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Journal
2006 | 4 | 3 | 489-501
Article title

Surface properties of some carotenoids spread in monolayers at the air/water interface. Experimental and computational approach

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EN
Abstracts
EN
The surface pressure versus molecular area isotherms of some carotenoids: β,β-carotene-4-one (echinenone, ECH), β,β-carotene-4,4′-dione (canthaxanthin, CAN) and 4,4′-diapo-ω,ω-carotene-4,4′-dial (APO), spread at the air/water interface, are reported. A van der Waals type state equation is used to describe the high molecular area portions of the compression isotherms and interaction parameters within monolayers are derived. Quantum chemical semi-empirical SCF MO calculations (AM1 and PM3) are performed for the optimized geometries of molecules and dipole moments are calculated. Similar theoretical magnitudes are obtained by both methods. Surface properties, like collapse pressure, surface compressional modulus and interaction parameters are discussed in terms of dipole-dipole interactions, and correlations with the calculated quantities for the carotenoid molecules are analyzed. The orientation of the different carotenoid molecules in the monolayer is discussed.
Publisher

Journal
Year
Volume
4
Issue
3
Pages
489-501
Physical description
Dates
published
1 - 9 - 2006
online
1 - 9 - 2006
Contributors
author
  • Department of Physical Chemistry, “Babes-Bolyai” University of Cluj-Napoca, 400028, Cluj-Napoca, Romania
  • Department of Orthopaedic Surgery, “Iuliu Hatieganu” University of Medicine, 400015, Cluj-Napoca, Romania
author
  • Department of Physical Chemistry, “Babes-Bolyai” University of Cluj-Napoca, 400028, Cluj-Napoca, Romania
author
  • Department of Physical Chemistry, “Babes-Bolyai” University of Cluj-Napoca, 400028, Cluj-Napoca, Romania
  • Department of Physical Chemistry, “Babes-Bolyai” University of Cluj-Napoca, 400028, Cluj-Napoca, Romania
  • Department of Physical Chemistry, “Babes-Bolyai” University of Cluj-Napoca, 400028, Cluj-Napoca, Romania, mcotisel@yahoo.com
References
  • [1] M. Tomoaia-Cotişel and P.J. Quinn, Chapter 10: “Biophysical Properties of Carotenoids”. In: P.J. Quinn and V. Kagan (Eds.): Subcellular Biochemistry, Vol.30: Fat-Soluble Vitamins, Plenum Press, New York, 1998, pp. 219–242.
  • [2] E. Chifu, J. Zsakó and M. Tomoaia-Cotişel, “Xanthophyll films. I. Single-component monolayers at the air/water interface”, J. Colloid Interface Sci., Vol. 95, (1983), pp. 346–354. http://dx.doi.org/10.1016/0021-9797(83)90194-7[Crossref]
  • [3] M. Tomoaia-Cotişel and E. Chifu, “Xanthophyll films. II. Two-component monolayers of some xanthophylls and egg lecithin at the air/water interface”, J. Colloid Interface Sci., 95, (1983), pp. 355–361. http://dx.doi.org/10.1016/0021-9797(83)90195-9[Crossref]
  • [4] M. Tomoaia-Cotişel, J. Zsakó, E. Chifu and P. J. Quinn, “Intermolecular interactions in lipid-carotenoid monolayers”, Biochem. J., 248, (1987), pp. 877–882.
