Epigallocatechin gallate

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"EGCG" redirects here. For the software, see Extended GCG.
Epigallocatechin gallate
IUPAC name

[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl] 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 N
PubChem 65064
ChemSpider 58575 YesY
MeSH Epigallocatechin+gallate
ChEBI CHEBI:4806 YesY
ChEMBL CHEMBL297453 YesY
Jmol-3D images Image 1
Properties
Molecular formula C22H18O11
Molar mass 458.37 g mol−1
Appearance
Solubility in water soluble[vague][1]
Solubility soluble in ethanol, DMSO, dimethyl formamide[1] at about 20 g/l[2]
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 tea, but not black tea; during black tea production, the catechins are converted to theaflavins and thearubigins.[3] In a high temperature environment, an epimerization change is more likely to occur; however as exposure to boiling water for 30 straight minutes leads to only 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 increased only slightly.[4]

EGCG can be found in many supplements.

Contents

Research on potential therapeutic uses[edit]

EGCG has been the subject of a number of studies investigating its potential use as a therapeutic for a broad range of disorders:

HIV[edit]

A large amount of research has been conducted 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.[5][6][7] 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.[8]

Cancer[edit]

There is increasing evidence to show that EGCG – along with other flavonoids – can be beneficial in treating brain,[9] prostate,[10][11] cervical[12] and bladder[13] cancers. EGCG has been shown to bind and inhibit the anti-apoptotic protein Bcl-xl,[14] which has been implicated in both cancer cell and normal cell survival.[15]

Chronic fatigue syndrome[edit]

Research at Panjab University Chandigarh found that EGCG is effective in various mouse models of chronic fatigue syndrome.[16][17][18]


Sjögren's syndrome[edit]

Research at Medical College of Georgia found that EGCG was effective in a mouse model of Sjögren's syndrome.[19]

Endometriosis[edit]

Xu et al. found that EGCG reduce lesion size in a mouse model of endometriosis.[20]

Spinal muscular atrophy[edit]

Sakla and Lorson found that EGCG increases the number of SMN transcripts in spinal muscular atrophy cells, most probably through modulation of alternative splicing.[21]

Neurodegeneration[edit]

EGCG is a natural chelator and has been shown to reduce iron-accumulation in instances of neurodegenerative diseases like dementia, Alzheimer's, and Parkinson's.[22] Parc de Salut Mar and Instituto Hospital del Mar de Investigaciones Médicas in Spain are conducting a clinical trial of EGCG as a potential treatment for intellectual impairment in people with Down Syndrome and Fragile X[23]

Cannabinoid 1 receptor, CB1 receptor Activity[edit]

EGCG has a binding affinity of Ki=33.6μM towards the first cannabinoid receptor, CB1.[24]

Periapical lesions[edit]

There are in vitro data about theurapeutic potential of EGCG in periapical periodontitis.[25]

Drug interactions[edit]

A 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.[26] 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.[26] EGCG may reduce the bioavailability of the drug sunitinib when they are taken together.[27] EGCG was also found to induce apoptosis in endometrial carcinoma cell line (Ishikawa cells and human primary endometrial carcinoma cells) via ROS generation and p-38 activation.2012 Manohar et al., J Nutr Biochem. 2012 Sep 5 [Epub ahead of print]

Carcinogenic potential[edit]

EGCG was, among other tea polyphenols, found to be a strong topoisomerase inhibitor, similar to some chemotherapeutic anticancer drugs, for example, etoposide and doxorubicin.[28][29][30][31][32] 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.[33][34][35] Maternal consumption of tea or coffee during pregnancy may elevate the risk of childhood malignant central nervous system (CNS) tumours through unknown mechanisms.[36]

Spectral data[edit]

UV spectrum
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−1
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+H]+ m/z : 459

See also[edit]

References[edit]

