Biologic Activity of Carotenoids Related to Distinct Membrane Physicochemical Interactions

American Journal of Cardiology

Volumn 101, Issue 10 SUPPL., 2008, Pages

  McNulty, Hyesun ^a   Jacob, Robert F ^a   Mason, R Preston ^a,b  

^a ELUCIDA RESEARCH LLC   (United States)

^b BRIGHAM AND WOMEN S HOSPITAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASTAXANTHIN; BETA CAROTENE; CAROTENOID; LYCOPENE; MEMBRANE LIPID; POLYUNSATURATED FATTY ACID; XANTHOPHYLL; ZEAXANTHIN;

ANTIOXIDANT ACTIVITY; ARTICLE; CARDIOVASCULAR DISEASE; CLINICAL TRIAL; DRUG EFFECT; DRUG STRUCTURE; HUMAN; LIPID PEROXIDATION; MEMBRANE BINDING; MEMBRANE STRUCTURE; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; X RAY DIFFRACTION;

BETA CAROTENE; CARDIOVASCULAR DISEASES; CAROTENOIDS; ENDOTHELIUM, VASCULAR; HUMANS; LIPID PEROXIDATION; LUTEIN; OXIDATIVE STRESS; XANTHOPHYLLS;

EID: 43049168941     PISSN: 00029149     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.amjcard.2008.02.004     Document Type: Article

References (81)