  • [5] C. N. N’soukpoe-Kossi, J. Sielewiesiuk, R.M. Leblanc, R.A. Bone and J. T. Landrum, “Linear dichroism and orientational studies of carotenoid Langmuir-Blodgett films”, Biochim. Biophys. Acta, Vol. 940, (1988), pp. 255–265. http://dx.doi.org/10.1016/0005-2736(88)90200-3[Crossref]
  • [6] J. Zsakó, M. Tomoaia-Cotişel and E. Chifu, “Insoluble mixed monolayers. V. Molecular associations in binary films: The regular association approach”, J. Colloid Interface Sci., Vol. 146, (1991), pp. 353–362. http://dx.doi.org/10.1016/0021-9797(91)90200-R[Crossref]
  • [7] R. Edge, E.J. Land, M. Rozanowska, T. Sarma and T.G. Truscott, “Carotenoid radical-melanin interactions”, J. Phys. Chem., B, Vol. 104, (2000), pp. 7193–7196. http://dx.doi.org/10.1021/jp9941561[Crossref]
  • [8] . A. Sujak, W. Okulski and W.I. Gruszecki, “Organisation of xanthophyll pigments lutein and zeaxanthin in lipid membranes formed with dipalmitoyl phosphatidylcholine”, Biochim. Biophys. Acta, Vol. 1509, (2000), pp. 255–263. http://dx.doi.org/10.1016/S0005-2736(00)00299-6[Crossref]
  • [9] W. Okulski, A. Sujak and W. I. Gruszecki, “Dipalmitoyl phosphatidylcholine membranes modified with zeaxanthin: numeric study of membrane organisation”, Biochim. Biophys. Acta, Vol. 1509 (2000), pp. 216–228. http://dx.doi.org/10.1016/S0005-2736(00)00298-4[Crossref]
  • [10] A. Shibata, Y. Kiba, N. Akati, K. Fukuzawa and H. Terada, “Molecular characteristics of astaxanthin and β-carotene in the phospholipid monolayer and their distributions in the phospholipid bilayer”, Chem. Phys. Lipids, Vol. 113, (2001), pp. 11–22. http://dx.doi.org/10.1016/S0009-3084(01)00136-0[Crossref]
  • [11] J. M. Humphries and F. Khachik, “Distribution of lutein, zeaxanthin, and related geometrical isomers in fruit, vegetables, wheat and pasta products”, J. Agric. Food Chem., Vol. 51, (2003), pp. 1322–1327. http://dx.doi.org/10.1021/jf026073e[Crossref]
  • [12] S. Liu, I.M. Lee, U. Ajani, S.R. Cole, J.E. Buring and J.E. Manson,. “Intake of vegetables rich in carotenoids and risk of coronary heart disease in men”, International J of Epidemiology, Vol. 30, (2001), pp. 130–135. http://dx.doi.org/10.1093/ije/30.1.130[Crossref]
  • [13] S.K. Osganian, M.J. Stampfer, E. Rimm, D. Spiegelman, J.E. Manson and W.C. Willet, “Dietary carotenoids and risk of coronary artery disease in women”. Am. J. Clin. Nutr. Vol. 77, (2003), pp. 1390–1399.
  • [14] N. Singhal and J. Austin, Micronutrients and HIV Infection, 2002, CRC Press, Boca Raton, 2000
  • [15] H. Nishino, H. Tokuda, Y. Satomi, M. Masuda, et al., “Cancer prevention by carotenoids”, Pure Appl. Chem., Vol. 71, (1999), 2273–2278.
  • [16] H. Nishino, M. Murakoshi, X.Y. Mou, S. Wada, M. Masuda, Y. Ohsaka, Y. Satomi and K. Jinno, “Cancer prevention by phytochemicals”, Oncology, Vol. 69,Suppl 1 (2005), pp. 38–40. http://dx.doi.org/10.1159/000086631[Crossref]
  • [17] J. Zsako, M. Tomoaia-Cotisel and E. Chifu, “Discussion of compression Isotherms of some carotenoid monolayers on the basis of HMO calculations”, In K.L. Mittal (Ed.): Surfactants in Solution, Vol. 9, Plenum Press, New York, 1989, pp 311–324.
  • [18] M. Tomoaia-Cotisel, C. Racz, G. Tomoaia, C. Floare, R. Totos, L. Bobos, O. Pascu and A. Dumitru, “Molecular structure and monolayer properties of some carotenoids”, Studia Univ. Babes-Bolyai, Chem., Vol. 50, (2005), pp. 39–45.
  • [19] J. Zsakó, V. Neagu, M. Tomoaia-Cotişel and E. Chifu, “Molecular structure and monolayer properties”, Rev. Roumaine Chim., Vol. 32, (1987), pp. 739–748.
  • [20] M. Tomoaia-Cotişel, J. Zsakó, M. Sălăjan and E. Chifu, “Interaction of unimolecular films of some carotenoids with electrolytes at the air/water interface”, in A. Pullman, V. Vasilescu, and L. Packer (Eds.): Water and Ions in Biological Systems, Union of Societies for Medical Sciences, Bucharest, 1985, pp. 371–381.
