Skip to main content

Carotenoid Properties Define Primary Biological Actions and Metabolism Defines Secondary Biological Actions

  • Chapter
Free Radicals, Oxidative Stress, and Antioxidants

Part of the book series: NATO ASI Series ((NSSA,volume 296))

Abstract

The biological properties of carotenoids that can be observed and measured in animals, including humans, in plants, in cells grown in culture, in the microbial worlds, or in the classical “test tube” experiments should all be related to their chemical and physical properties (Britton, 1995; Krinsky, 1993). For example, beta-carotene and lycopene, shown in Figure 1, are both C40H56 hydrocarbons which share many similar properties. They are very hydrophobic, each have 11 conjugated double bonds, although in the case of lycopene, they are all in a linear polyene chain, whereas with β-carotene, only 9 double bonds are in the linear chain, and 2 additional conjugated double bonds are in the rings. As determined by x-ray crystal analysis of beta-carotene, the ring double bonds are slightly out of plane because of the steric hindrance of the methyl group substituents on and near the ring. In addition, because lycopene is an acyclic compound, it has 2 more non-conjugated double bonds at the termini of the molecule. As will be discussed in section 3, these two carotenoids have different biological actions.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Appling, D. R., and Chytil, F., 1981, Evidence for a role of retinoic acid (vitamin A acid) in the maintenance of testosterone production in male rats, Endocrinol. 108: 2120–2122.

    Article  CAS  Google Scholar 

  • Britton, G., 1995, Structure and properties of carotenoids in relation to function, FASEB J. 9: 1551–1558.

    CAS  Google Scholar 

  • Buck, J., Ritter, G., Dannecker, L., Katta, V., Cohen, S. L., Chait, B. T., and Hämmerling, U., 1990, Retinol is essential for growth of activated human B cells, J. Exp. Med. 171: 1613–1624.

    Article  CAS  Google Scholar 

  • Burton, G. W., and Ingold, K. U., 1984, fl-Carotene: An Unusual Type of Lipid Antioxidant, Science 224: 569–573.

    Google Scholar 

  • Chambon, P., 1996, A decade of molecular biology of retinoic acid receptors, FASEB J. 10: 940–953.

    CAS  Google Scholar 

  • Crain, F. D., Lotspeich, F. J., and Krause, R. F., 1967, Biosynthesis of Retinoic Acid by Intestinal Enzymes of the Rat, J. Lipid Res. 8: 249–254.

    CAS  Google Scholar 

  • Giguere, V., Ong, E. S., Segui, P., and Evans, R. M., 1987, Identification of a Receptor for the Morphogen Retinoic Acid, Nature (London) 330: 624–629.

    Article  CAS  Google Scholar 

  • Goodman, D. S., and Huang, H. S., 1965, Biosynthesis of Vitamin A with Rat Intestinal Enzymes, Science 149: 879–880.

    Article  CAS  Google Scholar 

  • Grosch, W., Laskawy, G., and Weber, F., 1976, Formation of Volatile Carbonyl Compounds and Cooxidation of ß-Carotene by Lipoxygenase from Wheat, Potato, Flax, and Beans, J. Agric. Food Chem. 24: 456–459.

    Article  CAS  Google Scholar 

  • Group, E. D. C.-C. S., 1993, Antioxidant Status and Neovascular Age-Related Macular Degeneration, Arch. Ophthalmol. 111: 104–109.

    Article  Google Scholar 

  • Group, T. A.-T. B. C. C. P. S., 1994, The effect of vitamin E and beta carotene on the incidence of lung cancer and other cancers in male smokers, New Engl. J. Med. 330: 1029–1035.

    Article  Google Scholar 

  • Hammond, B. R., Jr., Curran-Celentano, J., Judd, S., Fuld, K., Krinsky, N. I., Wooten, B. R., and Snodderly, D. M., 1996, Sex Differences in Macular Pigment Optical Density: Relation to Plasma Carotenoid Concentrations and Dietary Patterns, Vision Res. in press.