1. Britton G. Carotenoids Handbook (2004), Birkhauser Verlag AG, Basel 5
2. Khachik F., Beecher G.R., and Smith Jr. J.C. Lutein, lycopene, and their oxidative metabolites in chemoprevention of cancer. J Cell Biochem Suppl 22 (1995) 236-246
3. McNulty H.P., Byun J., Lockwood S.F., Jacob R.F., and Mason R.P. Differential effects of carotenoids on lipid peroxidation due to membrane interactions: x-ray diffraction analysis. Biochim Biophys Acta 1768 (2007) 167-174
4. Di Mascio P., Kaiser S., and Sies H. Lycopene as the most efficient biological carotenoid singlet oxygen quencher. Arch Biochem Biophys 274 (1989) 532-538
5. Conn P.F., Schalch W., and Truscott T.G. The singlet oxygen and carotenoid interaction. J Photochem Photobiol B 11 (1991) 41-47
6. 2 radical. J Am Chem Soc 117 (1995) 8322-8326
7. Burton G.W., and Ingold K.U. Beta-carotene: an unusual type of lipid antioxidant. Science 224 (1984) 569-573
8. Everett S.A., Dennis M.F., Patel K.B., Maddix S., Kundu S.C., and Willson R.L. Scavenging of nitrogen dioxide, thiyl, and sulfonyl free radicals by the nutritional antioxidant β-carotene. J Biol Chem 271 (1996) 3988-3994
9. Mortensen A., and Skibsted L.H. Kinetics of parallel electron transfer from beta-carotene to phenoxyl radical and adduct formation between phenoxyl radical and beta-carotene. Free Radic Res 25 (1996) 515-523
10. Halliwell B. Oxidative stress, nutrition, and health: experimental strategies for optimization of nutritional antioxidant intake in humans. Free Radic Res 25 (1996) 57-74
11. Davies K.J. Oxidative stress: the paradox of aerobic life. Biochem Soc Symp 61 (1995) 1-31
12. Ziegler R.G., Mayne S.T., and Swanson C.A. Nutrition and lung cancer. Cancer Causes Control 7 (1996) 157-177
13. Mayne S.T. Beta-carotene, carotenoids, and disease prevention in humans. FASEB J 10 (1996) 690-701
14. Peto R., Doll R., Buckley J.D., and Sporn M.B. Can dietary beta-carotene materially reduce human cancer rates?. Nature 290 (1981) 201-208
15. Mathews-Roth M. Recent progress in the medical applications of carotenoids. Pure Appl Chem 63 (1991) 147-156
16. Halliwell B. Antioxidants and human disease: a general introduction. Nutr Rev 55 (1997) S44-S52
17. Vivekananthan D.P., Penn M.S., Sapp S.K., Hsu A., and Topol E.J. Use of antioxidant vitamins for the prevention of cardiovascular disease: meta-analysis of randomised trials. Lancet 361 (2003) 2017-2023
18. Tanaka T., Makita H., Ohnishi M., Mori H., Satoh K., and Hara A. Chemoprevention of rat oral carcinogenesis by naturally occurring xanthophylls, astaxanthin and canthaxanthin. Cancer Res 55 (1995) 4059-4064
19. Woodall A.A., Britton G., and 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 1336 (1997) 575-586
20. Gabrielska J., and Gruszecki W.I. Zeaxanthin (dihydroxy-beta-carotene) but not beta-carotene rigidifies lipid membranes: a 1H-NMR study of carotenoid-egg phosphatidylcholine liposomes. Biochim Biophys Acta 1285 (1996) 167-174
21. Sujak A., Gabrielska J., Grudzinski W., Borc R., Mazurek P., and Gruszecki W.I. Lutein and zeaxanthin as protectors of lipid membranes against oxidative damage: the structural aspects. Arch Biochem Biophys 371 (1999) 301-307
22. 13C-NMR study. Biochim Biophys Acta 1194 (1994) 143-148
23. Subczynski W.K., Markowska E., and Sielewiesiuk J. Spin-label studies on phosphatidylcholine-polar carotenoid membranes: effects of alkyl-chain length and unsaturation. Biochim Biophys Acta 1150 (1993) 173-181
24. Strzalka K., and Gruszecki W.I. Effect of beta-carotene on structural and dynamic properties of model phosphatidylcholine membranes. I. An EPR spin label study. Biochim Biophys Acta 1194 (1994) 138-142
25. Wisniewska A., and Subczynski W.K. Effects of polar carotenoids on the shape of the hydrophobic barrier of phospholipid bilayers. Biochim Biophys Acta 1368 (1998) 235-246
26. Rengel D., Diez-Navajas A., Serna-Rico A., Veiga P., Muga A., and Milicua J.C. Exogenously incorporated ketocarotenoids in large unilamellar vesicles: protective activity against peroxidation. Biochim Biophys Acta 1463 (2000) 179-187
27. Kostecka-Gugala A., Latowski D., and Strzalka K. Thermotropic phase behaviour of α-dipalmitoylphosphatidylcholine multibilayers is influenced to various extents by carotenoids containing different structural features-evidence from differential scanning calorimetry. Biochim Biophys Acta 1609 (2003) 193-202
28. Shibata A., Kiba Y., Akati N., Fukuzawa K., and Terada H. Molecular characteristics of astaxanthin and beta-carotene in the phospholipid monolayer and their distributions in the phospholipid bilayer. Chem Phys Lipids 113 (2001) 11-22
29. Socaciu C., Jessel R., and Diehl H.A. Competitive carotenoid and cholesterol incorporation into liposomes: effects on membrane phase transition, fluidity, polarity and anisotropy. Chem Phys Lipids 106 (2000) 79-88
