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Malondialdehyde trapping by food phenolics.

Rosario Zamora¹, Esmeralda Alcon¹, Francisco J Hidalgo¹

¹Instituto de la Grasa, CSIC, Carretera de Utrera Km 1, Campus Universitario - Edificio 46, 41013 Seville, Spain.

|March 18, 2023

Summary

This summary is machine-generated.

Phenolic compounds can trap malondialdehyde, a lipid oxidation product, forming stable derivatives. Further research is needed to understand the roles of these adducts in food systems.

Keywords:

2,5-Dimethylresorcinol (PubChem ID: 68103)5-Alkylresorcinol (PubChem ID: 85096661)Acetaldehyde (PubChem ID: 177)Carbonyl-amine reactions Carbonyl-phenol reactions Food carbonylome Formaldehyde (PubChem ID: 712)Isotopic labelling Lipid oxidation Maillard reaction Malondialdehyde (PubChem ID: 10964)Olivetol (PubChem ID: 10377)Orcinol (PubChem ID: 10436)Reactive carbonyls

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Area of Science:

Food Chemistry
Organic Chemistry
Lipid Oxidation

Background:

Malondialdehyde (MDA) is a reactive carbonyl species formed during lipid oxidation.
Phenolic compounds are known antioxidants that can react with carbonyls.

Purpose of the Study:

To investigate if phenolics trap malondialdehyde (MDA).
To elucidate the chemical structures of adducts formed between MDA and various phenolics.
To propose reaction pathways for adduct formation.

Main Methods:

Reactions of MDA with 2,5-dimethylresorcinol, orcinol, olivetol, and alkylresorcinols.
Isolation of adducts using semipreparative high-performance liquid chromatography (HPLC).
Characterization of adducts using nuclear magnetic resonance (NMR) and mass spectrometry (MS).

Main Results:

MDA reacts with phenolics to form three main classes of derivatives.
Twenty-four stable adducts were isolated and structurally characterized.
Proposed reaction pathways explain the formation of these chromene and methanobenzo[d][1,3]dioxocine derivatives.

Conclusions:

Phenolic compounds effectively trap malondialdehyde, forming stable derivatives.
The biological or functional roles of these MDA-phenolic adducts in food matrices require further investigation.