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Epigallocatechin gallate

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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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.111.017 Edit this at Wikidata
MeSH Epigallocatechin+gallate
PubChem CID
CompTox Dashboard (EPA)
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 Georgia, EGCG may help protect against some autoimmune diseases, including Sjögren's syndrome. Research results may suggest that EGCG (e.g,. in green tea) can turn on the body’s defense system against TNF-alpha proteins, which are involved in systemic inflammation. Department of Periodontology, US Army Fort Gordon, Fort Gordon, GA, USA Effects of oral consumption of the green tea polyphenol EGCG in a murine model for human Sjogren's syndrome, an autoimmune disease. PMID: 18809413 PMCID: PMC2701648

EGCG and endometriosis

Xu et al. found that antiangiogenic effects of EGCG inhibits the growth of blood vessels and thus reduces lesion size in experimental endometriosis (mouse model).

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 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
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

See also

References

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  2. http://www.caymanchem.com/pdfs/70935.pdf
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  4. 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)
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  7. 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)
  8. 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)
  9. 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)
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  16. doi:10.1016/j.fertnstert.2011.07.008
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  18. "Examine.com: Green Tea Catechins".
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