Epigallocatechin gallate - Misplaced Pages

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Epigallocatechin gallate
Names

IUPAC name 3,4,5-trihydroxybenzoate
Preferred IUPAC name (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Other names (-)-Epigallocatechin gallate
Identifiers
CAS Number	989-51-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:4806
ChEMBL	ChEMBL297453
ChemSpider	58575
ECHA InfoCard	100.111.017
MeSH	Epigallocatechin+gallate
PubChem CID	65064
CompTox Dashboard (EPA)	DTXSID1029889
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/s1Key: WMBWREPUVVBILR-WIYYLYMNSA-N InChI=1/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/s1Key: WMBWREPUVVBILR-WIYYLYMNBM
SMILES O=C(O2Cc3c(O2c1cc(O)c(O)c(O)c1)cc(O)cc3O)c4cc(O)c(O)c(O)c4
Properties
Chemical formula	C₂₂H₁₈O₁₁
Molar mass	458.372 g/mol
Appearance
Solubility in water	soluble
Solubility	soluble in ethanol, DMSO, dimethyl formamide at about 20 g/l
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Epigallocatechin gallate (EGCG), also known as epigallocatechin 3-gallate, is the ester of epigallocatechin and gallic acid, and is a type of catechin.

EGCG is the most abundant catechin in tea and is a potent antioxidant that may have therapeutic applications in the treatment of many disorders (e.g. cancer). It is found in green - but not black tea because during black tea production, the catechins are converted to theaflavins and thearubigins. In a high temperature environment, an epimerization change is more likely to occur; however as exposure to boiling water for 30 straight minutes only leads to a 12.4% reduction in the total amount of EGCG, the amount lost in a brief exposure is insignificant. In fact, even when special conditions were used to create temperatures well-above that of boiling water, the amount lost scaled up only slightly.

EGCG can be found in many supplements.

EGCG and HIV

There has been research investigating the benefit of EGCG from green tea in the treatment of HIV infection, where EGCG has been shown to reduce plaques related to AIDS-related dementia in the laboratory, as well as block gp120. However, these effects have yet to be confirmed in live human trials, and it does not imply that green tea will cure or block HIV infection, but it may help regulate viral load as long as it is not involved in adverse drug reactions. The concentrations of EGCG used in the studies could not be reached by drinking green tea. More study into EGCG and HIV is currently underway.

EGCG and Cancer

There is increasing evidence to show that EGCG – along with other flavonoids – can be beneficial in treating brain, prostate, cervical and bladder cancers. EGCG has been shown to bind and inhibit the anti-apoptotic protein Bcl-xl, which has been implicated in both cancer cell and normal cell survival.

EGCG and Sjögren's syndrome

According to the research led at Medical College of GeorgiaCite error: A <ref> tag is missing the closing </ref> (see the help page).

Drug Interactions

A recent study using mouse models at the University of Southern California showed that, in contrast to the myriad benefits commonly associated with green tea and green tea extract (GTE), EGCG binds with the anti-cancer drug Velcade, significantly reducing its bioavailability and thereby rendering it therapeutically useless. Dr. Schönthal, who headed the study, suggests that consumption of green tea and GTE products be strongly contraindicated for patients undergoing treatment for multiple myeloma and mantle cell lymphoma. EGCG has a slight stimulatory effect due to it increasing adrenaline levels.Epigallocatechin-3-gallate, may reduce the bioavaialbilty of the drug sunitinib when they are taken together.

Carcinogenic potential

EGCG was, among other tea polyphenols, found to be a strong topoisomerase inhibitor, similar to some chemotherapeutic anticancer drugs, for example, etoposide and doxorubicin. This property might be responsible for observed anticarcinogenic effects; however, there is also a carcinogenic potential. High intake of polyphenolic compounds during pregnancy is suspected to increase risk of neonatal leukemia. Bioflavonoid supplements should not be used by pregnant women. Maternal consumption of tea or coffee during pregnancy may elevate the risk of childhood malignant central nervous system (CNS) tumours through unknown mechanisms.

