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Structure Database (LMSD)

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Common Name

(-)-Epicatechin 3-O-gallate

Systematic Name

(2R)-3,4-Dihydro-2α-(3,4-dihydroxyphenyl)-2H-1-benzopyran-3α,5,7-triol 3-(3,4,5-trihydroxybenzoate)

Synonyms

3-O-Galloylepicatechin
ECG

LM ID

LMPK12020090

Formula

C₂₂H₁₈O₁₀

Exact Mass

Calculate m/z

442.09

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

(−)-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.^1,2,3 The hydroxyl groups of ECG contribute to its potent antioxidant activity and facilitate the killing of methicillin-resistant strains of S. aureus.^4,5

This information has been provided by Cayman Chemical

References

1. Anderson, J.C., McCarthy, R.A., Paulin, S., et al. Anti-staphylococcal activity and β-lactam resistance attenuating capacity of structural analogues of (--)-epicatechin gallate. Bioorg. Med. Chem. Lett. 21(23), 6996-7000 (2011).

2. Du, G.J., Zhang, Z., Wen, X.D., et al. Epigallocatechin gallate (EGCG) is the most effective cancer chemopreventive polyphenol in green tea. Nutrients 4(11), 1679-1691 (2012).

3. Kürbitz, C., Heise, D., Redmer, T., et al. Epicatechin gallate and catechin gallate are superior to epigallocatechin gallate in growth suppression and anti-inflammatory activities in pancreatic tumor cells. Cancer Sci. 102(4), 728-734 (2011).

4. Ravindranath, M.H., Ramasamy, V., Moon, S., et al. Differential growth suppression of human melanoma cells by tea (Camellia sinensis) epicatechins (ECG, EGC and EGCG). Evid. Based Complement. Alternat. Med. 6(4), 523-530 (2009).

5. Xu, J.Z., Yeung, S.Y.V., Chang, Q., et al. Comparison of antioxidant activity and bioavailability of tea epicatechins with their epimers. Br. J. Nutr. 91(6), 873-881 (2004).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Viridiplantae (#33090)

Flavonoid imported from http://metabolomics.jp/

Camellia sinensis (#4442)

Magnoliopsida (#3398)

The catechins of green tea. Part II,
J Chem Soc, 1948

DOI: 10.1039/JR9480002249

String Representations

InChiKey (Click to copy)

LSHVYAFMTMFKBA-TZIWHRDSSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C1(O)C=C2O[C@H](C3C=C(O)C(O)=CC=3)[C@H](OC(C3C=C(O)C(O)=C(O)C=3)=O)CC2=C(O)C=1