30. Socaciu C., Jessel R., and Diehl H.A. Carotenoid incorporation into microsomes: yields, stability and membrane dynamics. Spectrochim Acta A Mol Biomol Spectrosc 56 (2000) 2799-2809
31. Socaciu C., Bojarski P., Aberle L., and Diehl H. Different ways to insert carotenoids into liposomes affect structure and dynamics of the bilayer differently. Biophys Chem 99 (2002) 1-15
32. Gruszecki W.I., and Sielewiesiuk J. Orientation of xanthophylls in phosphatidylcholine multibilayers. Biochim Biophys Acta 1023 (1990) 405-412
33. Sujak A., Mazurek P., and Gruszecki W.I. Xanthophyll pigments lutein and zeaxanthin in lipid multibilayers formed with dimyristoylphosphatidylcholine. J Photochem Photobiol B 68 (2002) 39-44
34. Emmelot P. The organization of the plasma membrane of mammalian cells: structure in relation to function. In: Jamieson G.A., and Robinson D.M. (Eds). Mammalian Cell Membranes (1977), Butterworths, Boston 1-54
35. Yeagle P.L. Cholesterol and the cell membrane. Biochim Biophys Acta 822 (1985) 267-287
36. Franks N.P., and Levine Y.K. Low-angle x-ray diffraction. Mol Biol Biochem Biophys 31 (1981) 437-487
37. Blaurock A.E. Evidence of bilayer structure and of membrane interactions from X-ray diffraction analysis. Biochim Biophys Acta 650 (1982) 167-207
38. Blaurock A.E. Structure of the nerve myelin membrane: proof of the low-resolution profile. J Mol Biol 56 (1971) 35-52
39. Moody M.F. X-ray diffraction pattern of nerve myelin: a method for determining the phases. Science 142 (1963) 1173-1174
40. Blaurock A.E., and Wilkins M.H. Structure of retinal photoreceptor membranes. Nature 236 (1972) 313-314
41. Corless J.M. Lamellar structure of bleached and unbleached rod photoreceptor membranes. Nature 237 (1972) 229-231
42. Knutton S., Finean J.B., Coleman R., and Limbrick A.R. Low-angle x-ray diffraction and electronmicroscope studies of isolated erythrocyte membranes. J Cell Sci 7 (1970) 357-371
43. Dupont Y., and Hasselbach W. Structural changes in sarcoplasmic reticulum membrane induced by SH reagents. Nat New Biol 246 (1973) 41-44
44. Worthington C.R., and Liu S.C. Structure of sarcoplasmic reticulum membranes at low resolution (17A). Arch Biochem Biophys 157 (1973) 573-579
45. Mason R.P., Tulenko T.N., and Jacob F.R. Direct evidence for cholesterol crystalline domains in biological membranes: role in human pathobiology. Biochim Biophys Acta 1610 (2003) 198-207
46. Herbette L., Marquardt J., Scarpa A., and Blasie J.K. A direct analysis of lamellar x-ray diffraction from hydrated oriented multilayers of fully functional sarcoplasmic reticulum. Biophys J 20 (1977) 245-272
47. van de Ven M., Kattenberg M., van Ginkel G., and Levine Y.K. Study of the orientational ordering of carotenoids in lipid bilayers by resonance-Raman spectroscopy. Biophys J 45 (1984) 1203-1209
48. Johansson L.B.A., Lindblom G., Wieslander A., and Arvidson G. Orientation of β-carotene and retinal in lipid bilayers. FEBS Lett 128 (1981) 97-99
49. Suwalsky M., Hidalgo P., Strzalka K., and Kostecks-Gugala A. Comparative x-ray studies on the interaction of carotenoids with a model phosphatidylcholine membrane. Z Naturforsch 57c (2002) 129-134
50. Gruszecki W.I. In: Frank H.A., Young A.J., Britton G., and Cogdell R.J. (Eds). The Photochemistry of Carotenoids (1999), Kluwer Academic, Dordrecht, Netherlands 363-379
51. Lazrak T., Milon A., Wolff G., Albrecht A.M., Miehe M., Ourisson G., and Nakatani Y. Comparison of the effects of inserted C40- and C50-terminally dihydroxylated carotenoids on the mechanical properties of various phospholipid vesicles. Biochim Biophys Acta 903 (1987) 132-141
52. Subczynski W.K., Markowska E., Gruszecki W.I., and Sielewiesiuk J. Effects of polar carotenoids on dimyristoylphosphatidylcholine membranes: a spin-label study. Biochim Biophys Acta 1105 (1992) 97-108
53. Chakrabarti A.C., and Deamer D.W. Permeability of lipid bilayers to amino acids and phosphate. Biochim Biophys Acta 1111 (1992) 171-177
54. Deamer D.W., and Bramhall J. Permeability of lipid bilayers to water and ionic solutes. Chem Phys Lipids 40 (1986) 167-188
55. Finkelstein A. Water and nonelectrolyte permeability of lipid bilayer membranes. J Gen Physiol 68 (1976) 127-135
56. Walter A., and Gutknecht J. Permeability of small nonelectrolytes through lipid bilayer membranes. J Membr Biol 90 (1986) 207-217
57. Altenbach C., Froncisz W., Hyde J.S., and Hubbell W.L. Conformation of spin-labeled melittin at membrane surfaces investigated by pulse saturation recovery and continuous wave power saturation electron paramagnetic resonance. Biophys J 56 (1989) 1183-1191
58. Snel M.M., and Marsh D. Accessibility of spin-labeled phospholipids in anionic and zwitterionic bilayer membranes to paramagnetic relaxation agents: continuous wave power saturation EPR studies. Biochim Biophys Acta 1150 (1993) 155-161
