350 руб
Журнал «Вопросы биологической, медицинской и фармацевтической химии» №9 за 2013 г.
Статья в номере:
Структура и биологические функции каротиноидов (обзор)
Авторы:
С.В. Печинский - к. фарм. н., преподаватель, кафедра фармацевтической химии, Пятигорский медико-фармацевтический институт - филиал Волгоградского государственного медицинский университета. E-mail: hplc@yandex.ru А.Г. Курегян - к.фарм.н., ст. преподаватель, кафедра фармацевтической химии, Пятигорский медико-фармацевтический институт - филиал Волгоградского государственного медицинский университета. E-mail: Kooreguan@mail.ru
Аннотация:
Рассмотрены вопросы взаимосвязи строения и биологического действия каротиноидов. Показаны следующие аспекты: номенклатура каротиноидов, влияние изомерии на биологическую активность каротиноидов, взаимодействие каротиноидов со светом, фотопротекторная и антиоксидантная активность каториноидов, каротиноиды в мембранах клеток, биологическая роль продуктов окисления некоторых каротиноидов.
Страницы: 4-14
Список источников

  1. Бриттон Г. Биохимия природных пигментов // М.: Мир. 1986. 422 с.
  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. Р. 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. Р. 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.