Exposure of lipid molecules to various free radicals could cause lipid peroxidation and give rise to a wide range of cytotoxic aldehydes. Highly electrophilic a, �-unsaturated aldehydes acrolein (ACR) and 4-hydroxy-trans-2-nonenal (HNE) are intensively studied for their involvement in the development of some neurodegenerative diseases. In this study, some natural polyphenols including flavan-3-ols, theaflavins, cyanomaclurin and dihydrochalcones were found to be capable of trapping ACR and HNE by working as sacrificial nucleophiles in simulated physiological conditions. LC-MS/MS analysis showed that these effective polyphenols formed adducts with ACR and HNE. A major adduct formed from phloretin and ACR was purified and its structure was characterized by LC-MS and NMR spectroscopy as diACR-conjugated phloretin. The chemical nature of interactions between a, �-unsaturated aldehydes and polyphenols was also proposed. Findings of the present study highlighted certain classes of polyphenols as promising sequestering agents of a, �-unsaturated aldehydes to inhibit oxidative stress-associated diseases.

Natural polyphenols as sequestering agents of lipid peroxidation-derived acrolein and 4-hydroxy-<i>trans</i>-2-nonenal

239th National Meeting (2010)

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Natural polyphenols as sequestering agents of lipid peroxidation-derived acrolein and 4-hydroxy-trans-2-nonenal