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J Agric Food Chem. 2003 Dec 3;51(25):7318-25.

Cleavage products of lycopene produced by in vitro oxidations: characterization and mechanisms of formation.

Author information

1
UMR Safety and Quality of Plant Products, INRA, Domaine Saint Paul, Site Agroparc, 84914 Avignon Cedex 9, France. caris@avignon.inra.fr

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.

PMID:
14640578
DOI:
10.1021/jf034735+
[Indexed for MEDLINE]

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