Structural Modification of Epigallocatechin-3-gallate to (2<i>R</i>,3<i>R</i>)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chroman-3-yl <span style="font-variant: small-caps">l</span>-valinate in Four Steps
Xiaoman Yu,
Zimo Ren,
Paolo Coghi,
Jerome P. L. Ng
Affiliations
Xiaoman Yu
Dr. Neher’s Biophysics Laboratory for Innovative Drug Discovery, State Key Laboratory of Quality Research in Chinese Medicine, Macau University of Science and Technology, Macau 999078, China
Zimo Ren
Laboratory for Drug Discovery from Natural Resources & Industrialization, School of Pharmacy, Macau University of Science and Technology, Macau 999078, China
Paolo Coghi
Dr. Neher’s Biophysics Laboratory for Innovative Drug Discovery, State Key Laboratory of Quality Research in Chinese Medicine, Macau University of Science and Technology, Macau 999078, China
Jerome P. L. Ng
Dr. Neher’s Biophysics Laboratory for Innovative Drug Discovery, State Key Laboratory of Quality Research in Chinese Medicine, Macau University of Science and Technology, Macau 999078, China
Tea is a daily drink for most people, and one of its major ingredients, epigallocatechin-3-gallate (EGCG), has been widely recognized as a potent antioxidant with diverse biological activities. However, its low stability and bioavailability hinder its further clinical applications. In this study, we designed and synthesized a novel EGCG-valine derivative 4 by replacing the gallic acid with a valine moiety in four steps. The structural elucidation of derivative 4 was performed using NMR, IR, mass, and UV spectroscopies. Additionally, the physicochemical properties of 4 were predicted by SwissADME, showing improved drug-like parameters and intestinal absorption compared to the parent compound EGCG.