Spectral data

UV-Vis
Retention time	34.5 min (C₁₈ RP, Acetonitrile 80%)
Lambda-max	274 and 240 nm (see picture)
Extinction coefficient
IR
Major absorption bands	cm
NMR
Proton NMR (500 MHz, CD3OD): d : doublet, dd : doublet of doublets, m : multiplet, s : singlet	δ :
Carbon-13 NMR
Other NMR data
MS
Masses of main fragments	ESI-MS + m/z : 459

References

^ http://chemicalland21.com/lifescience/foco/%28-%29-EPIGALLOCATECHIN%20GALLATE.htm
http://www.caymanchem.com/pdfs/70935.pdf
Lorenz, M., Urban, J. (January 2009) "Green and Black Tea are Equally Potent Stimuli of NO Production and Vasodilation: New Insights into Tea Ingredients Involved". "Basic Research in Cardiology" "'104" (1): 100-110.
Wang R, Zhou W, Jiang X (2008). "Reaction kinetics of degradation and epimerization of epigallocatechin gallate (EGCG) in aqueous system over a wide temperature range". J. Agric. Food Chem. 56 (8): 2694–701. doi:10.1021/jf0730338. PMID 18361498. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
Williamson MP, McCormick TG, Nance CL, Shearer WT (2006). "Epigallocatechin gallate, the main polyphenol in green tea, binds to the T-cell receptor, CD4: Potential for HIV-1 therapy". The Journal of Allergy and Clinical Immunology. 118 (6): 1369–74. doi:10.1016/j.jaci.2006.08.016. PMID 17157668. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
Hamza A, Zhan CG (2006). "How can (-)-epigallocatechin gallate from green tea prevent HIV-1 infection? Mechanistic insights from computational modeling and the implication for rational design of anti-HIV-1 entry inhibitors". The Journal of Physical Chemistry. B. 110 (6): 2910–7. doi:10.1021/jp0550762. PMID 16471901. {{cite journal}}: Unknown parameter |month= ignored (help)
Yamaguchi K, Honda M, Ikigai H, Hara Y, Shimamura T (2002). "Inhibitory effects of (-)-epigallocatechin gallate on the life cycle of human immunodeficiency virus type 1 (HIV-1)". Antiviral Research. 53 (1): 19–34. doi:10.1016/S0166-3542(01)00189-9. PMID 11684313. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
Nance CL, Shearer WT (2003). "Is green tea good for HIV-1 infection?". The Journal of Allergy and Clinical Immunology. 112 (5): 851–3. doi:10.1016/j.jaci.2003.08.048. PMID 14610469. {{cite journal}}: Unknown parameter |month= ignored (help)
Das A, Banik NL, Ray SK (2009). "Flavonoids activated caspases for apoptosis in human glioblastoma T98G and U87MG cells but not in human normal astrocytes". Cancer. 116 (1): NA. doi:10.1002/cncr.24699. PMC 3159962. PMID 19894226. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
Hsieh TC, Wu JM (2009). "Targeting CWR22Rv1 prostate cancer cell proliferation and gene expression by combinations of the phytochemicals EGCG, genistein, and quercetin". Anticancer Research. 29 (10): 4025–32. PMID 19846946. {{cite journal}}: Unknown parameter |month= ignored (help)
Bettuzzi S, Brausi M, Rizzi F, Peracchia G, Corti A (2006). "Chemoprevention of Human Prostate Cancer by Oral Administration of green Tea Catechins in Volunteers with High-Grade Prostate Intraepithelial Neoplasia: A Preliminary Report from a One-Year Proof-of-Principle Study" (PDF). American Associaation for Cancer Research. 66 (2): 1234–1240. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
Qiao Y, Cao J, Xie L, Shi X (2009). "Cell growth inhibition and gene expression regulation by (-)-epigallocatechin-3-gallate in human cervical cancer cells". Archives of Pharmacal Research. 32 (9): 1309–15. doi:10.1007/s12272-009-1917-3. PMID 19784588. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
Philips BJ, Coyle CH, Morrisroe SN, Chancellor MB, Yoshimura N (2009). "Induction of apoptosis in human bladder cancer cells by green tea catechins". Biomedical Research. 30 (4): 207–15. doi:10.2220/biomedres.30.207. PMID 19729851. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
