The degradation of (all-E)-β-carotene by cigarette smoke

The effects of cigarette smoke in promoting the degradation of (all-E)-β-carotene have been studied, but some conflicting results promoted a further study. β-Carotene was solubilized in hexane and challenged with filtered cigarette smoke both at room temperature and at −20°C. The products arising from smoke-induced oxidation were assessed using a combination of HLPC-DAD, LC-MS and GC-MS. At room temperature the degradation of β-carotene was very rapid, with only a few products being detected using HPLC-DAD. A range of volatile products including β-ionone, β-cyclocitral and 5,6-epoxy-β-ionone were detected using GC-MS. In contrast, when the reaction was slowed (by reducing the reaction temperature), a much wider range of products could be detected by HPLC-DAD, including 4-nitro-β-carotene and several of its geometric isomers. These degradation products suggest that the C4 position on the β-carotene end-group plays a key role in initiating free radical attack.

[1]  Brian L. Lindshield,et al.  Lycopenoids: are lycopene metabolites bioactive? , 2007, Archives of biochemistry and biophysics.

[2]  Y. Yamaguchi,et al.  Oxidants in the gas phase of cigarette smoke pass through the lung alveolar wall and raise systemic oxidative stress. , 2007, Journal of pharmacological sciences.

[3]  R. Russell,et al.  β-Carotene and β-Apo-14′-Carotenoic Acid Prevent the Reduction of Retinoic Acid Receptor β in Benzo[a]pyrene-Treated Normal Human Bronchial Epithelial Cells , 2004 .

[4]  O. Sommerburg,et al.  Cytotoxic and genotoxic effects of b-carotene breakdown products on primary rat hepatocytes , 2004 .

[5]  R. Russell,et al.  Beta-carotene and beta-apo-14'-carotenoic acid prevent the reduction of retinoic acid receptor beta in benzo[a]pyrene-treated normal human bronchial epithelial cells. , 2004, The Journal of nutrition.

[6]  O. Sommerburg,et al.  Cytotoxic and genotoxic effects of β-carotene breakdown products on primary rat hepatocytes , 2003 .

[7]  C. Salerno,et al.  Beta-carotene cleavage products after oxidation mediated by hypochlorous acid--a model for neutrophil-derived degradation. , 2003, Free radical biology & medicine.

[8]  V. Böhm,et al.  Cleavage products of lycopene produced by in vitro oxidations: characterization and mechanisms of formation. , 2003, Journal of agricultural and food chemistry.

[9]  A. Napolitano,et al.  Nitrite-induced nitration pathways of retinoic acid, 5,6-epoxyretinoic acid, and their esters under mildly acidic conditions: toward a reappraisal of retinoids as scavengers of reactive nitrogen species. , 2003, Chemical research in toxicology.

[10]  W. Stahl,et al.  Divergent Optimum Levels of Lycopene, β-Carotene and Lutein Protecting Against UVB Irradiation in Human Fibroblasts¶ , 2002 .

[11]  D. Liebler,et al.  Interactions of β-carotene and cigarette smoke in human bronchial epithelial cells , 2001 .

[12]  Abdur Rahman,et al.  Beta-carotene degradation by cigarette smoke in hexane solution in vitro , 2001 .

[13]  D. Liebler,et al.  Reactions of beta-carotene with cigarette smoke oxidants. Identification of carotenoid oxidation products and evaluation of the prooxidant/antioxidant effect. , 1999, Chemical research in toxicology.

[14]  A. Young,et al.  β‐Carotene enhances hydrogen peroxide‐induced DNA damage in human hepatocellular HepG2 Cells , 1999, FEBS letters.

[15]  A. Young,et al.  Lycopene and beta-carotene protect against oxidative damage in HT29 cells at low concentrations but rapidly lose this capacity at higher doses. , 1999, Free radical research.

[16]  N. Krinsky The Antioxidant and Biological Properties of the Carotenoids a , 1998, Annals of the New York Academy of Sciences.

[17]  G. Britton,et al.  Oxidation of carotenoids by free radicals: relationship between structure and reactivity. , 1997, Biochimica et biophysica acta.

[18]  M R Cullen,et al.  Risk factors for lung cancer and for intervention effects in CARET, the Beta-Carotene and Retinol Efficacy Trial. , 1996, Journal of the National Cancer Institute.

[19]  G. Britton,et al.  Structure and properties of carotenoids in relation to function , 1995, FASEB journal : official publication of the Federation of American Societies for Experimental Biology.

[20]  D. Albanes,et al.  The effect of vitamin E and beta carotene on the incidence of lung cancer and other cancers in male smokers. , 1994, The New England journal of medicine.

[21]  W. Pryor,et al.  Oxidants in Cigarette Smoke Radicals, Hydrogen Peroxide, Peroxynitrate, and Peroxynitrite a , 1993, Annals of the New York Academy of Sciences.

[22]  K. Tsukida [26] Separation of isomers of cis-β-carotenes , 1992 .

[23]  J. Bertram,et al.  Carotenoids enhance gap junctional communication and inhibit lipid peroxidation in C3H/10T1/2 cells: relationship to their cancer chemopreventive action. , 1991, Carcinogenesis.

[24]  Y. Koyama,et al.  Separation and determination of cis/trans-β-carotenes by high-performance liquid chromatography , 1982 .

[25]  G. Karmakar,et al.  On Some Dehydrogenation Products of α-Carotene, β-Carotene and Cryptoxanthin , 1955 .

[26]  L. Zechmeister,et al.  Action of N-Bromosuccinimide on β-Carotene , 1953 .