Lycopene oxidation product enhances gap junctional communication.
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.
Aust
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Institut für Biochemie und Molekularbiologie I, Heinrich-Heine-Universität Düsseldorf, Postfach 10 10 07, D-40001 Düsseldorf, Germany.
Ale-Agha
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N
Zhang
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Wollersen
H
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Sies
H
H
Stahl
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W
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
D000975:Antioxidants; D002338:Carotenoids; D003978:Diazomethane; D000077276:Lycopene