350 rub
Journal №9 for 2013 г.
Article in number:
The structure and biological functions of carotenoids (review)
Keywords: carotenoids structure biological activity biological functions
Authors:
S. Pechinsky - Ph.D. (Pharm.), Pyatigorsk Medical and Pharmaceutical Institute - a branch of Volgograd state medical university. E-mail: hplc@yandex.ru A. Kuregyan - Ph.D. (Pharm.), Pyatigorsk Medical and Pharmaceutical Institute - a branch of Volgograd state medical university. E-mail: Kooreguan@mail.ru
Abstract:
The article is focused on the problems of interrelation of the structure and biological effect of one of the most wide spread classes of natural biologically active compounds - carotenoids. The number of carotenoids revealed increasing annually; many reports are published on their functions. Nowadays the scientific literature gives no definite answer to the problems concerning the conformity between the structure and biological activity of carotenoids. From this point of view it is important to reveal the correlation of the е «structure - activity» of this class of compounds, as the influence of this factor is the main in displaying the biological effect. This review touches upon the following aspects: nomenclature of carotenoids, the impact of isomery on biological activity of carotenoids, interaction of carotenoids with light, photo protective and antioxidant activity of carotenoids in the cell membrane, and biological function of oxidation products of some carotenoids. The research works, summarized in this review, show that some biological functions of carotenoids are not studied enough. It is primarily explained by the wide variety of structures, and characteristic peculiarities of this class of substance. Carotenoids are the inseparable components for the normal functioning of the organism along with other natural compounds, such as proteins, fats, carbohydrates and vitamins. Analyses of several types of carotenoids activity, discussed in the article, proved the importance of further research of this class of compounds, but from the point of view of their influence on the immune system. Besides, empirical research on revealing and stabilizing of some carotenoids isomers allows both increasing activity of these compounds and considering this activity in the process of creation of medical products based on these compounds.
Pages: 4-14
References

  1. Britton G. Bioximiya prirodny'x pigmentov // M.: Mir. 1986. 422 s.
  2. Eugster C.H. Carotenoid structures, old and new problems // Pure. Appl. Chem. 1985. V. 57. P. 639 - 647.
  3. Britton G., Liaaen-Jensen S., Pfander H., et al. Carotenoid Handbook. Compiled by A. Mercadante, E.S. Egeland. Basel: Birkhäuser. 2003. 671 p.
  4. Nomenclature of carotenoids. IUPAC Commission of the Nomenclature of Organic Chemistry and the IUPAC-IUB Commission on Biochemical Nomenclature // Pure. Appl. Chem. 1975. P 407 - 431.
  5. Khan N., Loeber D.E., Toube T.P., Weedon B.C. Carotenoids and related compounds. Part XXX. Stereochemistry and synthesis of phytoene // J. Chem. Soc. Perkin 1975. V. 15. R. 1457 - 1464.
  6. Foss P., Storebakken T., Schiedt K., et al. Carotenoids in diets for salmonids. 1. Pigmentation of rainbow trout with the individual optical isomers of astaxanthin in comparison with canthaxanthin // Aquaculture 1984. P. 213 - 226.
  7. Liaaen-Jensen S. Stereochemical aspects of carotenoids // Pure. Appl. Chem. 1997. V. 69. P. 2027 - 2039.
  8. Werman M.J., Mokady S., Ben-Amotz A. Bioavailability of the isomer mixture of phytoene and phytofluene-rich alga Dunaliella bardawil in rat plasma and tissues // J. Nutr. Biochem. 2002. V. 13. P. 585 - 591.
  9. Stahl W., Schwarz W., von Laar J., Sies H. All-trans beta-carotene preferentially accumulates in human chylomicrons and very low density lipoproteins compared with the 9-cis geometrical isomer // J. Nutr. 1995. V. 125. P. 2128 - 2133.
  10. Kopsell D.A. Chapter 40 - Carotenoids in Vegetables: Biosynthesis, Occurrence, Impacts on Human Health, and Potential for Manipulation // Bioactive Foods in Promoting Health, Jan. 2010. R. 645 - 662.
  11. Lessin W., Catigani G., Schwartz S.J. Quantification of cis-trans isomers of provitamin A carotenoids in fresh and processed fruits and vegetables // J. Agric. Food. Chem. 1997. V. 45. P. 3728 - 3732.
  12. Martin H.D., Ruck C., Schmidt M. et al. Chemistry of carotenoid oxidation and free radical reactions // Pure. Appl. Chem. 1999. V. 71. P. 2253 - 2262.
