Abstract
The thermal and oxidative degradation of carotenoids was studied in an oil model system to determine their relative stabilities and the major β-carotene isomers formed during the reaction. All-trans β-carotene, 9-cis β-carotene, lycopene, and lutein were heated in safflower seed oil at 75, 85, and 95°C for 24, 12, and 5 h, respectively. The major isomers formed during heating of β-carotene were 13-cis, 9-cis, and an unidentified cis isomer. The degradation kinetics for the carotenoids followed a first-order kinetic model. The rates of degradation were as follows: lycopene>all-trans β-carotene≈9-cis β-carotene>lutein. The values for the thermodynamic parameters indicate that a kinetic compensation effect exists between all of the carotenoids. These data suggest that lycopene was most susceptible to degradation and lutein had the greatest stability in the model system of the carotenoids tested. Furthermore, there was no significant difference in the rates of degradation for 9-cis and all-trans β-carotene under the experimental conditions.
Similar content being viewed by others
References
Bendich, A. Recent Advances in Clinical Research Involving Carotenoids, Pure Appl. Chem. 66:1017–1024 (1994).
Gey, K., Prospects for the Prevention of Free Radical Disease, Regarding Cancer and Cardiovascular Disease, Br. Med. Bull. 49:679–699 (1993).
Govannucci, E., A. Ascherio, E.B. Rimm, M.J. Stampfer, G.A. Colditz, and W.C. Willett, Intake of Carotenoids and Retinol in Relation to Risk of Prostate Cancer, J. Natl. Cancer Inst. 87:1767–1776 (1995).
Kennedy, T.A., and D.C. Liebler, Peroxyl Radical Oxidation of β-Carotene: Formation of β-Carotene Epoxides, Chem. Res. Toxicol. 4:290–295 (1991).
Warner, K., and E. Frankel, Effects of β-Carotene on Light Stability of Soybean Oil, J. Am. Oil. Chem. Soc. 64:213–218 (1987).
Kiritsakis, A., and L.R. Dugan, Studies in Photooxidation of Olive Oil, Ibid.:892–896 (1985).
Foote, C., and R. Denny, Chemistry of Singlet Oxygen. VII. Quenching by β-Carotene, J. Am. Chem. Soc. 90:6233 (1968).
Baloch, A.K., K.A. Buckle, and R.A. Edwards, Stability of β-Carotene in Model Systems Containing Sulphite, J. Food Technol. 12:309–316 (1977).
Pesek, C.A. and J.J. Warthesen, Characterization of the Photodegradation of β-Carotene in Aqueous Model Systems, J. Food Sci. 53:1517–1520 (1988).
Minguez-Mosquera, M.I., and M. Jaren-Galan, Kinetics of the Decolouring of Carotenoid Pigments, J. Sci. Food Agric. 67:153–161 (1995).
Stefanovich, A.F., and M. Karel, Kinetics of Beta-Carotene Degradation at Temperatures Typical of Air Drying of Foods, J. Food Proc. Pres. 6:227–242 (1982).
Chou, H., and W. Breene, Oxidative Decoloration of β-Carotene in Low-Moisture Model Systems, J. Food Sci. 37:66–68 (1972).
Haralampu, S.G., and M. Karel, Kinetic Models for Moisture Dependence of Ascorbic Acid and β-Carotene Degradation in Dehydrated Sweet Potato, Ibid.:1872–1873 (1983).
Ramakrishnan, T.V., and F.J. Francis, Stability of Carotenoids in Model Aqueous Systems, J. Food Qual. 2:177–189 (1979).
El-Tinay, A.H., and C.O. Chichester, Oxidation of β-Carotene. Site of Initial Attack, J. Org. Chem. 35:2290–2293 (1970).
Goldman, M., B. Horev, and I. Saguy, Decolorization of β-Carotene in Model Systems Simulating Dehydrated Foods. Mechanism and Kinetic Principles, J. Food Sci. 48:751–754 (1983).
Philip, T., and F.J. Francis, Oxidation of Capsanthin, Ibid.:96–97 (1971).
Mordi, R.C., J.C. Walton, G.W. Burton, L. Hughes, K.U. Ingold, and D.A. Lindsay, Exploratory Study of β-Carotene Autoxidation, Tetrahedron Lett. 32:4203–4206 (1991).
