Malondialdehyde trapping by food phenolics

Abstract

The reactions between malondialdehyde and 2,5-dimethylresorcinol, orcinol, olivetol, and alkylresocinols were studied in an attempt to investigate both if this lipid oxidation product is trapped by phenolics analogously to other reactive carbonyls and to elucidate the chemical structures of the produced adducts. After being formed, malondialdehyde is both partially fractionated to acetaldehyde and oligomerized into dimers and trimers. All these compounds react with phenolics producing three main kinds of derivatives: 5(or 7)-alkyl-7(or 5)-hydroxy-4-methyl-4H-chromene-3-carbaldehydes, 7-alkyl-9-hydroxy-6H-2,6-methanobenzo[d][1,3]dioxocine-5-carbaldehydes, and 4-(3-formylphenyl)-7-hydroxy-4H-chromene-3-carbaldehydes. A total of twenty-four adducts were isolated by semipreparative high-performance liquid chromatography (HPLC) and characterized by mono- and bi-dimensional nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS). Reaction pathways to explain the formation of all these compounds are proposed. Obtained results show that phenolics can trap malondialdehyde producing stable derivatives. The function(s) that such derivatives can play in foods remain(s) to be elucidated.

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.