Oxidative Conversion of Carotenoids to Retinoids and Other Products

Journal of Nutrition

Volumn 134, Issue 1, 2004, Pages

  Nagao, Akihiko ^a  

^a NATIONAL FOOD RESEARCH INSTITUTE   (Japan)

Author keywords

Dioxygenase; Lycopene; Oxidation; Vitamin A; carotene

Indexed keywords

BETA CAROTENE; CAROTENOID; DRUG METABOLITE; LYCOPENE; OXYGENASE; RETINOID;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; BIOAVAILABILITY; CELL STRAIN CACO 2; CELL STRAIN HL 60; CONFERENCE PAPER; ENZYME ACTIVITY; HUMAN; METABOLIC REGULATION; OXIDATION; REACTION ANALYSIS; VITAMIN METABOLISM;

ANIMALIA; SUS SCROFA; VERTEBRATA;

EID: 0347986905     PISSN: 00223166     EISSN: None     Source Type: Journal    
DOI: 10.1093/jn/134.1.237s     Document Type: Conference Paper

References (36)

1. Olson, J. A. & Hayaishi, O. (1965) The enzymatic cleavage of beta-carotene into vitamin A by soluble enzymes of rat liver and intestine. Proc. Natl. Acad. Sci. U.S.A. 54: 1364-1369.
2. Goodman, D. S. & Huang, H. S. (1965) Biosynthesis of vitamin A with rat intestinal enzymes. Science 149: 879-880.
3. Ong, D. E. (1993) Retinoid metabolism during intestinal absorption. J. Nutr. 123: 351-355.
4. Mordi, R. C., Walton, J. C., Burton, G. W., Hughes, L., Ingold, K. U., Lindsay, D. A. & Moffatt, D. J. (1993) Oxidative degradation of β-carotene and β-apo-8′-carotenal. Tetrahedron 49: 911-928.
5. McClure, T. D. & Liebler, D. C. (1995) A rapid method for profiling the products of antioxidant reactions by negative ion chemical ionization mass spectrometry. Chem. Res. Toxicol. 8: 128-135.
6. Stratton, S. P., Schaefer, W. H. & Liebler, D. C. (1993) Isolation and identification of singlet oxygen oxidation products of β-carotene. Chem. Res. Toxicol. 6: 542-547.
7. Nikawa, T., Schulz, W. A., van den Brink, C. E., Hanusch, M., van der Saag, P., Stahl, W. & Sies, H. (1995) Efficacy of all-trans-β-carotene, canthaxanthin, and all-trans-, 9-cis, and 4-oxoretinoic acids in including differentiation of an F9 embryonal carcinoma RARβ-lacZ receptor cell line. Arch. Biochem. Biophy. 316: 665-672.
8. Hu, X., White, K. M., Jacobsen, N. E., Mangelsdorf, D. J. & Canfield, L. M. (1998) Inhibition of growth and cholesterol synthesis in breast cancer cells by oxidation products of β-carotene. J. Nutr. Biochem. 9: 567-574.
9. Wang, X. D., Tang, G. W., Fox, J. G., Krinsky, N. I. & Russell, R. M. (1991) Enzymatic conversion of β-carotene into β-apo-carotenals and retinoids by human, monkey, ferret, and rat tissues. Arch. Biochem. Biophys. 285: 8-16.
10. Napoli, J. L. (1993) Retinoic acid synthesis from β-carotene in vitro. Methods Enzymol. 214: 193-202.
11. Devery, J. & Milborrow, B. V. (1994) Beta-carotene-15, 15′-dioxygenase (EC 1.13.11.21) isolation reaction mechanism and an improved assay procedure. Br. J. Nutr. 72: 397-414.
12. Lakshman, M. R., Mychkovsky, I. & Attlesey, M. (1989) Enzymatic conversion of all-trans-β-carotene to retinal by a cytosolic enzyme from rabbit and rat intestinal mucosa. Proc. Natl. Acad. Sci. U.S.A. 86: 9124-9128.
13. Nagao, A. & Olson, J. A. (1994) Enzymatic formation of 9-cis, 13-cis, and all-trans retinals from isomers of β-carotene. FASEB J. 8: 968-973.
14. Nagao, A., During, A., Hoshino, C., Terao, J. & Olson, J. A. (1996) Stoichiometric conversion of all trans-β-carotene to retinal by pig intestinal extract. Arch. Biochem. Biophys. 328: 57-63.
15. During, A., Nagao, A., Hoshino, C., & Terao, J. (1996) Assay of β-carotene 15,15′-dioxygenase activity by reverse-phase high-pressure liquid chromatography. Anal. Biochem. 241: 199-205.
16. Nagao, A., Maeda, M., Lim, B. P., Kobayashi, H. & Terao, J. (2000) Inhibition of β-carotene-15,15′-dioxygenase activity by dietary flavonoids. J. Nutr. Biochem. 11: 348-355.
17. Furr, H. C. & Clark, R. M. (1997) Intestinal absorption and tissue distribution of carotenoids. J. Nutr. Biochem. 8: 364-377.