    Google Scholar 

  • Hammond, B. R., Jr., Johnson, E. J., Russell, R. M., Krinsky, N. I., Yeum, K.-J., Edwards, R. B., and Snodderly, D. M., 1997, Dietary modification of human macular pigment density, Invest. Ophthalmol. Vis. Sci. 38: 1795–1801.

    Google Scholar 

  • Handelman, G. J., van Kuijk, F. J. G. M., Chatterjee, A., and Krinsky, N. I., 1991, Characterization of products formed during the autoxidation of I3-carotene, Free Radic. Biol. Med. 10: 427–437.

    Google Scholar 

  • Hebuterne, X., Wang, X.-D., Johnson, E. J., Krinsky, N. I., and Russell, R. M., 1995, Intestinal absorption and metabolism of 9-cis-(3-carotene in vivo: biosynthesis of 9-cis-retinoic acid, J. Lipid Res. 36: 1264–1273.

    CAS  Google Scholar 

  • Hennekens, C. H., Buring, J. E., Manson, J. E., Stampfer, M., Rosner, B., Cook, N. R., Belanger, C., LaMotte, F., Gaziano, J. M., Ridker, P. M., Willett, W., and Peto, R., 1996, Lack of effect of long-term supplementation with beta carotene on the incidence of malignant neoplasms and cardiovascular disease, New Engl. J. Med. 334: 1145–1149.

    Article  CAS  Google Scholar 

  • Jorgensen, K., and Skibsted, L. H., 1993, Carotenoid scavenging of radicals. Effect of carotenoid structure and oxygen partial pressure on antioxidative activity, Z. Lebensm. Unters. Forsch. 196: 423–429.

    Article  CAS  Google Scholar 

  • Krinsky, N. I., 1993, Actions of carotenoids in biological systems, Annu. Rev. Nutr. 13: 561–587.

    Google Scholar 

  • Krinsky, N. I., and Deneke, S. M., 1982, The Interaction of Oxygen and Oxy-Radicals with Carotenoids, JNCI 69: 205–210.

    CAS  Google Scholar 

  • Landrum, J. T., Bone, R. A., and Kilbum, M. D., 1996, The macular pigment: A possible role in protection from age-related macular degeneration, Adv. Pharmacol. 38: 537–556.

    Article  Google Scholar 

  • Mangelsdorf, D. J., Ong, E. S., Dyck, J. A., and Evans, R. M., 1990, Nuclear Receptor that Identifies a Novel Retinoic Acid Response Pathway, Nature (London) 345: 224–229.

    Article  CAS  Google Scholar 

  • Nagao, A., and Olson, J. A., 1994, Enzymatic formation of 9-cis, 13-cis and all-trans retinals from isomers of I3-carotene, FASEB J. 8: 968–973.

    CAS  Google Scholar 

  • Olson, J. A., and Hayaishi, 0., 1965, The Enzymatic Cleavage of 13-Carotene Into Vitamin A by Soluble Enzymes of Rat Liver and Intestine., Proc. Natl. Acad. Sci. USA 54: 1364–1370.

    Google Scholar 

  • Olson, J. A., and Krinsky, N. I., 1995, The colorful fascinating world of the carotenoids, FASEB J. 9: 1547–1550.

    CAS  Google Scholar 

  • Omenn, G. S., Goodman, G. E., Thornquist, M. D., Balmes, J., Cullen, M. R., Glass, A., Keogh, J. P., Meyskens, F. L., Jr., Valanis, B., Williams, J. H., Jr., Barnhart, S., and Hammar, S., 1996, Effects of a combination of beta carotene and vitamin A on lung cancer and cardiovascular disease, New Engl. J. Med. 334: 1150–1155.

