A comparative study of the molecular lipophilicity indices of vitamins A and E, and of some precursors of vitamin A, estimated by HPLC and by different computation methods

• Autorzy: Briciu R. D. , Kot-Wasik A. , Namieśnik J. , Sârbu C.
• Języki publikacji: EN

Abstrakty

EN

Lipophilicity indices for vitamins A and E, and for some precursors of vitamin A, have been determined for the first time by reversed-phase high-performance liquid chromatography (RPHPLC) on C 18 and C 8 columns. For each column the mobile phases were methanol-water mixtures with methanol in volume proportions from 86 to 90% ( υ/υ ) in 1% steps. The regression correlation coefficients obtained for both stationary phases were excellent (usually >0.999). To compare the experimental lipophilicity estimated for the compounds by use of log k′ w , S , φ 0 , the means of k′ and log k′ , and the scores of k′ and log k′ corresponding to the first principal component, and log P values calculated by use of different computer software a correlation matrix was constructed. Better correlations were obtained in both cases between the mean of k′ and the mean of log k′ , and scores corresponding to the first principal component obtained by applying principal-components analysis to the matrix of retention factors and computed log P values. The best correlations were found between the mean of k′ and scores corresponding to the first principal component determined on C 8 and most of the computed log P values.

Słowa kluczowe

EN

vitamins; carotenoids; lipophilicity; lipophilicity indices; HPLC; PCA

• Wydawca: University of Silesia in Katowice ; Akademiai Kiado
• Czasopismo: Acta Chromatographica
• Rocznik: 2009
• Tom: Vol. 21, no. 2
• Strony: 237--250
• Opis fizyczny: Bibliogr. 31 poz., rys., tab.

Twórcy

autor

Briciu R. D.

• Babeş-Bolyai University Faculty of Chemistry and Chemical Engineering Arany Janos Str. No 11 RO-400028 Cluj Napoca Romania

autor

Kot-Wasik A.

• Gdańsk University of Technology Chemical Faculty Narutowicza Str. No 11/12 80-952 Gdańsk Poland

autor

Namieśnik J.

• Gdańsk University of Technology Chemical Faculty Narutowicza Str. No 11/12 80-952 Gdańsk Poland

autor

Sârbu C.

• Babeş-Bolyai University Faculty of Chemistry and Chemical Engineering Arany Janos Str. No 11 RO-400028 Cluj Napoca Romania

Bibliografia

• [1] R. Blomhoff, Vitamin A in Health and Disease, Marcel Dekker, New York, 1994
• [2] M. Raju, S. Varakumar, R. Lakshminarayana, T.P. Krishnakantha, and V. Baskaran, Food. Chem., 101 , 1598 (2007)
• [3] N.I. Krinsky, Pure Appl. Chem., 66 , 1003 (1994)
• [4] W. Stahl, S. Nicolai, K. Briviba, M. Hanusch, G. Broszeit, M. Peters, H.-D. Martin, and H. Sies, Carcinogenesis, 18 , 89 (1997)
• [5] L. Packer and J. Fuchs, Vitamin E in Health and Disease, Marcel Dekker, New York, 1993
• [6] R. Cazzola, G. Cervato, and B. Cestaro, J. Nutr. Sci. Vitaminol., 45 , 39 (1999)
• [7] J. Sangster, Octanol-Water Partition Coefficients: Fundamentals and Physical Chemistry, John Wiley and Sons, New York, 1997
• [8] C. Hansch and A. Leo, Exploring QSAR. Fundamentals and Applications in Chemistry and Biology, ACS, Washington, DC, 1995
• [9] M. Karelson, Molecular Descriptors in QSAR/QSPR, John Wiley and Sons, New York, 2000
• [10] R. Kaliszan, Structure and Retention in Chromatography: A Chemometric Approach, Harwood Academic Publishers, Amsterdam, 1997
• [11] R.F. Rekker and R. Mannhold, Calculation of Drug Lipophilicity: The Hydrophobic Fragmental Constant Approach, VCH, Weinheim, 1992
• [12] J.F.K. Huber, C.A.H. Meijers, and J.A.R.J. Hulsman, Anal. Chem., 44 , 111 (1972)
• [13] A. Kaune, M. Knorrenschild, and A. Kettrup, Fresenius J. Anal. Chem., 352 , 3030 (1995)
• [14] A. Paschke, M. Manz, and G. Schüürmann, Chemosphere, 45 , 721 (2001)
• [15] http://www.metabolomics.ca
• [16] L.R. Snyder, J.W. Dolan, and J.R. Gant, J. Chromatogr., 165 , 3 (1979)
• [17] H.A. Cooper and R.J. Hurutbise, J. Chromatogr., 360 , 313 (1986)
• [18] C. Giaginis and A. Tsantili-Kakoulidou, J. Liq. Chromatogr. Related Technol., 31 , 79 (2008)
• [19] K. Valkó and P. Segel, J. Chromatogr., 631 , 49 (1993)
• [20] C. My Du, K. Valkó, C. Bevan, and D. Reynolds, Anal. Chem., 70 , 4228 (1997)
• [21] C. Sârbu and S. Todor, J. Planar Chromatogr., 11 , 123 (1998)
• [22] C. Sârbu and S. Todor, J. Chromatogr. A, 822 , 263 (1998)
• [23] C. Sârbu, D. Casoni, M. Dărăbanţu, and C. Maiereanu, J. Pharm. Biomed. Anal., 35 , 213 (2004)
• [24] HyperChem, release 7.5 for Windows, Molecular Modeling System; Hypercube, and Autodesk
• [25] http://www.tripos.com
• [26] http://www.cambridgesoft.com
• [27] http://www.talete.mi.it
• [28] I.V. Tetko, J. Gasteiger, R. Todeschini, A. Mauri, D. Livingstone, P. Ertl, V.A. Palyulin, E.V. Radchenko, N.S. Zefirov, A.S. Makarenko, V.Y. Tanchuk, and V.V. Prokopenko, J. Comput. Aid. Mol. Des., 19 , 453 (2005)
• [29] http://www.vcclab.org
• [30] G.L. Biagi, A.M. Barbaro, M.C. Guerra, G. Gantelli-Forti, and M.E. Fracasso, J. Med. Chem., 17 , 28 (1974)
• [31] P.J. Schoenmakers, H.A.H. Billiet, and L. de Galan, J. Chromatogr., 185 , 179 (1979)