Epicatechin gallate

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Epicatechin gallate
Chemical structure of epicatechin gallate
Names
IUPAC name
[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
Other names
ECG
Epicatechin 3-gallate
(−)-Epicatechin-3-O-gallate
Identifiers
1257-08-5 YesY
ChEBI CHEBI:70255 N
ChEMBL ChEMBL36327 N
ChemSpider 97034 N
Jmol interactive 3D Image
PubChem 107905
Properties
C22H18O10
Molar mass 442.37 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Epicatechin gallate (ECG) is a flavan-3-ol, a type of flavonoid, present in green tea.[1] It is also reported in buckwheat[2] and in grape.[3]

The tea component epicatechin gallate is being researched because in vitro experiments showed it can reverse methicillin resistance in bacteria like Staphylococcus aureus.[1] If confirmed, this means the combined intake of a tea extract containing this component might also enhance the effectiveness of methicillin treatment against some resistant bacteria in vivo.[citation needed]

Epicatechin, as well as many other flavonoids, has been found to act as a non-selective antagonist of the opioid receptors, albeit with somewhat low affinity.[4]

References[edit]

  1. ^ a b Shiota, S; Shimizu, M; Mizushima, T; Ito, H; Hatano, T; Yoshida, T; Tsuchiya, T (1999). "Marked reduction in the minimum inhibitory concentration (MIC) of beta-lactams in methicillin-resistant Staphylococcus aureus produced by epicatechin gallate, an ingredient of green tea (Camellia sinensis)". Biological & pharmaceutical bulletin 22 (12): 1388–90. doi:10.1248/bpb.22.1388. PMID 10746177. 
  2. ^ Danila, Ana-Maria; Kotani, Akira; Hakamata, Hideki; Kusu, Fumiyo (2007). "Determination of Rutin, Catechin, Epicatechin, and Epicatechin Gallate in BuckwheatFagopyrum esculentumMoench by Micro-High-Performance Liquid Chromatography with Electrochemical Detection". Journal of Agricultural and Food Chemistry 55 (4): 1139–43. doi:10.1021/jf062815i. PMID 17253718. 
  3. ^ Souquet, Jean-Marc; Cheynier, Véronique; Brossaud, Franck; Moutounet, Michel (1996). "Polymeric proanthocyanidins from grape skins". Phytochemistry 43 (2): 509. doi:10.1016/0031-9422(96)00301-9. 
  4. ^ Katavic PL, Lamb K, Navarro H, Prisinzano TE (August 2007). "Flavonoids as opioid receptor ligands: identification and preliminary structure-activity relationships". J. Nat. Prod. 70 (8): 1278–82. doi:10.1021/np070194x. PMC 2265593. PMID 17685652. 

See also[edit]


Flavan-3-ols and their glycosides
Flavan-3-ols
O-methylated flavan-3ols
Glycosides
Acetylated
Misc.


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