18. van het Hof, K. H., West, C. E., Weststrate, J. A. & Hautvast, J.G.A.J. (2000) Dietary factors that affect the bioavailability of carotenoids. J. Nutr. 130: 503-506.
19. Sugawara, T., Kushiro, M., Zhang, H., Nara, E., Ono, H. & Nagao, A. (2002) Lysophosphatidylcholine enhances carotenoid uptake from mixed micelles by Caco-2 human intestinal cells. J. Nutr. 131: 2921-2927.
20. Suruga, K., Suzuki, R., Goda, T. & Takase, S. (1995) Unsaturated fatty acids regulate gene expression of cellular retinol-binding protein, type II in rat jejunum. J. Nutr. 125: 2039-2044.
21. During, A., Nagao, A. & Terao, A. (1998) β-Carotene 15,15′-dioxygenase activity and cellular retinol-binding protein type II level are enhanced by dietary unsaturated triacylglycerols in rat intestines. J. Nutr. 128: 1614-1619.
22. Mochizuki, K., Suruga, K., Kitagawa, M., Takase, S. & Goda, T. (2001) Modulation of the expression of peroxisome proliferator-activated receptor-dependent genes through disproportional expression of two subtypes in the small intestine, Arch. Biochem. Biophys. 389: 41-48.
23. von Lintig, J. & Vogt, K. (2000) Filling the gap in vitamin A research-Molecular identification of an enzyme cleaving beta-carotene to retinal. J. Biol. Chem. 275: 11915-11920.
24. Wyss, A., Wirtz, G., Woggon, W. D., Brugger, R., Wyss, M., Friedlein, A., Bachmann, H. & Hunziker, W. (2000) Cloning and expression of beta, beta-carotene 15,15′-dioxygenase. Biochem. Biophy. Res. Commun. 271: 334-336.
25. Khachik, F., Spangler, C. J., Smith, J. C., Canfield, L. M., Steck, A. & Pfander, H. (1997) Identification, quantification, and relative concentrations of carotenoids and their metabolites in human milk and serum. Anal. Chem. 69: 1873-1881.
26. Bausch, J., Liechti, H., Oesterhelt, G. & Kistler, A. (1999) Isolation and identification of a major urinary canthaxanthin metabolite in rats. Int. Vitam. Nutr. Res. 69: 268-272.
27. Wolz, E., Liechti, H., Notter, B., Oesterhelt, G. & Kistler, A. (1999) Characterization of metabolites of astaxanthin in primary cultures of rat hepatocytes. Drug Metab. Dispos. 27: 456-462.
28. Kim, S. J., Nara, E., Kobayashi, H., Terao, J. & Nagao, A. (2001) Formation of cleavage products by autoxidation of lycopene. Lipids 36: 191-199.
29. Stahl, W., von Laar, J., Martin, H. D., Emmerich, T. & Sies, H. (2000) Stimulation of gap junctional communication: comparison of acyclo-retinoic acid and lycopene. Arch. Biochem. Biophys. 373: 271-274.
30. Duitsman, P. K., Barua, A. B., Becker, B. & Olson, J. A. (1999) Effects of epoxycarotenoids, β-carotene, and retinoic acid on the differentiation and viability of the leukemia cell line NB4 in vitro. Int. J. Vitam. Nutr. Res. 69: 303-308.
31. Gradelet, S., Astorg, P., Leclerc, J. & Siess, M. H. (1996) β-Apo-8′-carotenal, but not β-carotene is a strong inducer of liver CYP1A1 and 1A2 in the rat. Xenobiotica 26: 909-919.
32. Wang, X. D., Liu, C., Bronson, R. T., Smith, D. E., Krinsky, N. I. & Russell, R. M. (1999) Retinoid signaling and activator protein-1 expression in ferrets given beta-carotene supplements and exposed to tobacco smoke. J. Natl. Cancer Inst. 91: 60-66.
33. Salgo, M. G., Cueto, R., Winston, G. W. & Pryor, W. A. (1999) Beta carotene and its oxidation products have different effects on microsome mediated binding of benzo[a]pyrene to DNA. Free Radic. Biol. Med. 26: 162-173.
34. Siems, W. G., Sommerburg, O., Hurst, J. S., van Kuijk, F.J.G.M. (2000) Carotenoid oxidative degradation products inhibit Na+-K+-ATPase. Free Radic. Res. 33: 427-435.
35. Rahman, A. & Parker, R. S. (2001) Carotenoid photodegradation products and human peripheral blood mononuclear cell function. Nutr. Res. 21: 581-596.
36. Nara, E., Hayashi, H., Kotake, M., Miyashita, K. & Nagao, A. (2001) Acyclic carotenoids and their oxidation mixture inhibit the growth of HL-60 human promyelocytic leukemia cells. Nutr. Cancer 39: 273-283.