title: Lycopene oxidation product enhances gap junctional communication.
abstract: Carotenoids as well as their metabolites and oxidation products stimulate gap junctional communication (GJC) between cells, which is thought to be one of the protective mechanisms related to cancer-preventive activities of these compounds. Increased intake of lycopene by consumption of tomatoes or tomato products has been epidemiologically associated with a diminished risk of prostate cancer. Here, we report a stimulatory effect of a lycopene oxidation product on GJC in rat liver epithelial WB-F344 cells. The active compound was obtained by complete in vitro oxidation of lycopene with hydrogen peroxide/osmium tetroxide. For structural analysis high performance liquid chromatography, gas chromatography coupled with mass spectrometry, ultraviolet/visible-, and infrared spectrophotometry were applied. The biologically active oxidation product was identified as 2,7,11-trimethyl-tetradecahexaene-1,14-dial. The present data indicate a potential role of lycopene degradation products in cell signaling enhancing cell-to-cell communication via gap junctions.
authors.affiliation: Institut für Biochemie und Molekularbiologie I, Heinrich-Heine-Universität Düsseldorf, Postfach 10 10 07, D-40001 Düsseldorf, Germany.
authors.forename: O
authors.initials: O
authors.lastname: Aust
authors.forename: N
authors.initials: N
authors.lastname: Ale-Agha
authors.forename: L
authors.initials: L
authors.lastname: Zhang
authors.forename: H
authors.initials: H
authors.lastname: Wollersen
authors.forename: H
authors.initials: H
authors.lastname: Sies
authors.forename: W
authors.initials: W
authors.lastname: Stahl
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology*; D002338:Carotenoids / Q000737:chemistry / Q000494:pharmacology*; D002450:Cell Communication / Q000187:drug effects*; D002851:Chromatography, High Pressure Liquid; D003978:Diazomethane / Q000737:chemistry; D017629:Gap Junctions / Q000187:drug effects*; D000077276:Lycopene; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D051381:Rats; D011916:Rats, Inbred F344; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
chemical_list: D000975:Antioxidants; D002338:Carotenoids; D003978:Diazomethane; D000077276:Lycopene