Leone M, Zhai D, Sareth S, Kitada S, Reed JC, Pellecchia M (2003). "Cancer prevention by tea polyphenols is linked to their direct inhibition of antiapoptotic Bcl-2-family proteins". Cancer Research. 63 (23): 8118–21. PMID 14678963. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
Cherbonnel-Lasserre C, Dosanjh MK (1997). "Suppression of apoptosis by overexpression of Bcl-2 or Bcl-xL promotes survival and mutagenesis after oxidative damage". Biochimie. 79 (9–10): 613–7. doi:10.1016/S0300-9084(97)82011-1. PMID 9466700. {{cite journal}}: Unknown parameter |month= ignored (help)
^ Neith, Katie. "Green tea blocks benefits of cancer drug, study finds". Retrieved 2009-02-04.
"Examine.com: Green Tea Catechins".
Ge J, Tan BX, Chen Y, Yang L, Peng XC, Li HZ, Lin HJ, Zhao Y, Wei M, Cheng K, Li LH, Dong H, Gao F, He JP, Wu Y, Qiu M, Zhao YL, Su JM, Hou JM, Liu JY.,"Interaction of green tea polyphenol epigallocatechin-3-gallate with sunitinib: potential risk of diminished sunitinib bioavailability", J Mol Med (Berl). 2011 Jun;89(6):595-602
Neukam, K.; Pastor, N.; Cortés, F. (2008). "Tea flavanols inhibit cell growth and DNA topoisomerase II activity and induce endoreduplication in cultured Chinese hamster cells". Mutat Res. 654 (1): 8–12. doi:10.1016/j.mrgentox.2008.03.013. PMID 18541453. {{cite journal}}: Unknown parameter |month= ignored (help)
Berger, SJ.; Gupta, S.; Belfi, CA.; Gosky, DM.; Mukhtar, H. (2001). "Green tea constituent (-)-epigallocatechin-3-gallate inhibits topoisomerase I activity in human colon carcinoma cells". Biochem Biophys Res Commun. 288 (1): 101–5. doi:10.1006/bbrc.2001.5736. PMID 11594758. {{cite journal}}: Unknown parameter |month= ignored (help)
Suzuki, K.; Yahara, S.; Hashimoto, F.; Uyeda, M. (2001). "Inhibitory activities of (-)-epigallocatechin-3-O-gallate against topoisomerases I and II". Biol Pharm Bull. 24 (9): 1088–90. doi:10.1248/bpb.24.1088. PMID 11558576. {{cite journal}}: Unknown parameter |month= ignored (help)
Bandele, OJ.; Osheroff, N. (2008). "(-)-Epigallocatechin gallate, a major constituent of green tea, poisons human type II topoisomerases". Chem Res Toxicol. 21 (4): 936–43. doi:10.1021/tx700434v. PMC 2893035. PMID 18293940. {{cite journal}}: Unknown parameter |month= ignored (help)
Bandele, OJ.; Osheroff, N. (2007). "Bioflavonoids as poisons of human topoisomerase II alpha and II beta". Biochemistry. 46 (20): 6097–108. doi:10.1021/bi7000664. PMC 2893030. PMID 17458941. {{cite journal}}: Unknown parameter |month= ignored (help)
Paolini, M.; Sapone, A.; Valgimigli, L. (2003). "Avoidance of bioflavonoid supplements during pregnancy: a pathway to infant leukemia?". Mutat Res. 527 (1–2): 99–101. doi:10.1016/S0027-5107(03)00057-5. PMID 12787918. {{cite journal}}: Unknown parameter |month= ignored (help)
Strick, R.; Strissel, PL.; Borgers, S.; Smith, SL.; Rowley, JD. (2000). "Dietary bioflavonoids induce cleavage in the MLL gene and may contribute to infant leukemia". Proc Natl Acad Sci U S A. 97 (9): 4790–5. doi:10.1073/pnas.070061297. PMC 18311. PMID 10758153. {{cite journal}}: Unknown parameter |month= ignored (help)
Ross, JA. (2000). "Dietary flavonoids and the MLL gene: A pathway to infant leukemia?". Proc Natl Acad Sci U S A. 97 (9): 4411–3. doi:10.1073/pnas.97.9.4411. PMC 34309. PMID 10781030. {{cite journal}}: Unknown parameter |month= ignored (help)
Plichart, M.; Menegaux, F.; Lacour, B.; Hartmann, O.; Frappaz, D.; Doz, F.; Bertozzi, AI.; Defaschelles, AS.; Pierre-Kahn, A. (2008). "Parental smoking, maternal alcohol, coffee and tea consumption during pregnancy and childhood malignant central nervous system tumours: the ESCALE study (SFCE)". Eur J Cancer Prev. 17 (4): 376–83. doi:10.1097/CEJ.0b013e3282f75e6f. PMC 2746823. PMID 18562965. {{cite journal}}: Unknown parameter |month= ignored (help)

