Some reactive carbonyl species (RCS) are generated as secondary cytotoxic products when polyunsaturated fatty acids (PUFAs) undergo lipid peroxidation. Among the most studied RCS, 4-hydroxy-2-nonenal (4-HNE) is considered as one of the lipid peroxidation biomarkers. The accumulation of this lipid-derived unsaturated reactive aldehyde can covalently modify biomolecules such as DNA, proteins, and phospholipids, leading to various pathological conditions such as cancers, diabetes mellitus, cardiovascular diseases, and other age-related diseases. Dietary polyphenols are believed to scavenge these RCS, but very few studies have been conducted to understand the trapping effects of 4-HNE by dietary polyphenols. This study investigates the interactions between cytotoxic 4-HNE and a major apple flavonoid, phloretin (Ph). The study results establish that phloretin effectively traps 4-HNE by forming covalent adducts. The major adducts were purified, and LC-MS and NMR spectroscopy techniques were used to elucidate their structures as different isomeric forms of mono-4-HNE-conjugated phloretin. The interaction between the phloretin and α,β unsaturated aldehyde was proposed as the Michael addition reaction of the phloretin to the C=C double bond of 4-HNE. Findings from this study pave the way to understand how dietary flavonoids could act as effective scavengers of 4-HNE by working as a sacrificial nucleophile in-vivo and preventing or reducing the risk of chronic diseases that affect the quality of human life.

Trapping effects of  lipid peroxidation product – 4-hydroxynonenal (4-HNE) - by apple flavonoid, phloretin

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ACS Fall 2022

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