Targeted filtering reduces the complexity of UHPLC-Orbitrap-HRMS data to decipher polyphenol polymerization

Area of Science:

• Polymer Chemistry
• Analytical Chemistry
• Organic Chemistry

Background:

• Polymeric polyphenols are complex natural compounds.
• Understanding their reactions is crucial for various applications.
• Epicatechin and acetaldehyde reactions are not fully characterized.

Purpose of the Study:

• To investigate the reaction products of epicatechin with acetaldehyde.
• To characterize complex polymeric polyphenols using advanced analytical techniques.
• To explore acid-catalyzed depolymerization and nucleophilic addition reactions.

Main Methods:

• Ultra-High-Performance Liquid Chromatography-High Resolution Mass Spectrometry (UHPLC-HRMS).
• Petroleomics-inspired strategies including Van Krevelen diagrams and Kendrick mass defect filtering.
• Mass fragmentation and phloroglucinolysis for structural elucidation.

Main Results:

• Over 65 compounds were identified from epicatechin-acetaldehyde reactions.
• Homogeneous bridged derivatives up to the undecamer were characterized.
• Novel vinyl, ethanol adducts, xanthene, and xanthylium salt derivatives were discovered.

Conclusions:

• UHPLC-HRMS combined with data analysis strategies effectively characterizes complex polyphenol reactions.
• New reaction pathways and derivative structures were elucidated for epicatechin and acetaldehyde.
• This study provides a foundation for understanding polyphenol modifications and adduct formation.