v t e Antioxidants
Food antioxidants	6-Hydroxymelatonin Acetyl-L-carnitine (ALCAR) Alpha-lipoic acid (ALA) Ascorbic acid (vitamin C) Carotenoids (vitamin A) Curcumin Edaravone Polyphenols Glutathione Hydroxytyrosol L-carnitine Ladostigil Melatonin Mofegiline N-Acetylcysteine (NAC) N-Acetylserotonin (NAS) Oleocanthal Oleuropein Rasagiline Resveratrol Selegiline Selenium Tocopherols (vitamin E) Tocotrienols (vitamin E) Tyrosol Ubiquinone (coenzyme Q) Uric acid
Fuel antioxidants	Butylated hydroxyanisole Butylated hydroxytoluene 2,6-Di-tert-butylphenol 1,2-Diaminopropane 2,4-Dimethyl-6-tert-butylphenol Ethylenediamine
Measurements	Folin method ORAC TEAC FRAP

Antiviral drugs: antiretroviral drugs used against HIV (primarily J05)

Capsid inhibitors

Lenacapavir (LEN)

Entry/fusion inhibitors
(Discovery and development)

Integrase inhibitors
(Integrase strand transfer inhibitors (INSTI))

Maturation inhibitors

Protease Inhibitors (PI)
(Discovery and development)

1 generation	Amprenavir (APV) Fosamprenavir (FPV) Indinavir (IDV) Lopinavir (LPV) Nelfinavir (NFV) Ritonavir (RTV) Saquinavir (SQV)
2 generation	Atazanavir (ATV)° Darunavir (DRV)° Tipranavir (TPV) TMC-310911

Reverse-transcriptase
inhibitors (RTIs)

Nucleoside and
nucleotide (NRTI)

Non-nucleoside (NNRTI)
(Discovery and development)

1 generation	Efavirenz (EFV) Nevirapine (NVP) Delavirdine (DLV)
2 generation	diarylpyrimidines Dapivirine (DPV) Etravirine (ETR) Rilpivirine (RPV) Doravirine (DOR) Elsulfavirine (ESV)

Combined formulations

Pharmacokinetic boosters

Experimental agents

Uncoating inhibitors	TRIM5alpha (gene)
Transcription inhibitors	Tat antagonists
Translation inhibitors	Trichosanthin
BNAbs	Elipovimab
Other	Abzyme BIT225 Calanolide A Ceragenin Cyanovirin-N Diarylpyrimidines Epigallocatechin gallate (EGCG) Foscarnet Fosdevirine Griffithsin Hydroxycarbamide KP-1461 Miltefosine Portmanteau inhibitors Scytovirin Seliciclib Synergistic enhancers Tre recombinase Zinc finger protein transcription factor
Failed agents	Aplaviroc Atevirdine Brecanavir Capravirine Dexelvucitabine Droxinavir Lasinavir Emivirine Lersivirine Lodenosine Loviride Mozenavir Palinavir Telinavir

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

°DHHS recommended initial regimen options. Formerly or rarely used agent.

v t e Flavan-3-ols and their glycosides
Flavan-3-ols	Afzelechin Catechin (Epicatechin) Epicatechin gallate Epigallocatechin Fisetinidol Gallocatechin Guibourtinidol Mesquitol Oritin Robinetinidol
O-methylated flavan-3ols	Meciadanol (3-O-methylcatechin) Ourateacatechin (4′-O-methyl-(−)-epigallocatechin)
Glycosides	Arthromerin A (Afzelechin-3-O-β-D-xylopyranoside) Arthromerin B (Afzelechin-3-O-β-D-glucopyranoside) Catechin-3-O-glucoside Catechin-3'-O-glucoside Catechin-4'-O-glucoside Catechin-5-O-glucoside Catechin-7-O-glucoside (+)-Catechin 7-O-β-D-xylopyranoside Epicatechin-3′-O-glucoside Glochiflavanoside A, B, C D Polydine ((+)-catechin 7-O-α-L-arabinoside) Symplocoside (3'-O-methyl-(-)-epicatechin 7-O-β-D-glucopyranoside)
Acetylated	Phylloflavan
Gallate esters	Epigallocatechin gallate Gallocatechin gallate
Misc.	Thearubigins

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