  13. Schwartz J.L. In vitro biological methods for determination of carotenoid activity // Meth. Enzymol. 1993. V. 214. P. 226 - 256.
  14. Schmitz H.H., Emenhiser C., Schwartz S.J. HPLC separation of geometric carotene isomers using a calcium hydroxide stationary phase // J. Agric. Food. Chem. 1995. V. 43. P. 1212 - 1218.
  15. Saleh M.H., Tan B. Separation and identification of cis/trans carotenoid isomer // J. Agric. Food. Chem. 1991. V. 39. P. 1438 - 1443.
  16. Edge R., Truscott T.G. Carotenoids: free radical interactions // The Spectrum. 2000. V. 13. P. 12 - 20.
  17. Liaaen-Jensen S. Stereochemical aspects of carotenoids // Pure. Appl. Chem. 1997. V. 69. P. 2027 - 2039.
  18. Sliwka H-R., Liaaen-Jensen S. Partial syntheses of diastereomeric carotenols // Acta. Chem. Scand. 1987. V.41. P. 518 - 525.
  19. Refvem T., Strand A., Kjeldstad B., et al. Stereoisomerization of allenic carotenoids-kinetic, thermodynamic and mechanistic aspects // Acta. Chem. Scand. 1999. V. 53. P. 118 ? 123.
  20. Haugan J.A., Englert G., Glinz E., Liaaen-Jensen S. Structural Assignments of geometrical isomers of fucoxanthin // Acta. Chem. Scand. 1992. V. 46. P. 389 - 395.
  21. Strand A., Liaaen-Jensen S. Application of diphenyldiselenide as a new catalyst for photochemical stereoisomerization of carotenoids // Acta. Chem. Scand. 1998. V. 52. P. 1263 - 1269.
  22. Fiksdahl A., Mortensen J.T., Liaaen-Jensen S. High-pressure liquid chromatography of carotenoids // J. Chromatogr. 1978. V. 157. P. 111 - 117.
  23. Katrangi N., Kaplan L.A., Stein E.A. Separation and quantitation of serum beta carotene and other carotenoids by high performance liquid chromatography // J. Lipid. Res. 1984. V. 25. P. 400 - 406.
  24. Schmitz H.H., Emenhiser C., Schwartz S.J. HPLC separation of geometric carotene isomers using a calcium hydroxide stationary phase // J. Agric. Food. Chem. 1995. V. 43. P. 1212 - 1218.
  25. Lyan B., Azaıs-Braesco V., Cardinault N. et al. Simple method for clinical determination of 13 carotenoids in human plasma using an isocratic high-performance liquid chromatographic method // J. Chromatogr. 2001. V. 751. P. 297 - 303.
  26. Bieri J.G., Brown E.D., Smith J.C. Determination of individual carotenoids in human plasma by high performance liquid chromatography // J. Liq. Chromatog. 1985. V. 8. P. 473 - 484.
  27. Bui M.H. Simple determination of retinol, a-tocopherol and carotenoids (lutein, alltrans- lycopene, α- and β-carotenes) in human plasma by isocratic liquid chromatography // J. Chromatogr. 1994. V. 654. P. 129 - 133.
  28. Clinton S.K., Emenhiser C., Schwartz S.J., et al. Cis-trans lycopene isomers, carotenoids, and retinol in the human prostate // Cancer Epidemiol. Biomark. Prev. 1996. V. 5. P. 823 - 833.
  29. Osterlie M., Bjerkeng B., Liaaen-Jensen S. Plasma appearance and distribution of astaxanthin E/Z and R/S isomers in plasma lipoproteins of men after single dose administration of astaxanthin // J. Nutr. Biochem. 2000. V. 11. P. 482 - 490.
  30. Van Lieshout M., West C.E., Van Breemen R.B. Isotopic tracer techniques for studying the bioavailability and bioefficacy of dietary carotenoids, particularly betacarotene, in humans: a review // Am. J. Clin. Nutr. 2003. V. 77. P. 12 - 28.
  31. Britton G. Structure and properties of carotenoids in relation to function // FASEB J. 1995. V. 9. P. 1551? 1558.
  32. Frank H.A. Spectroscopic studies of the low-lying singlet excited electronic states and photochemical properties of carotenoids // Archives of Biochemistry and Biophysics. 2001. V. 385. P. 53 - 60.
