Epicatechin gallate

Epicatechin gallate
Chemical structure of epicatechin gallate
Chemical structure of 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
ECG
Epicatechin 3-gallate
(−)-Epicatechin-3-O-gallate
Identifiers
CAS Number
  • 1257-08-5 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:70255 ☒N
ChEMBL
  • ChEMBL36327 ☒N
ChemSpider
  • 97034 ☒N
ECHA InfoCard 100.116.252 Edit this at Wikidata
KEGG
  • C22594
PubChem CID
  • 107905
UNII
  • 92587OVD8Z checkY
CompTox Dashboard (EPA)
  • DTXSID70925231 Edit this at Wikidata
InChI
  • 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
Chemical formula
 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).
☒N verify (what is checkY☒N ?)
Infobox references
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

  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): 509–512. doi:10.1016/0031-9422(96)00301-9.
  4. ^ 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.
  5. ^ 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

  • v
  • t
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Receptor
(ligands)
CB1Tooltip Cannabinoid receptor type 1
Agonists
(abridged,
full list)
Inverse agonists
Antagonists
CB2Tooltip Cannabinoid receptor type 2
Agonists
Antagonists
NAGly
(GPR18)
Agonists
Antagonists
GPR55
Agonists
Antagonists
GPR119
Agonists
Transporter
(modulators)
eCBTsTooltip Endocannabinoid transporter
Enzyme
(modulators)
FAAHTooltip Fatty acid amide hydrolase
  • Activators: PDP-EA
MAGL
ABHD6
  • Inhibitors: JZP-169
  • JZP-430
  • KT182
  • KT185
  • KT195
  • KT203
  • LEI-106
  • ML294
  • ML295
  • ML296
  • UCM710
  • WWL-70
ABHD12
Others
  • Others: 2-PG (directly potentiates activity of 2-AG at CB1 receptor)
  • ARN-272 (FAAH-like anandamide transporter inhibitor)
See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)
  • v
  • t
  • e
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others
  • v
  • t
  • e
Flavan-3-ols and their glycosides
Flavan-3-ols
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
Gallate esters
Misc.


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