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Epicatechin-Diarylboronate Aggregates with Inhibited Auto-oxidation and Stable Antioxidant Activity: Structural
Wenqi Zhao1, Meihuan Yao1, Mengdi Zhang1
1Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, P. R. China.
The Journal of Physical Chemistry. B
|March 4, 2026
Summary
This study developed catechin-diarylboronate (DiarylBA) esters to enhance stability and antioxidant activity. These novel carriers improve catechin (EC) utilization in healthcare by preventing oxidation while retaining ROS scavenging capabilities.
Area of Science:
- Biochemistry
- Materials Science
- Medicinal Chemistry
Background:
- Catechins exhibit valuable antioxidant and reactive oxygen species (ROS) scavenging properties crucial for healthcare.
- Improving catechin stability against autoxidation is essential for their effective therapeutic application.
- Arylboronic acid modification offers a strategy for enhancing catechin stability and controlled release.
Purpose of the Study:
- To develop novel catechin-diarylboronate (DiarylBA) ester self-assembly carriers.
- To evaluate the stability, antioxidant activity, and ROS scavenging efficacy of these modified catechins.
- To investigate the binding thermodynamics, interaction mechanisms, and aggregation behavior of the developed esters.
Main Methods:
- Synthesis of three catechin-diarylboronate (DiarylBA) esters using (-)-epicatechin (EC) and different boronic acid receptors (BTEAB, PyBBA, PyPBA).
- Characterization using spectroscopies (UV-vis, NMR), ROS scavenging assays, Isothermal Titration Calorimetry (ITC), and light scattering.
- Assessment of auto-oxidation inhibition and antioxidant activities across a pH range (6.5-8.5).
Main Results:
- Esterification of EC with DiarylBA effectively inhibited auto-oxidation, even at pH 8.5, while preserving antioxidant activity.
- EC-DiarylBA esters were successfully generated in a pH range from 6.5 to 8.5.
- EC-BTEAB showed direct H2O2 responsiveness, while EC-PyBBA and EC-PyPBA required EC release for H2O2 elimination.
Conclusions:
- Catechin-diarylboronate (DiarylBA) esters represent a promising strategy for enhancing catechin stability and biological activity.
- These modified catechins offer improved potential for medicinal and healthcare applications.
- The developed carriers demonstrate tunable properties for targeted ROS scavenging and therapeutic delivery.
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