  33. Ruban A.V., Horton P., Young A.J. Aggregation of higher plant xanthophylls: differences in absorption spectra and in dependency on solvent polarity // J. Photobiol. Photobiochem. 1993. V. 21. P. 229 - 234.
  34. Zechmeister L., Polgar A. Cis-trans isomerization and cis-peak effect in the alpha carotene set and in someother stereoisomeric sets // J. Am. Chem. Soc. 1944. V. 66. P. 137 ? 144.
  35. Frank H.A.? Desamero R.Z.B. - Chynwat V. Spectroscopic properties of spheroidene analogs having different extents of π-electron conjugation // J. Phys. Chem. A. 1997. V. 101. P. 149 - 157.
  36. Bennedsen M., Wang X., Willen R. et al. Treatment of H. pylori infected mice with antioxidant astaxanthin reduces gastric inflammation, bacterial load and modulates cytokine release by splenocytes // Immunol. Lett. 1999. V. 70. P. 185 - 189.
  37. Renstrom B., Ronneberg H., Borch G., Liaaen-Jensen S. Animal carotenoids 28. Further studies on the carotenoproteins crustacyanin and ovoverdin // Comp. Biochem. Physiol. 1982. V. 71. P. 249 - 252.
  38. Cosgrove S.A., Guite M.A., Burnell T.B., Christensen R.L. Electronic relaxation in long polyenes // J. Phys. Chem. 1990. V. 94.P. 8118 - 8124.
  39. Olson J.A. Benefits and liabilities of vitamin A and carotenoids // J. Nutr. 1996. V. 126. P. 1208 ? 1212.
  40. Young A.J., Lowe G.M. Antioxidant and prooxidant properties of carotenoids // Arch. Biochem. Biophys. 2001. V. 385. P. 20 - 27.
  41. Palozza P. Prooxidant actions of carotenoids in biological systems // Nutr. Rev. 1998. V. 56. P. 257 - 265.
  42. Schwartz J.L. The dual roles of nutrients as antioxidants and prooxidants: their effects on tumor cell growth // J. Nutr. 1996. V. 126. P. 1221 - 1227.
  43. Rice-Evans C.A., Sampson J., Bramley P.M., Holloway D.E. Why do we expect carotenoids to be antioxidants in vivo - // Free Radic. Res. 1997. V. 26. P. 381 - 398.
  44. Young A.J., Lowe G.M. Antioxidant and prooxidant properties of carotenoids // Arch. Biochem. Biophys. 2001. V. 385. P. 20 - 27.
  45. Mathews-Roth M.M., Pathak M.A., Fitzpatrick T.B., et al. Beta-carotene as a photoprotective agent in erythropoietic protoporphyria // Trans Assoc. Am. Phys. 1970. V. 83. P. 176 - 184.
  46. Frank H.A., Young A.J., Britton G., Cogdell R.J. The Photochemistry of Carotenoids // London: Kluwer Academic. 1999. 385 p.
  47. Mathews-Roth M.M. Carotenoids in erythropoietic protoporphyria and other photosensitivity diseases // Ann. NY. Acad. Sci. 1993. V. 691. P. 127-138.
  48. Liu G. Y., Essex A., Buchanan J.T., et al. Staphylococcus aureus golden pigment impairs neutrophil killing and promotes virulence through its antioxidant activity // J. Exp. Med. 2005. P. 209 - 215.
  49. Pelz K.P., Wieland K., Putzbach P. et al. Structure and Biosynthesis of Staphyloxanthin from Staphylococcus aureus // J. Biol. Chem. 2005. V. 280. P. 32493 - 32498.
  50. Burton G.W., Ingold K.U. β-Carotene: an unusual type of lipid antioxidant // Science. 1984. V. 224.P. 569 - 573.
  51. Gruszeckia W.I., Strzałka K. Carotenoids as modulators of lipid membrane physical properties // Biochimica et Biophysica Acta. 2005. V. 1740. P. 108 - 115.
  52. Gruszecki W.I., Sielewiesiuk J. Orientation of xanthophylls in phosphatidylcholine multibilayers // Biochim. Biophys. Acta. 1990. V. 1023. P. 405 - 412.
  53. Van de Ven M., Kattenberg M., Van Ginkel G., Levine Y.K. Study of the orientational ordering of carotenoids in lipid bilayers by resonance Raman spectroscopy // Biophys. J. 1984. V. 45. P. 1203 - 1210.
