Formation Of Apocarotenals And Epoxycarotenoids From β-carotene By Chemical Reactions And By Autoxidation In Model Systems And Processed Foods

dc.creatorRodriguez E.B.
dc.creatorRodriguez-Amaya D.B.
dc.date2007
dc.date2015-06-30T18:47:10Z
dc.date2015-11-26T14:35:39Z
dc.date2015-06-30T18:47:10Z
dc.date2015-11-26T14:35:39Z
dc.date.accessioned2018-03-28T21:39:04Z
dc.date.available2018-03-28T21:39:04Z
dc.identifier
dc.identifierFood Chemistry. , v. 101, n. 2, p. 563 - 572, 2007.
dc.identifier3088146
dc.identifier10.1016/j.foodchem.2006.02.015
dc.identifierhttp://www.scopus.com/inward/record.url?eid=2-s2.0-33748293152&partnerID=40&md5=91cae590093b66aa94167ebc18fe590c
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/104770
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/104770
dc.identifier2-s2.0-33748293152
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1248434
dc.descriptionIt is generally accepted that oxidation of carotenoids begins with epoxidation and cleavage to apocarotenals. However, systematic studies to demonstrate occurrence of these reactions are lacking. In this study, the products formed by epoxidation with m-chloroperbenzoic acid (MCPBA), oxidative cleavage with KMnO4 and autoxidation in model systems, in the presence and absence of light, at ambient condition were identified. The presence of oxidation products was also verified in processed products. β-carotene-5,6-epoxide, β-carotene-5,8-epoxide, β-carotene-5,6,5′,6′-diepoxide, β-carotene-5,6,5′,8′-diepoxide and β-carotene 5,8,5′,8′-diepoxide were formed by the reaction of β-carotene with MCPBA. The oxidation products with KMnO4 were identified as β-apo-8′-carotenal, β-apo-10′-carotenal, β-apo-12′-carotenal, β-apo-14′-carotenal and β-apo-15-carotenal, along with semi-β-carotenone and monohydroxy-β-carotene-5,8-epoxide. Except for β-carotene 5,6,5′,6′-diepoxide, these products were detected in the model systems. Some of these products were also found in mango juice, acerola juice and dried apricot. Increased Z-isomerization was also observed and Z-isomers of the oxidation products were detected. © 2006 Elsevier Ltd. All rights reserved.
dc.description101
dc.description2
dc.description563
dc.description572
dc.descriptionBritton, G., Carotenoids (1991) Methods in Plant Biochemistry, 7, pp. 473-518
dc.descriptionBritton, G., UV/visible spectroscopy (1995) Carotenoids vol. 1B: Spectroscopy, pp. 13-63. , Britton G., Liaaen-Jensen S., and Pfander H. (Eds), Birkhäuser Verlag, Basel
dc.descriptionDavies, B.H., Carotenoids (1976) Chemistry and biochemistry of plant pigments, pp. 38-165. , Goodwin T.W. (Ed), Academic Press, London
dc.descriptionEl-Tinay, A.H., Chichester, C.O., Oxidation of β-carotene. Site of initial attack (1970) Journal of Organic Chemistry, 35, pp. 2290-2293
dc.descriptionEnzell, C.R., Back, S., (1995) Carotenoids vol. 1B: Spectroscopy, pp. 261-320. , Britton G., Liaaen-Jensen S., and Pfander H. (Eds), Birkhäuser Verlag, Basel
dc.descriptionHandelman, G.J., van Kuijk, F.J.G.M., Chatterjee, A., Krinsky, N.I., Characterization of products formed during the autoxidation of β-carotene (1991) Free Radical Biology and Medicine, 10, pp. 427-437
dc.descriptionHenry, L.K., Puspitasari-Nienabe, N.L., Jarén-Galán, M., van Breemen, R.B., Castignani, G.L., Schwartz, S.J., Effects of ozone and oxygen on the degradation of carotenoids in an aqueous system (2000) Journal of Agricultural and Food Chemistry, 48, pp. 5008-5013
dc.descriptionKanasawud, P., Crouzet, J.C., Mechanism of formation of volatile compounds by thermal degradation of carotenoids in aqueous medium. 1. β-Carotene degradation (1990) Journal of Agricultural and Food Chemistry, 38, pp. 237-243
dc.descriptionKing, T.J., Khachik, F., Bortkiewicz, H., Fukushima, L.H., Morioka, S., Bertram, J.S., Metabolites of dietary carotenoids as potential cancer preventive agents (1997) Pure and Applied Chemistry, 69, pp. 2135-2140
dc.descriptionMarty, C., Berset, C., Degradation of trans-β-carotene during heating in sealed glass tubes and extrusion cooking (1986) Journal of Food Science, 51, pp. 698-702
dc.descriptionMarty, C., Berset, C., Degradation products of trans-β-carotene produced during extrusion cooking (1988) Journal of Food Science, 53, pp. 1880-1886
dc.descriptionMarty, C., Berset, C., Factors affecting the thermal degradation of all-trans-β-carotene (1990) Journal of Agricultural and Food Chemistry, 38, pp. 1063-1067
dc.descriptionMercadante, A.Z., Steck, A., Pfander, H., Carotenoids from guava (Psidium guajava L.): isolation and structure elucidation (1999) Journal of Agricultural and Food Chemistry, 47, pp. 145-151
dc.descriptionOnyewu, P.N., Ho, C.T., Daun, H., Characterization of β-carotene thermal degradation products in a model food system (1986) Journal of the American Oil Chemists' Society, 63, pp. 1437-1441
dc.descriptionOuyang, J.M., Daun, H., Chang, S.S., Ho, C.T., Formation of carbonyl compounds from β-carotene during palm oil deodorization (1980) Journal of Food Science, 45, pp. 1214-1217
dc.descriptionRodriguez-Amaya, D.B., (1999) A guide to carotenoid analysis in foods, , ILSI Press, Washington DC
dc.descriptionSchiedt, K., Liaaen-Jensen, S., Isolation and analysis (1995) Carotenoids vol. 1A: Isolation and analysis, pp. 81-108. , Britton G., Liaaen-Jensen S., and Pfander H. (Eds), Birkhäuser Verlag, Basel
dc.descriptionSiems, E., Sommeburg, O., Schild, L., Augustin, W., Langhans, C.-D., Wiswedel, I., β-Carotene cleavage products induce oxidative stress in vitro by impairing mitochondrial respiration (2002) The FASEB Journal, 16, pp. 1289-1291
dc.languageen
dc.publisher
dc.relationFood Chemistry
dc.rightsfechado
dc.sourceScopus
dc.titleFormation Of Apocarotenals And Epoxycarotenoids From β-carotene By Chemical Reactions And By Autoxidation In Model Systems And Processed Foods
dc.typeArtículos de revistas


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