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(-)-Epigallocatechin gallate

[EGCG, (2R,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 3-(3,4,5-trihydroxybenzoate)]



ALX-270-263-M010	10 mg	20.00 USD

ALX-270-263-M050	50 mg	60.00 USD

Replaces Prod. #: BML-FR109

Antitumor reagent. Antioxidant. Protects cells from lipid peroxidation and DNA damage induced by reactive free radicals. Inhibits inducible nitric oxide synthase (iNOS; NOS II). Chemopreventive anticancer agent. Induces apoptosis in human cancer cell lines. Inhibits MAP kinase mediated signalling pathways. Inhibits angiogenesis. Inhibits telomerase and DNA methyltransferase. Anti-inflammatory agent.

Product Specification

Formula:	C₂₂H₁₈O₁₁

MW:	458.4

Purity:	≥98% (HPLC)

Appearance:	Off-white to yellow powder.

CAS:	989-51-5

MI:	14: 3526

Source/Host:	Isolated from green tea.

Solubility:	Soluble in 100% ethanol, dimethyl formamide or DMSO; slightly soluble in water.

Shipping:	AMBIENT

Long Term Storage:	+4°C

Use/Stability:	Stock solutions in DMSO are stable for up to 3 months when stored at -20°C.

Handling:	After reconstitution, prepare aliquots and store at -20°C. Keep under inert gas. Protect from light.

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Product Literature References

Inhibitory effect of topical application of a green tea polyphenol fraction on tumor initiation and promotion in mouse skin: M.T. Huang, et al.; Carcinogenesis 13, 947 (1992), Abstract;

S. Miura et al.; Biol. Pharm. Bull. 18, 1 (1995),

Growth inhibition and regression of human prostate and breast tumors in athymic mice by tea epigallocatechin gallate: S. Liao, et al.; Cancer Lett. 96, 239 (1995), Abstract;

Inhibition of 12-O-tetradecanoylphorbol-13-acetate and other skin tumor-promoter-caused induction of epidermal interleukin-1 alpha mRNA and protein expression in SENCAR mice by green tea polyphenols: S.K. Katiyar, et al.; J. Invest. Dermatol. 105, 394 (1995), Abstract;

Inhibition of N-methyl-N'-nitro-N-nitrosoguanidine-induced carcinogenesis by (-)-epigallocatechin gallate in the rat glandular stomach: T. Yamane, et al.; Cancer Res. 55, 2081 (1995), Abstract;

(-)-Epigallocatechin gallate, a polyphenolic tea antioxidant, inhibits peroxynitrite-mediated formation of 8-oxodeoxyguanosine and 3-nitrotyrosine: E.S. Fiala, et al.; Experientia 52, 922 (1996), Abstract;

(-)-Epigallocatechin-3-gallate blocks the induction of nitric oxide synthase by down-regulating lipopolysaccharide-induced activity of transcription factor nuclear factor-kappaB: Y.L. Lin & J.K. Lin; Mol. Pharmacol. 52, 465 (1997), Abstract;

Green tea constituent epigallocatechin-3-gallate and induction of apoptosis and cell cycle arrest in human carcinoma cells: N. Ahmad, et al.; J. Natl. Cancer Inst. 89, 1881 (1997), Abstract;

Inhibition of inducible nitric oxide synthase gene expression and enzyme activity by epigallocatechin gallate, a natural product from green tea: M.M. Chan, et al.; Biochem. Pharmacol. 54, 1281 (1997), Abstract;

Epigallocatechin suppression of proliferation of vascular smooth muscle cells: correlation with c-jun and JNK: L.H. Lu, et al.; Br. J. Pharmacol. 124, 1227 (1998), Abstract;

Green tea epigallocatechin gallate shows a pronounced growth inhibitory effect on cancerous cells but not on their normal counterparts: Z.P. Chen et al.; Cancer Lett. 129, 173 (1998), Abstract;

Induction of apoptosis in prostate cancer cell lines by the green tea component, (-)-epigallocatechin-3-gallate: A.G. Paschka et al.; Cancer. Lett. 130, 1 (1998), Abstract;

Telomerase inhibition, telomere shortening, and senescence of cancer cells by tea catechins: I. Naasani, et al.; BBRC 249, 391 (1998), Abstract;

Antimutagenic and anticarcinogenic activity of tea polyphenols: Y. Kuroda & Y. Hara; Mutat. Res. 436, 69 (1999), Abstract;

Antioxidant chemistry of green tea catechins. Identification of products of the reaction of (-)-epigallocatechin gallate with peroxyl radicals: S. Valcic, et al.; Chem. Res. Toxicol. 12, 382 (1999), Abstract;

ESR study on the structure-antioxidant activity relationship of tea catechins and their epimers: Q. Guo, et al.; Biochim. Biophys. Acta 1427, 13 (1999), Abstract;

Inhibitory effect of green and black tea on tumor growth: A.H. Conney, et al.; Proc. Soc. Exp. Biol. Med. 220, 229 (1999), Abstract;

Pharmacokinetics of the green tea derivative, EGCG, by the topical route of administration in mouse and human skin: K. Dvorakova, et al.; Cancer Chemother. Pharmacol. 43, 331 (1999), Abstract;

Polyphenolic antioxidant (-)-epigallocatechin-3-gallate from green tea reduces UVB-induced inflammatory responses and infiltration of leukocytes in human skin: S.K. Katiyar, et al.; Photochem. Photobiol. 69, 148 (1999), Abstract;

Matrix metalloproteinase inhibition by green tea catechins: M. Demeule et al.; Biochim. Biophys. Acta 1478, 51 (2000), Abstract;

Green tea epigallocatechin gallate: a natural inhibitor of fatty-acid synthase: X. Wang & W. Tian; BBRC 288, 1200 (2001), Abstract;

Tumor gelatinases and invasion inhibited by the green tea flavanol epigallocatechin-3-gallate: S. Garbisa et al.; Cancer 91, 822 (2001), Abstract;

(-)Epigallocatechin-3-gallate inhibits leukocyte elastase: potential of the phyto-factor in hindering inflammation, emphysema, and invasion: L. Sartor et al.; J. Leukoc. Biol. 71, 73 (2002), Abstract;

Epigallocatechin gallate, a constituent of green tea, represses hepatic glucose production: M.E. Waltner-Law, et al.; J. Biol. Chem. 277, 34933 (2002), Abstract; Full Text

Fenton reaction is primarily involved in a mechanism of (-)-epigallocatechin-3-gallate to induce osteoclastic cell death: H. Nakagawa et al.; Biochem. Biophys. Res. Commum 292, 94 (2002), Abstract;

Inhibitory effects of green tea catechins on the activity of human matrix metalloproteinase 7 (matrilysin): H. Oneda et al.; J. Biochem. 133, 571 (2003), Abstract;

Selective inhibition of ADAMTS-1, -4 and -5 by catechin gallate esters: M.N. Vankemmelbeke, et al.; Eur. J. Biochem. 270, 2394 (2003), Abstract;

The specificities of protein kinase inhibitors: an update:: J. Bain, et al.; Biochem. J. 371, 199 (2003), Abstract; Full Text

A constituent of green tea, epigallocatechin-3-gallate, activates endothelial nitric oxide synthase by a phosphatidylinositol-3-OH-kinase-, cAMP-dependent protein kinase-, and Akt-dependent pathway and leads to endothelial-dependent vasorelaxation: M. Lorenz, et al.; J. Biol. Chem. 279, 6190 (2004), Abstract; Full Text

Epigallocatechin-3-gallate inhibits epidermal growth factor receptor signaling pathway. Evidence for direct inhibition of ERK1/2 and AKT kinases: J.F. Sah, et al.; J. Biol. Chem. 279, 12755 (2004), Abstract;

Epigallocatechin-3-gallate, constituent of green tea, suppresses the LPS-induced phenotypic and functional maturation of murine dendritic cells through inhibition of mitogen-activated protein kinases and NF-kappaB: S.C. Ahn, et al.; BBRC 313, 148 (2004), Abstract;

Green tea polyphenols prevent toxin-induced hepatotoxicity in mice by down-regulating inducible nitric oxide-derived prooxidants: J.H. Chen, et al.; Am. J. Clin. Nutr. 80, 742 (2004), Abstract; Full Text

Inhibition of c-Jun NH2-terminal kinase activity improves ischemia/reperfusion injury in rat lungs: M. Ishii, et al.; J. Immunol. 172, 2569 (2004), Abstract;

Neuroprotective effects of (-)-epigallocatechin gallate following hypoxia-ischemia-induced brain damage: novel mechanisms of action: B.A. Sutherland, et al.; FASEB J. 19, 258 (2005), Abstract; Full Text

Tea flavanols inhibit angiotensin-converting enzyme activity and increase nitric oxide production in human endothelial cells: I.A. Persson, et al.; J. Pharm. Pharmacol. 58, 1139 (2006), Abstract;

General Literature References

Anticarcinogenic effects of (-)-epigallocatechin gallate H. Fujiki, et al. Prev. Med. 21 503 (1992) (Review) Abstract

Absorption, metabolism and antioxidative effects of tea catechin in humans T. Miyazawa Biofactors 13 55 (2000) (Review) Abstract

Inhibition of tumour invasion and angiogenesis by epigallocatechin gallate (EGCG), a major component of green tea Y.D. Jung and L.M. Ellis Int. J. Exp. Pathol. 82 309 (2001) (Review) Abstract

Anti-invasive effects of green tea polyphenol epigallocatechin-3-gallate (EGCG), a natural inhibitor of metallo and serine proteases R. Benelli, et al. Biol. Chem. 383 101 (2002) (Review) Abstract