LIPID MAPS

Structure Database (LMSD)

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Common Name

Epicatechin

Systematic Name

Synonyms

LM ID

LMPK12020003

Formula

C₁₅H₁₄O₆

Exact Mass

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290.07904

Status

Curated

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Classification

Biological Context

(−)-Epicatechin is a polyketide synthase-derived polyphenol flavonoid that has been found in T. cacao and has diverse biological activities.^1,2,3,4,5 It scavenges DPPH radicals in a cell-free assay when used at a concentration of 5 µM.² (−)-Epicatechin inhibits COX-1 (IC50 = 3.2 μM).⁶ It acts synergistically with epigallocatechin gallate to induce apoptosis in, and reduce the proliferation of, PC-9 lung cancer cells when used at a concentration of 200 µM.⁴ (−)-Epicatechin (80 mg/kg) reduces LPS-induced increases in plasma creatinine and urea levels in a rat model of renal inflammation.⁵

This information has been provided by Cayman Chemical

References

1. Waffo-Téguo, P., Hawthorne, M.E., Cuendet, M., et al. Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures. Nutr. Cancer 40(2), 173-179 (2001).

2. 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).

3. Suganuma, M., Okabe, S., Kai, Y., et al. Synergistic effects of (−)-epigallocatechin gallate with (−)-epicatechin, sulindac, or tamoxifen on cancer-preventive activity in the human lung cancer cell line PC-9. Cancer Res. 59(1), 44-47 (1999).

4. Waffo-Téguo, P., Hawthorne, M.E., Cuendet, M., et al. Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures. Nutr. Cancer 40(2), 173-179 (2001).

5. Tauchen, J., Huml, L., Rimpelova, S., et al. Flavonoids and related members of the aromatic polyketide group in human health and disease: Do they really work? Molecules 25(17), 3846 (2020).

6. Prince, P.D., Fischerman, L., Toblli, J.E., et al. LPS-induced renal inflammation is prevented by (−)‐epicatechin in rats. Redox Biol. 11, 342-349 (2017).