-, (2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl ester

Biological Activity

[Description]:

(-)-Catechin gallate is a minor constituent in green tea catechins. (-)-Catechin gallate inhibits the activity of COX-1 and COX-2 enzymes.

[Related Catalog]:

Research Areas >> Cancer

Natural Products >> Flavonoids

[Target]

COX-1

COX-2

[In Vitro]

(-)-Catechin gallate (CG) directly interacts with DNA oligomers and inhibits the activity of COX-1 and COX-2 enzymes, the gene expression of matrix metalloproteinase-9 in macrophage-differentiated HL-60 myeloid leukemia cells, the adipocyte uptake of glucose by the transporter, GLUT4, and the activities of various proteasomes, i.e., the multicatalytic proteases responsible for the degradation of most cellular proteins. The relative cytotoxicities of a 3-day exposure to (-)-Catechin gallate are determined for cancerous CAL27 and HSG cells, immortalized epithelioid S-G cells, and normal HGF-1 gingival fibroblasts. The concentration at which toxicity (P≤0.01) initially occur is 25 μM (-)-Catechin gallate for S-G cells, 50 μM (-)-Catechin gallate for CAL27 cells, 62.5 μM (-)-Catechin gallate for HSG cells and 75 μM (-)-Catechin gallate for HGF-1 fibroblasts. The calculated neutral red (NR50) values for a 3-day exposure to (-)-Catechin gallate are 58 μM for S-G cells, 62 μM for CAL27 cells, 90 μM for HSG cells and 132 μM for HGF-1 fibroblasts[1].

[Cell Assay]

Human tongue squamous carcinoma (CAL27) cells and human salivary gland carcinoma (HSG) cells are used. Individual wells of a 96-well microtiter tissue culture plate are inoculated with 0.2 mL of the growth medium containing 2×104 cells/well for a 1-day exposure, 1.5×104 cells/ well for a 2-day exposure and 1×104 cells/well for a 3-day exposure to the test agents. After 1 day of incubation, the growth medium is removed and replaced with exposure medium, with or without varied concentrations of the test agents. In some studies the cells are coexposed to (-)-Catechin gallate (100, 200, 300, 400, and 500 μM) and 100 Units/mL catalase. After 1-3 days of exposure to the test agents, viability is assessed with the neutral red (NR) assay, which is based on the uptake and accumulation of the supravital dye, neutral red (NR)[1].

[References]

[1]. Babich H, et al. In vitro cytotoxicity of (-)-catechin gallate, a minor polyphenol in green tea. Toxicol Lett. 2007 Jul 10;171(3):171-80.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
861.7±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₂H₁₈O₁₀

[ Molecular Weight ]:
442.372

[ Flash Point ]:
305.0±27.8 °C

[ Exact Mass ]:
442.089996

[ PSA ]:
177.14000

[ LogP ]:
2.67

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

[ Index of Refraction ]:
1.825

[ Storage condition ]:
2~8℃

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Development and validation of UHPLC-MS/MS method for determination of eight naturally occurring catechin derivatives in various tea samples and the role of matrix effects.

J. Pharm. Biomed. Anal. 114 , 62-70, (2015)

A complete analytical procedure combining optimized tea infusion preparation and validated UHPLC-MS/MS method was developed for routine quantification of eight naturally occurring catechin derivatives...

Catechin gallates are NADP+-competitive inhibitors of glucose-6-phosphate dehydrogenase and other enzymes that employ NADP+ as a coenzyme.

Bioorg. Med. Chem. 16 , 3580-6, (2008)

Recent studies have shown that glucose-6-phosphate dehydrogenase (G6PD) is an effectual therapeutic target for metabolic disorders, including obesity and diabetes. In this study, we used in silico and...

Flavonoids as opioid receptor ligands: identification and preliminary structure-activity relationships.

J. Nat. Prod. 70 , 1278-82, (2007)

Flavonoids have been recognized as the active ingredients of many medicinal plant extracts due to interactions with proteins via phenolic groups and low toxicity. Here, we report the investigation of ...