(-)-Epigallocatechin gallate

(-)-Epigallocatechin gallate

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It is produced by the strain of Nocardia sp. C-15003(N-1). It has the function of anti-tumor, anti-plant pathogenic fungi, skin fungi and protozoa, and has no antibacterial activity.

(-)-Epigallocatechin gallate

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BBF-03974 50 g $319 In stock
BBF-03974 100 g $439 In stock
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Catalog Number BBF-03974
CAS 989-51-5
Description EGCG is an antioxidant extracted from green tea, reduces Aβ42-induced cell death in three different cell types and inhibits β-secretase (IC50 = 1.6 μM). (-)-Epigallocatechin gallate is a natural compound found in the woods of Acacia catechu (L.F.) Willd. It can be used in cosmetic material.
Related CAS970-74-1
Molecular Formula C22H18O11
Molecular Weight 458.37
Synonyms EGCG cpd; epigallo-catechin gallate; epigallocatechin gallate; epigallocatechin-3-gallate; epigallocatechin-3-O-gallate; EGCG
IUPAC Name [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
Canonical SMILES C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O
InChI 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
Boiling Point 909.1°C at 760 mmHg
Melting Point 213-216°C
Purity >98%
Density 1.9 g/cm3
Solubility Soluble in water, ethanol
Appearance White Solid
Storage Store at -20°C
1.Antiallodynic effect of intrathecal epigallocatechin-3-gallate due to suppression of reactive oxygen species.
An SS;Kim YO;Park CH;Lin H;Yoon MH Korean J Anesthesiol. 2014 Aug;67(2):123-8. doi: 10.4097/kjae.2014.67.2.123. Epub 2014 Aug 26.
BACKGROUND: ;Green tea modulates neuropathic pain. Reactive oxygen species (ROS) are suggested as a key molecule in the underlying mechanism of neuropathic pain in the spinal cord. We examined the effect of epigallocatechin-3-gallate (EGCG), the major catechin in green tea, in neuropathic pain and clarified the involvement of ROS on the activity of EGCG.;METHODS: ;Neuropathic pain was induced in male Sprague-Dawley rats by spinal nerve ligation (SNL). A polyethylene tube was intrathecally located. Nociceptive degree was estimated by a von Frey filament and expressed as a paw withdrawal threshold (PWT). To determine the role of ROS on the effect of EGCG, a free radical donor (tert-BuOOH) was pretreated before administration of EGCG. ROS activity was assayed by xanthine oxidase (XO) and malondialdehyde (MDA).;RESULTS: ;SNL decreased the PWT compared to sham rats. The decrease remained during the entire observation period. Intrathecal EGCG increased the PWT at the SNL site. Intrathecal tert-BuOOH significantly decreased the effect of EGCG. The levels of both XO and MDA in the spinal cord were increased in SNL rats compared to sham. Intrathecal EGCG decreased the level of XO and MDA.;CONCLUSIONS: ;EGCG may reduce neuropathic pain by SNL due to the suppression of ROS in the spinal cord.
2.Validation of a high performance liquid chromatography method for the stabilization of epigallocatechin gallate.
Fangueiro JF;Parra A;Silva AM;Egea MA;Souto EB;Garcia ML;Calpena AC Int J Pharm. 2014 Nov 20;475(1-2):181-90. doi: 10.1016/j.ijpharm.2014.08.053. Epub 2014 Aug 28.
Epigallocatechin gallate (EGCG) is a green tea catechin with potential health benefits, such as anti-oxidant, anti-carcinogenic and anti-inflammatory effects. In general, EGCG is highly susceptible to degradation, therefore presenting stability problems. The present paper was focused on the study of EGCG stability in HEPES (N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid) medium regarding the pH dependency, storage temperature and in the presence of ascorbic acid a reducing agent. The evaluation of EGCG in HEPES buffer has demonstrated that this molecule is not able of maintaining its physicochemical properties and potential beneficial effects, since it is partially or completely degraded, depending on the EGCG concentration. The storage temperature of EGCG most suitable to maintain its structure was shown to be the lower values (4 or -20 °C). The pH 3.5 was able to provide greater stability than pH 7.4. However, the presence of a reducing agent (i.e., ascorbic acid) was shown to provide greater protection against degradation of EGCG. A validation method based on RP-HPLC with UV-vis detection was carried out for two media: water and a biocompatible physiological medium composed of Transcutol®P, ethanol and ascorbic acid.
3.Epigallocatechin gallate protects BEAS-2B cells from lipopolysaccharide-induced apoptosis through upregulation of gastrin-releasing peptide.
Divya P;Puthusseri B;Manual DJK;Savanur MA Mol Cell Biochem. 2017 Oct;434(1-2):105-111. doi: 10.1007/s11010-017-3040-y. Epub 2017 Apr 21.
Gastrin-releasing peptide (GRP) plays a major role in the development and maintenance of lung epithelial cells by promoting cell division, whereas its suppression causes growth arrest and apoptosis. The present study shows that human bronchial epithelial BEAS-2B cells challenged with lipopolysaccharide (LPS), an endotoxin from gram-negative bacteria, downregulated GRP expression and induced apoptosis via upregulation of p53 and active caspase-3, signifying the importance of GRP in lung epithelial cell survival. However, in the presence of epigallocatechin-3-gallate (EGCG), a polyphenol in green tea, BEAS-2B cells resisted LPS-induced apoptosis and restored the expression of GRP and its downstream effectors such as epidermal growth factor receptor and NF-κB, as analysed by immunoblotting and qPCR. Based on our findings, we objectify that cytoprotective functions of EGCG, via upregulation of GRP in cells challenged with LPS, are novel and can be further explored in a therapeutic point of view for diseases such as septic shock.

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