Abstract
The aim of this study was to produce in vitro oxidation products of lycopene, which could be possible in vivo metabolites. An oxidation of lycopene with potassium permanganate gave a range of lycopene degradation compounds resulting from the oxidative cleavage of one or two carbon-carbon double bonds. Eleven apo-lycopenals/ones and six apo-carotendials were obtained and tentatively characterized by HPLC-DAD-MS. Apo-11-lycopenal and apo-8,6'-carotendial were isolated and characterized by (1)H NMR for the first time. Lycopene was submitted to an oxidation by atmospheric oxygen catalyzed by a metalloporphyrin, a model system of the active center of cytochrome P450 enzymes. (Z)-Isomers, monoxides, and cleavage compounds of (E)-lycopene were formed. We propose a mechanism of oxidation of lycopene by this system.
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