  1. ^ a b http://chemicalland21.com/lifescience/foco/%28-%29-EPIGALLOCATECHIN%20GALLATE.htm
  2. ^ http://www.caymanchem.com/pdfs/70935.pdf
  3. ^ 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.
  4. ^ Wang R, Zhou W, Jiang X (April 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. 
  5. ^ Williamson MP, McCormick TG, Nance CL, Shearer WT (December 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. 
  6. ^ Hamza A, Zhan CG (February 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. 
  7. ^ Yamaguchi K, Honda M, Ikigai H, Hara Y, Shimamura T (January 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. 
  8. ^ Nance CL, Shearer WT (November 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. 
  9. ^ Das A, Banik NL, Ray SK (November 2009). "Flavonoids activated caspases for apoptosis in human glioblastoma T98G and U87MG cells but not in human normal astrocytes". Cancer 116 (1): 164–76. doi:10.1002/cncr.24699. PMC 3159962. PMID 19894226. 
  10. ^ Hsieh TC, Wu JM (October 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. 
  11. ^ Bettuzzi S, Brausi M, Rizzi F, Peracchia G, Corti A (January 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". American Associaation for Cancer Research 66 (2): 1234–1240. 
  12. ^ Qiao Y, Cao J, Xie L, Shi X (September 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. 
  13. ^ Philips BJ, Coyle CH, Morrisroe SN, Chancellor MB, Yoshimura N (August 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. 
  14. ^ Leone M, Zhai D, Sareth S, Kitada S, Reed JC, Pellecchia M (December 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. 
  15. ^ Cherbonnel-Lasserre C, Dosanjh MK (October 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. 
  16. ^ Sachdeva, A K; Kuhad, A; Chopra, K (2011). "Epigallocatechin gallate ameliorates behavioral and biochemical deficits in rat model of load-induced chronic fatigue syndrome". Brain Research Bulletin 86 (3–4): 165–72. doi:10.1016/j.brainresbull.2011.06.007. PMID 21821105. 
  17. ^ Sachdeva, A K; Kuhad, A; Tiwari, V; Arora, V; Chopra, K (2010). "Protective effect of epigallocatechin gallate in murine water-immersion stress model of chronic fatigue syndrome". Basic & Clinical Pharmacology & Toxicology 106 (6): 490–96. doi:10.1111/j.1742-7843.2009.00525.x. PMID 20088847. 
  18. ^ Sachdeva, A K; Kuhad, A; Tiwari, V; Chopra, K (2009). "Epigallocatechin gallate ameliorates chronic fatigue syndrome in mice: behavioral and biochemical evidence". Behavioural Brain Research 205 (2): 414–20. doi:10.1016/j.bbr.2009.07.020. PMID 1964314. 
  19. ^ Gillespie, K; Kodani, I; Dickinson, DP; Ogbureke, KU; Camba, AM; Wu, M; Looney, S; Chu, TC et al. (2008). "Effects of oral consumption of the green tea polyphenol EGCG in a murine model for human Sjogren's syndrome, an autoimmune disease". Life Sciences 83 (17–18): 581–8. doi:10.1016/j.lfs.2008.08.011. PMC 2701648. PMID 18809413. 
  20. ^ Xu, Hui; Becker, Christian M.; Lui, Wai Ting; Chu, Ching Yan; Davis, Tina N.; Kung, Andrew L.; Birsner, Amy E.; d’Amato, Robert J. et al. (2011). "Green tea epigallocatechin-3-gallate inhibits angiogenesis and suppresses vascular endothelial growth factor C/vascular endothelial growth factor receptor 2 expression and signaling in experimental endometriosis in vivo". Fertility and Sterility 96 (4): 1021–8. doi:10.1016/j.fertnstert.2011.07.008. PMID 21821246. 
  21. ^ Sakla, M. S.; Lorson, C. L. (2007). "Induction of full-length survival motor neuron by polyphenol botanical compounds". Human Genetics 122 (6): 635–643. doi:10.1007/s00439-007-0441-0. PMID 17962980.  edit
  22. ^ Bai, Yun; Yanyan Wang, Maoquan Li, Xueqing Xu, Min Song, Huansheng Tao, (April 2012). "Green tea epigallocatechin-3-gallate (EGCG) promotes neural progenitor cell proliferation and sonic hedgehog pathway activation during adult hippocampal neurogenesis". You have free access to this content Molecular Nutrition & Food Research 56: 1292. doi:10.1002/mnfr.201200035. 
  23. ^ Staff, IMM. Utilización de la epigalocatequina galato (EGCG) para modular Dyrk1A y APP y evaluar su impacto sobre el rendimiento cognitivo en pacientes con síndrome de Down (SD) English translation - Using epigallocatechin gallate (EGCG) to modulate Dyrk1A and APP and evaluate its impact on cognitive performance in patients with Down syndrome (DS) Page Accessed June 7, 2013
  24. ^ PMID=19897346
  25. ^ Lee, Y. L.; Hong, C. Y.; Kok, S. H.; Hou, K. L.; Lin, Y. T.; Chen, M. H.; Wang, C. C.; Lin, S. K. (2009). "An Extract of Green Tea, Epigallocatechin-3-Gallate, Reduces Periapical Lesions by Inhibiting Cysteine-rich 61 Expression in Osteoblasts". Journal of Endodontics 35 (2): 206–211. doi:10.1016/j.joen.2008.11.015. PMID 19166774.  edit
  26. ^ a b Neith, Katie. "Green tea blocks benefits of cancer drug, study finds". Retrieved 2009-02-04. 
  27. ^ 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
  28. ^ Neukam, K.; Pastor, N.; Cortés, F. (Jun 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. 
  29. ^ Berger, SJ.; Gupta, S.; Belfi, CA.; Gosky, DM.; Mukhtar, H. (Oct 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. 
  30. ^ Suzuki, K.; Yahara, S.; Hashimoto, F.; Uyeda, M. (Sep 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. 
  31. ^ Bandele, OJ.; Osheroff, N. (Apr 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. 
  32. ^ Bandele, OJ.; Osheroff, N. (May 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. 
  33. ^ Paolini, M.; Sapone, A.; Valgimigli, L. (Jun 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. 
  34. ^ Strick, R.; Strissel, PL.; Borgers, S.; Smith, SL.; Rowley, JD. (Apr 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. 
  35. ^ Ross, JA. (Apr 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. 
  36. ^ Plichart, M.; Menegaux, F.; Lacour, B.; Hartmann, O.; Frappaz, D.; Doz, F.; Bertozzi, AI.; Defaschelles, AS. et al. (Aug 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. 
Food antioxidants
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