Cleavage Products of Lycopene Produced by in Vitro Oxidations: Characterization and Mechanisms of Formation

Journal of Agricultural and Food Chemistry

Volumn 51, Issue 25, 2003, Pages 7318-7325

  Caris Veyrat, Catherine ^a   Schmid, Antje ^a,b   Carail, Michel ^a   Böhm, Volker ^b  

^a UMR A 408 INRA University of Avignon   (France)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

Apo carotendial; Apo lycopenal one; Lycopene; Oxidation

Indexed keywords

APO 11 LYCOPENAL; APO 8,6' CAROTENDIAL; APOCAROTENDIAL; APOLYCOPENAL; CAROTENOID; CYTOCHROME P450; LYCOPENE; METALLOPORPHYRIN; OXYGEN; PERMANGANATE POTASSIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBON BOND; CHEMICAL BOND; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE;

CAROTENOIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; METALLOPORPHYRINS; OXIDATION-REDUCTION; OXYGEN; POTASSIUM PERMANGANATE; RUTHENIUM;

EID: 0344198052     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf034735+     Document Type: Article

References (29)

1. Olson, J. A. Carotenoids and human health. Arch. Latin. Nutr. 1999, 49, 7S-11S.
2. Krinsky, N. I. Carotenoids as antioxidants. Nutrition 2001, 17, 815-817.
3. Hughes, D. A. Effects of carotenoids on human immune function. Proc. Nutr. Soc. 1999, 58, 713-718.
4. Stahl, W.; Ale-Agha, N.; Polidori, M. C. Nonantioxidant properties of carotenoids. Biol. Chem. 2002, 383, 553-558.
5. King, T. J.; Khachik, F.; Bortkewicz, H.; Fukushima, S.; Morioka, S.; Bertram, J. S. Metabolites of dietary carotenoids as potential cancer preventive agents. Pure Appl. Chem. 1997, 69, 2135-2140.
6. Khachik, F.; Bertram, J.; Huang, M.-T.; Fahey, J. W.; Talalay, P. Dietary carotenoids and their metabolites as potentially useful chemoprotective agents against cancer. In Antioxidant Food Supplements in Human Health; Academic Press: London, 1999; pp 203-229.
7. Bertram, J. S.; King, T.; Fukishima, L.; Khachik, F.; Sen, C. K.; Sies, H.; Baeuerle, P. A. Enhanced activity of an oxidation product of lycopene found in tomato products and human serum relevant to cancer prevention. In Antioxidant Redox Regulatory Genes; Academic Press: London, 2000; pp 409-424.
8. Agarwal, S.; Rao, A. V. Tomato lycopene and its role in human health and chronic diseases. Can. Med. Assoc. J. 2000, 163, 739-744.
9. Khachik, F.; Carvalho, L.; Bernstein, P. S.; Muir, G. J.; Zhao, D. Y.; Katz, N. B. Chemistry, distribution, and metabolism of tomato carotenoids and their impact on human health. Exp. Biol. Med. 2002, 227, 845-851.
10. Rao, A. V.; Agarwal, S. Role of lycopene as antioxidant carotenoid in the prevention of chronic diseases: A review. Nut. Res. 1999, 19, 305-323.
11. Rao, A. V. R.; Agarwal, S. Role of antioxidant lycopene in cancer and heart disease. J. Am. Coll. Nutr. 2000, 19, 563-569.
12. Hadley, C. W.; Miller, E. C.; Schwartz, S. J.; Clinton, S. K. Tomatoes, lycopene, and prostate cancer: Progress and promise. Exp. Biol. Med. 2002, 227, 869-880.
13. Di Mascio, P.; Kaiser, S.; Sies, H. Lycopene as the most efficient biological carotenoid singlet oxygen quencher. Arch. Biochem. Biophys. 1989, 274, 532-538.
14. Khachik, F.; Spangler, C. J.; Smith, J. C.; Canfield, L.; Steck, A.; Pfander, H. Identification, quantification, and relative concentrations of carotenoids and their serum metabolites in human milk and serum. Anal. Chem. 1997, 69, 1873-1881.
15. Kim, S. J.; Nara, E.; Kobayashi, H.; Terao, J.; Nagao, A. Formation of cleavage products by autoxidation of lycopene. Lipids 2001, 36, 191-199, and references therein.
16. Jorgensen, K.; Skibsted, L. H. Carotenoid scavenging of radicals, effect of carotenoid structure, and oxygen partial pressure on antioxidative activity. Z. Lebensm. Unters. Forsch. 1993, 196, 423-429.
17. Karrer, P.; Jucker, E. Carotenoids; Elsevier: Paris, 1950.
18. Ben-Aziz, A.; Britton, G.; Goodwin, T. W. Carotene epoxides of Lycopersicon esculentum. Phytochemistry 1973, 12, 2759-2764.
19. Ukai, N.; Etoh, H.; Yagi, H.; Ina, K.; Oshima, S.; Ojima, F.; Sakamoto, H.; Ishiguro, Y. Photosensitized oxygenation of lycopene. Biosci. Biotech. Biochem. 1994, 58, 1718-1719.
20. Maerki-Fischer, E.; Uebelhart, P.; Eugster, C. H. 10′ -Apolyco-pin-10′-ol und 10′-apolycopin-10′-saure aus Blueten der Rosenhybride 'Marechal Niel' Helv. Chim. Acta 1987, 70, 1994-2002.
21. Kjoesen, H.; Liaaen-Jensen, S. Major carotenoids of Shepherdia canadensis. Isolation and synthesis of methyl apo-6′-lycopenaoate. Phytochemistry 1969, 8, 483-491.
22. Tsujimo, K.; Aoki, M.; Ohashi, M. Stereoselective photoisomerisation of ψ-retinal. J. Photochem. Photobiol. A 1992, 65, 73-78.
23. Carotenoids Volume 1B: Spectroscopy; Britton, G., Liaaen-Jensen, S., Pfander, H., Eds.; 1995.
24. Karrer, P.; Jaffé, W. Stufenweiser Abbau des Lycopins. Helv. Chim. Acta 1939, 22, 69-71.
25. Yeum, K.-J.; Booth, S. L.; Sadowski, J. A.; Liu, C.; Tang, G.; Krinsky, N. I.; Russel, R. Human plasma carotenoid response to the ingestion of controlled diets high in fruits and vegetables. Am. J. Clin. Nutr. 1996, 64, 594-602
26. Caris-Veyrat, C.; Amiot, M. J.; Ramasseul, R.; Marchon, J. C. Mild oxidative cleavage of beta,beta-carotene by dioxygen induced by a ruthenium porphyrin catalyst: Characterization of products and of some possible intermediates. New J. Chem. 2001, 25, 203-206.
27. Groves, J. T.; Quinn, R. Aerobic epoxidation of olefins with ruthenium porphyrin catalysts. J. Am. Chem. Soc. 1985, 107, 5790-5792.
28. McGrath, D. V.; Grubbs, R. H. The mechanism of aqueous ruthenium(II)-catalyzed olefin isomerization. Organometallics 1994, 13, 224-235.
29. Konovalov, V. V.; Kispert, L. D. AM1, INDO/S and optical studies of carbocations of carotenoid molecules. Acid-induced isomerization. J. Chem. Soc., Perkin Trans. 2 1999, 901-909.