    Article  CAS  Google Scholar 

  • Packer, J. E., Mahood, J. S., Mora-Arellano, V. O., Slater, T. F., Willson, R. L., and Wolfenden, B. S., 1981, Free Radicals and Singlet Oxygen Scavengers: Reaction of a Peroxy-radical with 13-Carotene Diphenyl Furan and 1,4-Diazobicyclo(2,2,2)-octane, Biochem. Biophys. Res. Commun. 98: 901–906.

    Article  CAS  Google Scholar 

  • Palozza, P., Calviello, G., and Bartoli, G. M., 1995, Prooxidant activity of (3-carotene under 100% oxygen pressure in rat liver microsomes, Free Radic. Biol. Med. 19: 887–892.

    Article  CAS  Google Scholar 

  • Palozza, P., and Krinsky, N. I., 1992, Antioxidant effects of carotenoids in vitro and in vivo: an overview, Meth. Enzymol. 213: 403–420.

    Article  CAS  Google Scholar 

  • Petkovich, M., Brand, N. J., Krust, A., and Chambon, P., 1987, A Human Retinoic Acid Receptor Which Belongs to the Family of Nuclear Receptors, Nature (London) 330: 444–450.

    Article  CAS  Google Scholar 

  • Peto, R., Doll, R. J., Buckley, J. D., and Sporn, M. B., 1981, Can dietary (3-carotene materially reduce human cancer rates?, Nature (London) 290: 201–208.

    Article  CAS  Google Scholar 

  • Saari, J. C., 1994, Retinoids in photosensitive systems, in: The Retinoids. Biology, Chemistry, and Medicine, (M. B. Sporn, A. B. Roberts, and D. S. Goodman, eds.), vol. pp. 351–385, Raven, New York.

    Google Scholar 

  • Snodderly, D. M., 1995, Evidence for protection against age-related macular degeneration by carotenoids and antioxidant vitamins, Am. J Clin. Nutr. 62 (Suppl):1448S-1461 S.

    Google Scholar 

  • Stratton, S. P., Schaefer, W. H., and Liebler, D. C., 1993, Isolation and Identification of Singlet Oxygen Oxidation Products of I3-Carotene, Chem. Res. Toxicol. 6: 542–547.

    Article  CAS  Google Scholar 

  • Tinkler, J. H., Tavender, S. M., Parker, A. W., McGarvey, D. J., Mulroy, L., and Truscott, T. G., 1996, Investigation of carotenoid radical cations and triplet states by laser flash photolysis and time-resolved resonance Raman spectroscopy: Observation of competitive energy and electron transfer, J. Am. Chem. Soc. 118: 1756–1761.

    Article  CAS  Google Scholar 

  • Wang, X.-D., and Krinsky, N. I., 1997, The bioconversion of 0-carotene into retinoids, in: Subcellular Biochemistry: Fat Soluble Vitamins,(P. J. Quinn, eds.), vol. pp. in press, Plenum, London.

    Google Scholar 

  • Wang, X.-D., Krinsky, N. I., Benotti, P. N., and Russell, R. M., 1994, Biosynthesis of 9-cis-retinoic acid from 9-cis-13-carotene in human intestinal mucosa in vitro, Arch. Biochem. Biophys. 313: 150–155.

    Article  CAS  Google Scholar 

  • Wang, X.-D., Russell, R. M., Liu, C., Stickel, F., Smith, D., and Krinsky, N. I., 1996, 0-Oxidation in rabbit liver in vitro and in the perfused ferret liver contributes to retinoic acid biosynthesis from (3-apo-carotenoic acids, J. Biol. Chem. 271: 26490–26498.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1998 Springer Science+Business Media New York

About this chapter

Cite this chapter

Krinsky, N.I. (1998). Carotenoid Properties Define Primary Biological Actions and Metabolism Defines Secondary Biological Actions. In: Özben, T. (eds) Free Radicals, Oxidative Stress, and Antioxidants. NATO ASI Series, vol 296. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-2907-8_28

Download citation

  • DOI: https://doi.org/10.1007/978-1-4757-2907-8_28

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4419-3292-1

  • Online ISBN: 978-1-4757-2907-8

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics