Not to be confused with
EGCG .
Epicatechin gallate
Names
IUPAC name
(2R ,3R )-3′,4′,5,7-Tetrahydroxyflavan-3-yl 3,4,5-trihydroxybenzoate
Systematic IUPAC name
(2R ,3R )-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H -1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Other names
Identifiers
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.116.252
KEGG
UNII
InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1
N Key: LSHVYAFMTMFKBA-TZIWHRDSSA-N
N InChI=1/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1
Key: LSHVYAFMTMFKBA-TZIWHRDSBY
O=C(O[C@@H]2Cc3c(O[C@@H]2c1ccc(O)c(O)c1)cc(O)cc3O)c4cc(O)c(O)c(O)c4
Properties
C22 H18 O10
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).
Chemical compound
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 such as Staphylococcus aureus .[ 1] Nevertheless, the compound is significantly degraded by steeping in boiling water, unlike related catechins.[ 4]
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 .[ 5]
References
^ 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 .
^ 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 .
^ Souquet, Jean-Marc; Cheynier, Véronique; Brossaud, Franck; Moutounet, Michel (1996). "Polymeric proanthocyanidins from grape skins". Phytochemistry . 43 (2): 509–512. doi :10.1016/0031-9422(96)00301-9 .
^ Saklar, Sena; Ertas, Erdal; Ozdemir, Ibrahim S.; Karadeniz, Bulent (October 2015). "Effects of different brewing conditions on catechin content and sensory acceptance in Turkish green tea infusions" . Journal of Food Science and Technology . 52 (10): 6639–6646. doi :10.1007/s13197-015-1746-y . PMC 4573099 . PMID 26396411 .
^ 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
Receptor (ligands )
CB1 Tooltip Cannabinoid receptor type 1
Agonists(abridged,full list ) Inverse agonists Antagonists
CB2 Tooltip Cannabinoid receptor type 2
Agonists
2-AG
2-AGE (noladin ether)
3,3'-Diindolylmethane
4-O-Methylhonokiol
α-Amyrin · β-Amyrin
A-796,260
A-834,735
A-836,339
AM-1172
AM-1221
AM-1235
AM-1241
AM-2232
Anandamide
AZ-11713908
Cannabinol
Caryophyllene
CB-13
CBS-0550
CP 55,940
GW-405,833 (L-768,242)
GW-842,166X
HU-308
JTE 7-31
JWH-007
JWH-015
JWH-018
JWH-73
JWH-133
L-759,633
L-759,656
Lenabasum (anabasum)
Magnolol
MDA-19
Nabitan
NADA
Olorinab (APD-371)
PF-03550096
S-444,823
SER-601
Serinolamide A
UR-144
Tedalinab
THC (dronabinol)
THCV
Tetrahydromagnolol
Virodhamine
Antagonists
NAGly (GPR18 )
GPR55
GPR119
Transporter (modulators )
eCBTs Tooltip Endocannabinoid transporter
Enzyme (modulators )
Others
Others: 2-PG (directly potentiates activity of 2-AG at CB1 receptor)
ARN-272 (FAAH-like anandamide transporter inhibitor)
Flavan-3-ols O-methylated flavan-3ols Glycosides Acetylated Gallate esters Misc.