title: Cleavage products of lycopene produced by in vitro oxidations: characterization and mechanisms of formation.
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.
authors.affiliation: UMR Safety and Quality of Plant Products, INRA, Domaine Saint Paul, Site Agroparc, 84914 Avignon Cedex 9, France. caris@avignon.inra.fr
authors.forename: Catherine
authors.initials: C
authors.lastname: Caris-Veyrat
authors.forename: Antje
authors.initials: A
authors.lastname: Schmid
authors.forename: Michel
authors.initials: M
authors.lastname: Carail
authors.forename: Volker
authors.initials: V
authors.lastname: Böhm
mesh_terms: D002338:Carotenoids / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D000077276:Lycopene; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008665:Metalloporphyrins / Q000737:chemistry; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry; D011196:Potassium Permanganate / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry
chemical_list: D008665:Metalloporphyrins; D011196:Potassium Permanganate; D002338:Carotenoids; D012428:Ruthenium; D010100:Oxygen; D000077276:Lycopene