  • [21] E. Chifu, J. Zsakó, M. Tomoaia-Cotişel, M. Sălăjan and I. Albu, “Xanthophyll films. IV. Interaction of zeaxanthin and astaxanthin with electrolytes at the air/water interface”, J. Colloid Interface Sci., Vol. 112, (1986), pp. 241–251. http://dx.doi.org/10.1016/0021-9797(86)90088-3[Crossref]
  • [22] E. Chifu, M. Sălăjan, M. Tomoaia-Cotişel, I. Demeter-Vodnár and J. Zsakó, “Interactions of some biologically active compound monolayers with electrolytes at the air/water interface”, Studia Univ. Babes-Bolyai, Chem., Vol. 32, (1987), pp. 50–57.
  • [23] M. Tomoaia-Cotişel, J. Zsakó, M. Sălăjan and E. Chifu, “Surface complexes of xanthophyll films with transition metal ions”, Rev. Roum. Morphol. Embryol. Physiol., Physiology, Vol. 26, (1989), pp. 341–347.
  • [24] Yu.B. Vysotsky, V.S. Bryantsev, V.B. Fainerman, D. Vollhardt and R. Miller, “Quantum chemical semi-empirical approach to the thermodynamic characteristics of oligomers and large aggregates of alcohols at the water/air interface”, Colloids Surfaces, A, Vol. 209, (2002), pp. 1–14. http://dx.doi.org/10.1016/S0927-7757(02)00169-3[Crossref]
  • [25] Yu.B. Vystosky, V.S. Bryantsev, V.B. Fainerman, D. Vollhardt, R. Miller and E.V. Aksenenko, “Transition state for aggregation and reorganization of normal fatty alcohols at the air/water interface”, J. Phys. Chem. B, Vol. 108, (2004), pp. 8330–8337. http://dx.doi.org/10.1021/jp030884j[Crossref]
  • [26] Yu.B. Vysotsky, V.S. Bryantsev, D. Vollhardt, R. Miller and V.B. Fainerman, “Aggregation and re-organization of normal fatty alcohols at the air/water interface. PM3 molecular orbital approximation”, Colloids Surfaces, A, Vol. 239, (2004), pp. 135–140. http://dx.doi.org/10.1016/j.colsurfa.2003.09.029[Crossref]
  • [27] Yu.B. Vysotsky, V.S. Bryantsev, F.L. Boldyreva, V.B. Fainerman and D. Vollhardt, “Quantum chemical semi-empirical approach to the structural and thermodynamic characteristics of fluoroalkanols the air/water interface”, J. Phys. Chem. B, Vol. 109, (2005), pp. 454–462. http://dx.doi.org/10.1021/jp048240e[Crossref]
  • [28] A. Streitwieser: Molecular Orbital Theory for Organic Chemistry, Wiley, New York, 1961.
  • [29] O. Isler, Carotenoids, Birkhäuser Verlag, Basel, 1971.
  • [30] G. Britton, S. Liaaen-Jensen and H. Pfander (Eds.): The Carotenoid Series: Vol. 1a, Isolation and Analysis; Vol. 1b, Spectroscopy, Birkhäuser Verlag, Basle, 1995
  • [31] J. Zsakó, E. Chifu and M. Tomoaia-Cotişel, “Rotating rigid-plate model of carotenoid molecules and the behavior of their monolayers at the air/water interface”, Gazz. Chim. Ital., Vol. 109, (1979), pp. 663–668.
  • [32] M.J.S. Dewar, E.G. Zoebisch, E.F. Healy and J.J.P. Stewart, “Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model”, J. Amer. Chem. Soc., Vol. 107, (1985), pp. 3902–3909 http://dx.doi.org/10.1021/ja00299a024[Crossref]
  • [33] J.J.P. Stewart, “Optimization of parameters for semi-empirical methods. 1. Method.”, J. Comput. Chem., Vol. 10, (1989), pp. 209–220 http://dx.doi.org/10.1002/jcc.540100208[Crossref]
  • [34] HyperChem7.5 Molecular Modeling System, Hypercube Inc., Gainesville, 2002.
Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_s11532-006-0017-1
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