Carotenoids oxidation products are of interest for their possible biological activity. We obtained and characterized a series of lycopene oxidative cleavage products by oxidizing lycopene with potassium permanganate and by oxygen with a metalloporphyrin catalyst. We then synthesized three series of apo-lycopenoids of different polyene chain lengths and terminal functions. Our synthetic strategy was based on chemical reactions classically used in carotenoid synthesis: the Horner-Wadsworth-Emmons and Wittig condensations, together with reduction, oxidation and saponification reactions for functional group modifications. We determined the antioxidant activity of synthesized and commercial apo-lycopenoids using a home-made lipid peroxidation test mimicking oxidative stress in the gastro-intestinal tract. A mathematical treatment yielding useful kinetic parameters was developed to achieve a quantitative comparison between the investigated antioxidants in order to establish structure-activity relationships. These results allowed us to get insights into the mechanism of possible antioxidant protection of apo-lycopenoids in the gastro-intestinal tract.

Oxidative cleavage products of lycopene: Obtaining and reactivity in a biomimetic experimental model of oxidative stress

243rd National Meeting (2012)

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