Structural Modification of Epigallocatechin-3-gallate to (2R,3R)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chroman-3-yl l-valinate in Four Steps

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...

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Bibliographic Details
Published inMolBank Vol. 2024; no. 2; p. M1826
Main Authors Yu, Xiaoman, Ren, Zimo, Coghi, Paolo, Ng, Jerome P. L.
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 01.06.2024
Subjects
Acids
Antioxidants
Bioavailability
Chromatography
EGCG
Gallic acid
NMR
Nuclear magnetic resonance
Spectrum analysis
structural modification
Valine
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Summary: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.
ISSN:1422-8599
1422-8599
DOI:10.3390/M1826