O’Neil, C.A. and S.J. Schwartz, Chromatographic Analysis of cis/trans Carotenoid Isomers, J. Chromatogr. 624:235–252 (1992).
Emenhiser, C., G. Englert, L.C. Sander, B. Ludwig, and S.J. Schwartz, Isolation and Structural Elucidation of the Predominant Geometrical Isomers of α-Carotene, J. Chromatogr. A 719:333–343 (1996).
Sander, L.C., K.E. Sharpless, N.E. Craft, and S.A. Wise, Development of Engineered Stationary Phases for the Separation of Carotenoid Isomer, Anal. Chem. 66:1667–1674 (1994).
Rhim, J.W., V.A. Jones, and K.R. Swartzel, Appearance of a Kinetic Compensation Effect in the Acid-Catalyzed Hydrolysis of Disaccharides, J. Food Sci. 54:222–223 (1989).
Pysiak, J., and B. Sabalski, Compensation Effect and Isokinetic Temperature in Thermal Dissociation Reactions of the Type Asolid = Bsolid + Cgas. Interpretation of the Arrhenius Equation as a Projection Correlation, J. Thermal Anal. 17:287 (1979).
Ray, A.A., Statistical Analysis System User’s Guide: Statistics, Statistical Analysis System Institute, Cary, 1990.
Stahl, W., and H. Sies, Physical Quenching of Singlet Oxygen and cis-trans Isomerization of Carotenoids, Ann. N.Y. Acad. Sci. 691:10–19 (1993).
Levin, G., and S. Mokady, Antioxidant Activity of 9-cis Compared to All-trans β-Carotene In Vitro, Free Radicals Biol. Med. 17:77–82 (1994).
Jimenez, C., and U. Pick, Differential Reactivity of β-Carotene Isomers from Dunaliella bardawil Toward Oxygen Radicals, Plant Physiol. 101:385–390 (1993).
DiMascio, P., S. Kaiser, and H. Sies, Lycopene as the Most Efficient Biological Carotenoid Singlet Oxygen Quencher, Arch. Biochem. Biophys. 274:532–538 (1989).
Canjura, F.L., S.J. Schwartz, and R.V. Nunes, Degradation Kinetics of Chlorophylls and Chlorophyllides, J. Food Sci. 56:1639–1643 (1991).
Rhim, J.W., V.A. Jones, and K.R. Swartzel, Kinetic Compensation Effect in the Heat Denaturation of Whey Protein, Ibid.:589–592 (1990).
Lessin, W.J., G.L. Catignani, and S.J. Schwartz, Quantification of cis-trans Isomers of Provitamin A Carotenoids in Fresh and Processed Fruits and Vegetables, J. Agric. Food Chem. 45:3728–3732 (1997).
Emenhiser, C., L.C. Sanders, and S.J. Schwartz, Capability of a Polymeric C30 Stationary Phase to Resolve cis-trans Carotenoid Isomers in a Reversed Phase Liquid Chromatography, J. Chromatogr. A 707:205–216 (1995).
Pettersson, A., and L. Jonsson, Separation of cis-trans Isomers of Alpha- and Beta-Carotene by Adsorption HPLC and Identification with Diode Array Detection, J. Micronutr. Anal. 8:23–41 (1990).
O’Neil, C.A., S.J. Schwartz, and G.L. Catignani, Comparison of Liquid Chromatographic Methods for Determination of cis-trans Isomers of β-Carotene, Off. Anal. Chem. 74:36–42 (1991).
Chandler, L.A., and S.J. Schwartz, Isomerization and Losses of trans-β-Carotene in Sweet Potatoes as Affected by Processing Treatments, J. Agric. Food Chem. 36:129–133 (1988).
Chen, B.H., T.M. Chen, and J.T. Chien, Kinetic Model for Studying the Isomerization of α- and β-Carotene During Heating and Illumination, Ibid.:2391–2397 (1994).
Author information
Authors and Affiliations
Corresponding author
About this article
Cite this article
Henry, L.K., Catignani, G.L. & Schwartz, S.J. Oxidative degradation kinetics of lycopene, lutein, and 9-cis and all-trans β-carotene. J Amer Oil Chem Soc 75, 823–829 (1998). https://doi.org/10.1007/s11746-998-0232-3
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s11746-998-0232-3