Synthesis and ribonuclease A inhibition activity of resorcinol and phloroglucinol derivatives of catechin and epicatechin: Importance of hydroxyl groups

The reported ribonuclease A inhibitory activity of the green tea extracts prompted us to synthesize novel catechin/epicatechin based conjugates with resorcinol and phloroglucinol with the aim to increase the number of phenolic OH groups. These are found to be more effective inhibitors of ribonuclease A as compared to catechin and epicatechin thus indicating the importance of number of phenolic OH groups for the inhibition of ribonucleolytic activity. Fluorescence studies have been carried out to evaluate the binding parameters. The protein–ligand docking studies are also performed to gain insight into the protein–polyphenols interactions. The epicatechin based polyphenols 1 and 2 also showed inhibition of angiogenin-induced angiogenesis, as determined by chorioallantoic membrane (CAM) assay.

(A) Lane1: RNA, Lane 2: RNase A + RNA, Lane 3: RNaseA + Epicatechin + RNA, Lane 4: RNase A + 2 + RNA, Lane 5: RNase A + 1 + RNA, Lane 6: RNase A + 3′-CMP + RNA. (B) Lane 1: RNA, Lane 2: RNase A + RNA, Lane 3: RNase A + Catechin + RNA, Lane 4: RNase A + 3 + RNA, Lane 5: RNase A + 4 + RNA.Figure optionsDownload as PowerPoint slide