  54. Sujak A., Okulski W., Gruszecki W.I. Organization of xanthophyll pigments lutein and zeaxanthin in lipid membranes formed with dipalmitoylphosphatidylcholine // Biochim. Biophys. Acta. 2000. V. 1509. P. 255 - 263.
  55. Varkonyi Z., Masamoto K., Debreczeny M., et al. Low-temperature-induced accumulation of xanthophylls and its structural consequences in the photosynthetic membranes of the cyanobacterium Cylindrospermopsis raciborski: an FTIR spectroscopic study // Proc. Natl. Acad. Sci. USA. 2002. V. 99. P. 2410 - 2415.
  56. Socaciu C., Lausch C., Diehl H.A. Carotenoids in DPPC vesicles: membrane dynamics // Spectrochim. Acta. A. 1999. V. 55. P. 2289 - 2297.
  57. Hara M., Yuan H., Yang Q., et al. Stabilization of liposomal membranes by thermozeaxanthins: carotenoid-glucoside esters // Biochim. Biophys. Acta. 1999. V. 1461. P. 147 - 154.
  58. Okulski W., Sujak A., Gruszecki W.I. Dipalmitoylphosphatidylcholine membranes modified with zeaxanthin: numeric study of membrane organization // Biochim. Biophys. Acta. 2000. V. 1509. P. 216 - 228.
  59. Milon A., Wolff G., Ourisson G., Nakatani Y. Organization of carotenoidphospholipid bilayer systems. Incorporation of zeaxanthin, astaxanthin, and their C50 homologues into dimyristoylphosphatidylcholine vesicles // Helv. Chim. Acta. 1986. V. 69. P. 12 - 24.
  60. Woodall A.A., Britton G., Jackson M.J. Carotenoids and protection of phospholipids in solution or in liposomes against oxidation by peroxyl radicals: relationship between carotenoid structure and protective ability // Biochim. Biophys. Acta. 1997. V. 1336. P. 575 - 586.
  61. Goodwin T.W. The Biochemistry of the Carotenoids, Volume II. Animals. London: Chapman and Hall. 1984. P. 173 - 195.
  62. Davies B.H. Carotenoid metabolism as a preparation for function // Pure. Appl. Chem. 1991. V. 63.P. 131 - 140.
  63. Olson J.A. The irresistible fascination of carotenoids and vitamin A // Am. J. Clin. Nutr. 1993. V. 57. P. 833 - 839.
  64. Blomhoff R., Green M.H., Norum R.R. Vitamin A: physiological and biochemical processing // Annu. Rev. Nutr. 1992. V. 12. P. 37 - 57.
  65. Packer L., Obermuller-Jevic U., Kraemer K. et al. Carotenoids and Retinoids: Molecular Aspects and Health Issues // AOCS Press, Champaign, IL. 2004. P. 22 - 54.
  66. Biesalski H.K., Schrezenmeir J., Weber P., Weiß H.E. In: Vitamine, Stuttgart: Georg Thieme Verlag. 1997. P. 193 ? 196.
  67. Von Lintig J., Vogt K. Filling the gap in vitamin A research // J. Biol. Chem. 2000. V. 275. P. 11915 - 11920.
  68. Kiefer C., Hessel S., Lampert J.M., et al. Identification and characterization of a mammalian enzyme catalyzing the asymmetric oxidative cleavage of provitamin A // J. Biol. Chem. 2001. V. 276. P. 14110 - 14116.
  69. Hoyos B., Hammerling U. Carotenoids and Retinoids: Molecular Aspects and Health Issues // AOCS Press., Champaign, IL. 2004. P. 42 - 44.
  70. Bone R.A., Landrum J.T., Tarsis S.L. Preliminary identification of the human macular pigment // Vision Res. 1985. V. 25. P. 1531 - 1535.
  71. Bone R.A., Landrum J.T., Hime G.W., Cains A. Stereochemistry of the human macular carotenoids // Invest. Ophthalmol. Vis. Sci. 1993. V. 34. P. 2033 - 2040.
  72. Khachik F., de Moura F.F., Zhao D-Y., et al. Transformations of selected carotenoids in serum, liver, and ocular tissues of humans and non-primate animal models // Invest. Ophthamol. Vis. Sci. 2002. V. 43. P. 3383 - 3392.
  73. Landrum J.T., Bone R.A. Lutein, zeaxanthin, and the macular pigment // Arch. Biochem. Biophys. 2001. V. 385. P. 28 - 40.