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G6657 Sigma

(−)-Gallocatechin

≥98% (HPLC)

Synonym: (2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol

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Description

Other Notes

Polyphenolic compound found in green tea. An epimer of (−)-epigallocatechin.

Packaging

1, 5 mg in glass bottle

Biochem/physiol Actions

Possesses free radical scavenging ability. Inhibits the growth and adherence of P. gingivalis onto the buccal epithelial cells.

Protocols & Applications

Ginkgo (Ginkgo biloba) Plant Profile: bioactives, mechanism of action, references

Price and Availability

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Laboratory GlovesThis substance has been tested against several types of hand protection for CE compliance. Click below to find the recommended gloves for handling this product.




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(−)-Catechin gallate

≥98% (HPLC), from green tea

(−)-Epigallocatechin

analytical standard

(−)-Epigallocatechin

≥95% (HPLC), from green tea

(−)-Gallocatechin

analytical standard

(−)-Gallocatechin gallate

from green tea, ≥98% (HPLC)

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xi
Risk Statements (Europe) 
Safety Statements (Europe) 
26-36
WGK Germany 
3

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Dietary Antioxidants

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.1 During the oxi...
BioFiles 2007, 2.2, 2.
Keywords: Adhesion, Anti-inflammatory agents, Applications, Cancer, Cardiovascular, Catalysis, Diabetes, Diseases, Gene expression, Metabolism, Neurodegenerative Diseases, Peroxidations, Phosphorylations, Prebiotics, Probiotics, Reductions, Transcription, Transduction, Vitamins

Peer-Reviewed Papers

References

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Inhibitory effects of green tea polyphenols on growth and cellular adherence of an oral bacterium, Porphyromonas gingivalis. Sakanaka, S., et al. Biosci. Biotechnol. Biochem. 60, 745-749, (1996)

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ESR study on the structure-antioxidant activity relationship of tea catechins and their epimers. Guo, Q. Biochim. Biophys. Acta 1427, 13-23, (1999)

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Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids. Deniz Tasdemir et al J. Med. Chem. 49, 3345-53, (2006)

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An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds. Yunbao Liu et al J. Nat. Prod. 73, 1193-5, (2010)

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Profiles and α-amylase inhibition activity of proanthocyanidins in unripe Manilkara zapota (chiku). Wang H, Liu T, Song L, et al. J. Agric. Food Chem. 60(12), 3098-104, (2012)

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Catechin gallates are NADP+-competitive inhibitors of glucose-6-phosphate dehydrogenase and other enzymes that employ NADP+ as a coenzyme. Eui Seok Shin et al Bioorg. Med. Chem. 16, 3580-6, (2008)

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Isolation and characterization of rat intestinal bacteria involved in biotransformation of (-)-epigallocatechin. Takagaki A, Kato Y, and Nanjo F Arch. Microbiol. 196(10), 681-95, (2014)

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[Integrated pharmacokinetic study of multiple effective components of tea polyphenols and its correlation with anti-free radical pharmacodynamics in rats]. Li QS, Xi H, Han GZ, et al. Yao Xue Xue Bao 47(7), 863-9, (2012)

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A proprietary topical preparation containing EGCG-stearate and glycerin with inhibitory effects on herpes simplex virus: case study. Zhao M, Jiang J, Zheng R, et al. Inflamm. Allergy Drug Targets 11(5), 364-8, (2012)

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Bioactivity-guided identification and cell signaling technology to delineate the lactate dehydrogenase A inhibition effects of Spatholobus suberectus on breast cancer. Wang Z, Wang D, Han S, et al. PLoS ONE 8(2), e56631, (2013)

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EGCG suppresses prostate cancer cell growth modulating acetylation of androgen receptor by anti-histone acetyltransferase activity. Lee YH, Kwak J, Choi HK, et al. Int. J. Mol. Med. 30(1), 69-74, (2012)

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Enantioselective total syntheses of (+)-gallocatechin, (-)-epigallocatechin, and 8-C-ascorbyl-(-)-epigallocatechin. Lin G, Chang L, Liu Y, et al. Chem. Asian J. 8(4), 700-4, (2013)

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Green tea catechin intervention of reactive oxygen species-mediated ERK pathway activation and chronically induced breast cell carcinogenesis. Rathore K, Choudhary S, Odoi A, et al. Carcinogenesis 33(1), 174-83, (2012)

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(-)-Epicatechin gallate prevents alkali-salt mediated fibrillogenesis of hen egg white lysozyme. Ghosh S, Pandey NK, and Dasgupta S Int. J. Biol. Macromol. 54, 90-8, (2013)

