(-)-Epicatechin gallate - CAS 1257-08-5
Catalog number: 1257-08-5
Category: Inhibitor
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Molecular Formula:
C22H18O10
Molecular Weight:
442.37
COA:
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Targets:
Others
Description:
(−)-Epicatechin gallate (ECG) is a natural catechin with a single galloyl group. Like EGCG, it inhibits the growth of cancer cells and has anti-inflammatory effects. The hydroxyl groups of ECG contribute to its potent antioxidant activity and facilitate the killing of methicillin-resistant strains of S. aureus.
Purity:
>98%
Synonyms:
ECG; Epicatechin gallate; (-)-Epicatechin 3-O-gallate
MSDS:
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InChIKey:
LSHVYAFMTMFKBA-TZIWHRDSSA-N
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
Canonical SMILES:
C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O
1. Separation and characterization of polyphenolics from underutilized byproducts of fruit production (Choerospondias axillaris peels): inhibitory activity of proanthocyanidins against glycolysis enzymes
Qian Li, Jun Chen, Ti Li,* David Julian McClements*. Food Funct.,2015, 6, 3693–3701
This result suggested that the terminal unit was released as catechin, epicatechin, and epicatechin gallate, and the extension units were released as epigallocatechin, catechin, epicatechin and epicatechin gallate phloroglucinol adducts. Thus, the dominant extension unit was epicatechin gallate, followed by epicatechin, while the terminal unit mainly consisted of catechin judging from the HPLC peak intensity. PAs present in different plants show various characteristics of monomeric units. C. Itoa et al. found that PA oligomers from black soybeans consisted only of epicatechin. K. Fernaandez, J. A. Kennedy and E. Agosin had reported that mangosteen pericarp oligomeric PAs mainly consisted of catechin/epicatechin together with a few gallocatechin/epigallocatechin and afzelechin/epiafzelechin units. Other studies have reported that the most widely distributed PAs in plants contain either exclusively procyanidins or a mixture of procyanidins and prodelphinidins (heterogeneous PAs), with prodelphinidins being less common in nature than procyanidins.
2. Application of isothermal titration calorimetry as a tool to study natural product interactions
O. Callies and A. Hern´ andez Daranas*. Nat. Prod. Rep.
Antioxidant activity of polyphenols has found wide application in radioprotection and cancer prevention by scavenging reactive oxygen species. Enzyme inhibition was shown to be involved in the responsible mechanisms. In the investigation carried out by Pal et al., the thermodynamic parameters recorded for the binding of epicatechin, epigallocatechin, epicatechin gallate, and epigallocatechin gallate (Fig. 2B and C) with catalase resulted in negative heats with binding constants between 1.9 and 8.2 × 10-5 M-1, emphasizing that the interactions of all four catechins with catalase are spontaneous and exothermic. The favourable △H values between -1.88 × 10-3 and -3.06 × 10-5 kJ mol-1, and unfavourable -T△S values from 6.19 to 1.00 × 10-5kJ mol-1 showed the implication of hydrogen bonding and electrostatic contributions with polar groups of the protein and the galloyl moiety. Thus, ITC data indicate that the anticancer activity of the evaluated compounds is mainly due to catalase inhibition.
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CAS 1257-08-5 (-)-Epicatechin gallate

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