59. Subczynski W.K., Wisniewska A., Yin J.J., Hyde J.S., and Kusumi A. Hydrophobic barriers of lipid bilayer membranes formed by reduction of water penetration by alkyl chain unsaturation and cholesterol. Biochemistry 33 (1994) 7670-7681
60. Goto S., Kogure K., Abe K., Kimata Y., Kitahama K., Yamashita E., and Terada H. Efficient radical trapping at the surface and inside the phospholipid membrane is responsible for highly potent antiperoxidative activity of the carotenoid astaxanthin. Biochim Biophys Acta 1512 (2001) 251-258
61. Krinsky N.I., Landrum J.T., and Bone R.A. Biologic mechanisms of the protective role of lutein and zeaxanthin in the eye. Annu Rev Nutr 23 (2003) 171-201
62. Janero D., and Burghardt B. Prevention of oxidative injury to cardiac phospholipids by membrane-active "stabilizing agents". Res Commun Chem Path Pharm 36 (1989) 163-173
63. Hillard C.J., Harris R.A., and Bloom A.S. Effects of the cannabinoids on physical properties of brain membranes and phospholipid vesicles: fluorescence studies. J Pharmacol Exp Ther 232 (1985) 579-588
64. Nakazawa T., Nagatsuka S., and Yukawa O. Effects of membrane stabilizing agents and radiation on liposomal membranes. Drugs Exp Clin Res 12 (1986) 831-835
65. Berglund A., Nilsson R., and Liljenberg C. Permeability of large unilamellar digalactosyldiacylglycerol vesicles for protons and glucose-influence of α-tocopherol, β-carotene, zeaxanthin and cholesterol. 1999. Plant Physiol Biochem 37 (1999) 179-186
66. Subczynski W.K., Markowska E., and Sielewiesiuk J. Effect of polar carotenoids on the oxygen diffusion-concentration product in lipid bilayers: an EPR spin label study. Biochim Biophys Acta 1068 (1991) 68-72
67. Subczynski W.K., Hyde J.S., and Kusumi A. Oxygen permeability of phosphatidylcholine-cholesterol membranes. Proc Natl Acad Sci U S A 86 (1989) 4474-4478
68. Palozza P., and Krinsky N.I. Astaxanthin and canthaxanthin are potent antioxidants in a membrane model. Arch Biochem Biophys 297 (1992) 291-295
69. Woodall A.A., Britton G., and Jackson M.J. Antioxidant activity of carotenoids in phosphatidylcholine vesicles: chemical and structural considerations. Biochem Soc Trans 23 (1995) 133S
70. el-Saadani M., Esterbauer H., el-Sayed M., Goher M., Nassar A.Y., and Jurgens G. A spectrophotometric assay for lipid peroxides in serum lipoproteins using a commercially available reagent. J Lipid Res 30 (1989) 627-630
71. Terao J. Antioxidant activity of beta-carotene-related carotenoids in solution. Lipids 24 (1989) 659-661
72. 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. Lack of effect of long-term supplementation with beta carotene on the incidence of malignant neoplasms and cardiovascular disease. N Engl J Med 334 (1996) 1145-1149
73. Lee I.M., Cook N.R., Manson J.E., Buring J.E., and Hennekens C.H. β-carotene supplementation and incidence of cancer and cardiovascular disease: the Women's Health Study. J Natl Cancer Inst 91 (1999) 2102-2106
74. Omenn G.S., Goodman G.E., Thornquist M.D., Balmes J., Cullen M.R., Glass A., Keogh J.P., Meyskens F.L., Valanis B., Williams J.H., Barnhart S., and Hammar S. Effects of a combination of beta carotene and vitamin A on lung cancer and cardiovascular disease. N Engl J Med 334 (1996) 1150-1155
75. The Alpha-Tocopherol, Beta Carotene Cancer Prevention Study Group. The effect of vitamin E and beta carotene on the incidence of lung cancer and other cancers in male smokers. N Engl J Med 330 (1994) 1029-1035
76. Brown B.G., Zhao X.Q., Chait A., Fisher L.D., Cheung M.C., Morse J.S., Dowdy A.A., Marino E.K., Bolson E.L., Alaupovic P., Frohlich J., and Albers J.J. Simvastatin and niacin, antioxidant vitamins, or the combination for the prevention of coronary disease. N Engl J Med 345 (2001) 1583-1592
77. Beutner S., Bloedorn B., Frixel S., Blanco I.H., Hoffmann T., Martin H., Mayer B., Noack P., Ruck C., Schmidt M., et al. Quantitative assessment of antioxidant properties of natural colorants and phytochemicals: carotenoids, flavonoids, phenols and indigoids: the role of β-carotene in antioxidant functions. J Sci Food Agricult 81 (2001) 559-568
78. Martin H.D., Jäger C., Ruck C., and Schmidt M. Anti- and prooxidant properties of carotenoids. J Prakt Chem 341 (1999) 302-308
79. Gross G.J., Hazen S.L., and Lockwood S.F. Seven day oral supplementation with Cardax (disodium disuccinate astaxanthin) provides significant cardioprotection and reduces oxidative stress in rats. Mol Cell Biochem 283 (2006) 23-30
80. Gross G.J., and Lockwood S.F. Acute and chronic administration of disodium disuccinate astaxanthin (Cardax) produces marked cardioprotection in dog hearts. Mol Cell Biochem 272 (2005) 221-227
81. Lauver D.A., Lockwood S.F., and Lucchesi B.R. Disodium disuccinate astaxanthin (Cardax) attenuates complement activation and reduces myocardial injury following ischemia/reperfusion. J Pharmacol Exp Ther 314 (2005) 686-692