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Simultaneous ingestion of dietary proteins reduces the bioavailability of galloylated catechins from green tea in humans. Egert S, Tereszczuk J, Wein S, et al. Eur. J. Nutr. 52(1), 281-8, (2013)

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Polyphenol content of plasma and litter after the oral administration of green tea and tea polyphenols in chickens. Zhou YB, Wan XC, Shang YY, et al. J. Agric. Food Chem. 60(7), 1619-27, (2012)

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A new norisoprenoid and other compounds from Fuzhuan brick tea. Luo ZM, Ling TJ, Li LX, et al. Molecules 17(3), 3539-46, (2012)

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Effect of polymerization on antioxidant and xanthine oxidase inhibitory potential of sea buckthorn (H. rhamnoides) proanthocyanidins. Arimboor R and Arumughan C J. Food Sci. 77(10), C1036-41, (2012)

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Aminoglycosylation can enhance the G-quadruplex binding activity of epigallocatechin. Bai LP, Ho HM, Ma DL, et al. PLoS ONE 8(1), e53962, (2013)

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Green tea catechins increase the force of contraction in isolated Guinea pig atrial muscle preparations by increasing the amplitude of intracellular ca(2+) concentration. Sasaki T, Kamata R, Ueno S, et al. J. Vet. Med. Sci. 74, 1603-1608, (2012)

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Radical-scavenging activity of dietary phytophenols in combination with co-antioxidants using the induction period method. Kadoma Y and Fujisawa S Molecules 16(12), 10457-70, (2011)

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Inactivation of prolyl hydroxylase domain (PHD) protein by epigallocatechin (EGCG) stabilizes hypoxia-inducible factor (HIF-1α) and induces hepcidin (Hamp) in rat kidney. Manalo DJ, Baek JH, Buehler PW, et al. Biochem. Biophys. Res. Commun. 416(3-4), 421-6, (2011)

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Quercetin and epigallocatechin gallate effects on the cell membranes biophysical properties correlate with their antioxidant potential. Margina D, Ilie M, Manda G, et al. Gen. Physiol. Biophys. 31(1), 47-55, (2012)

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Inhibitory mechanism of pancreatic amyloid fibril formation: formation of the complex between tea catechins and the fragment of residues 22-27. Kamihira-Ishijima M, Nakazawa H, Kira A, et al. Biochemistry 51(51), 10167-74, (2012)

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A novel combination of methotrexate and epigallocatechin attenuates the overexpression of pro-inflammatory cartilage cytokines and modulates antioxidant status in adjuvant arthritic rats. Roy S, Sannigrahi S, Vaddepalli RP, et al. Inflammation 35(4), 1435-47, (2012)

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Green tea catechins can bind and modify ERp57/PDIA3 activity. Trnková L, Ricci D, Grillo C, et al. Biochim. Biophys. Acta 1830(3), 2671-82, (2013)

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Incompatibility between propericiazine oral solution and tea-based drink. Ikeda H, Tsuji E, Matsubara T, et al. Chem. Pharm. Bull. 60(9), 1207-11, (2012)

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Enzymatic improvement in the polyphenol extractability and antioxidant activity of green tea extracts. Hong YH, Jung EY, Park Y, et al. Biosci. Biotechnol. Biochem. 77(1), 22-9, (2013)

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[Mechanism of interaction between risperidone and tea catechin (2) influence of presence of galloyl group in catechin on insoluble complex formation with risperidone]. Ikeda H, Moriwaki H, Matsubara T, et al. Yakugaku Zasshi 132(1), 145-53, (2012)

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Gallated form of tea catechin, not nongallated form, increases fecal starch excretion in rats. Unno T, Matsumoto Y, and Yamamoto Y J. Nutr. Sci. Vitaminol. 58(1), 45-9, (2012)

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Proanthocyanidin oligomers isolated from Salacia reticulata leaves potently inhibit pancreatic lipase activity. Koga K, Hisamura M, Kanetaka T, et al. J. Food Sci. 78(1), H105-11, (2013)

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Combination therapy of dexamethasone with epigallocatechin enhances tibiotarsal bone articulation and modulates oxidative status correlates with cartilage cytokines expression in the early phase of experimental arthritis. Roy S, Sannigrahi S, Ghosh B, et al. Eur. J. Pharmacol. 698(1-3), 444-54, (2013)

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EGCG inhibits recepteur d'origine nantais expression by suppressing Egr-1 in gastric cancer cells. Park JS, Khoi PN, Joo YE, et al. Int. J. Oncol. 42(3), 1120-6, (2013)

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