Inclusion complexes of cyclodextrins with galangin: A thermodynamic and reactivity study

Journal of Solution Chemistry

Volumn 39, Issue 8, 2010, Pages 1168-1177

  Jullian, Carolina ^a   Alfaro, Muriel ^a   Zapata Torres, Gerald ^a   Olea Azar, Claudio ^a  

^a UNIVERSITY OF CHILE   (Chile)

Author keywords

Cyclodextrins; Docking; Galangin; Inclusion complex; ORAC FL; Thermodynamic study

Indexed keywords

EID: 78049280122     PISSN: 00959782     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10953-010-9574-1     Document Type: Article

References (27)

1. P.C. Hollman M.B. Katan 1997 Absorption, metabolism and health effects of dietary flavonoids in man Biomed. Pharmacother. 51 305 310 1:CAS:528: DyaK2sXntlSqtrw%3D 10.1016/S0753-3322(97)88045-6 (Pubitemid 27423753)
2. B. Stavric 1994 Antimutagens and anticarcinogens in foods Food Chem. Toxicol. 32 79 90 1:CAS:528:DyaK2cXis1ygu70%3D 10.1016/0278-6915(84)90040-1 (Pubitemid 24131124)
3. Kochhar, S.P.: Deterioration of edible oils, fats and foodstuffs. In: Scott, G. (ed.): Atmospheric Oxidation and Antioxidants, pp. 71-139. Elsevier Science, Amsterdam (1993)
4. M.G.L. Hertog E.J.M. Feskens D. Kromhout 1997 Antioxidant flavonols and coronary heart disease risk Lancet 349 699 699 1:STN:280:DyaK2s3jt12ksg%3D%3D 10.1016/S0140-6736(05)60135-3
5. M.Y. Heo J.H. Lee S.J. Sohn W.W. Au 1996 Anticlastogenic effects of galangin against mitomycin C-induced micronuclei in reticulocytes of mice Mutat. Res. 360 37 41 1:CAS:528:DyaK28XjtFensrY%3D
6. M.E. Wall M.C. Wani G. Manikumar P. Abraham H. Taylor T.J. Hughes J. Warner R. McGiveney 1988 Plant antimutagenic agents. 2. Flavonoids J. Nat. Prod. 51 1084 1091 1:CAS:528:DyaL1MXnt1Ggsg%3D%3D 10.1021/np50060a006 (Pubitemid 19026540)
7. M.R. Cholbi M. Paya M.J. Alcaraz 1991 Inhibitory effects of phenolic compounds on CCl4-induced microsomal lipid peroxidation Experientia 47 195 199 1:CAS:528:DyaK3MXhsFKlsr0%3D 10.1007/BF01945426
8. Y. Imamura T. Migita Y. Uriu M. Otagiri T. Okawara 2000 Inhibitory effects of flavonoids on rabbit heart carbonyl reductase J. Biochem. 127 653658
9. H. Shih G.V. Pickwell L.C. Quattrochi 2000 Differential effects of flavonoid compounds on tumor promoter-induced activation of the human CYP1A2 enhancer Arch. Biochem. Biophys. 373 287 294 1:CAS:528:DC%2BD3cXosVCj 10.1006/abbi.1999.1550 (Pubitemid 30046517)
10. Szejtli, J.: Cyclodextrin Technology. Kluwer Academic, Dordrecht (1988)
11. H.J. Buschmann E. Schollmayer 2002 Application of cyclodextrins in cosmetic products: a review J. Cosmet. Sci. 53 185 191 1:CAS:528: DC%2BD38XovFWgsro%3D
12. T. Loftsson M.E. Brewster 1996 Pharmaceutical application of cyclodextrins: drug solubilisation and stabilization J. Pharm. Sci. 85 1017 1025 1:CAS:528:DyaK28XlsFSrsr4%3D 10.1021/js950534b (Pubitemid 26338912)
13. E. Alvarez-Parrilla L.A. De la Rosa F. Torres-Rivas J. Rodrigo-Garcia G.A. Gonzalez-Aguilar 2005 Complexation of apple antioxidants: chlorogenic acid, quercetin and rutin by β-cyclodextrin (β-CD) J. Incl. Phenom. Macrocycl. Chem. 53 121 129 1:CAS:528:DC%2BD2MXmtlWis7k%3D 10.1007/s10847-005- 1620-z (Pubitemid 41016368)
14. C. Jullian T. Orosteguis F. Pérez-Cruz P. Sánchez F. Mendizabal C. Olea-Azar 2008 Spectrochim. Acta A 71 269 275 10.1016/j.saa.2007. 12.020
15. R. Ficarra S. Tommasini D. Raneri M.L. Calabrò M.R. Di Bella C. Rustichelli M.C. Gamberini P. Ficarra 2002 Study of flavonoids/β- cyclodextrins inclusion complexes by NMR, FT-IR, DSC, X-ray investigation J. Pharm. Biomed. Anal. 29 1005 1014 1:CAS:528:DC%2BD38XltFWjurg%3D 10.1016/S0731-7085(02)00141-3 (Pubitemid 34756653)
16. B. Ou M. Hampsch-Woodill R.L. Prior 2001 Development and validation of an improved oxygen radical absorbance capacity assay using fluorescein as the fluorescent probe J. Agric. Food Chem. 49 4619 4626 1:CAS:528: DC%2BD3MXmvVSgtLo%3D 10.1021/jf010586o (Pubitemid 32988695)
17. A. Dávalos C. Gómez-Cordovés B. Bartolomé 2004 Extending applicability of the oxygen radical absorbance capacity (ORACFluorescein) assay J. Agric. Food Chem. 52 48 54 10.1021/jf0305231
18. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Montgomery, J.A., Stratmann, R.E., Burant, J.C., Dapprich, S., Millam, J.M., Daniels, A.D., Kudin, K.N., Strain, M.C., Farkas, O., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Cliford, S., Ochterski, J., Petersson, G.A., Ayala, P.Y., Cui, Q., Morokuma, K., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Cioslowski, J., Ortiz, J.V., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Gonzalez, C., Challacombe, M., Gill, P.M.W., Johnson, B.G., Chen, W., Wong, M.W., Andres, J.L., Head-Gordon, M., Replogle, E.S., Pople, J.A.: Gaussian 98 (revision a.7) (1998)
19. G.M. Morris D.S. Goodsell R.S. Halliday R. Huey W.E. Hart R.K. Belew A.J. Olson 1998 Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function J. Comput. Chem. 19 1639 1662 1:CAS:528:DyaK1cXntFemur4%3D 10.1002/(SICI)1096-987X(19981115)19:14<1639:: AID-JCC10>3.0.CO;2-B
20. C. Jullian 2009 Improvement of galangin solubility using native and derivative cyclodextrins. An UV-vis and NMR study J. Chil. Chem. Soc. 54 201 203 1:CAS:528:DC%2BD1MXovV2lsLY%3D 10.4067/S0717-97072009000200025
21. M.C. Bergonzi A.R. Bilia L. Di Bar G. Mazzi F.F. Vincieri 2007 Studies on the interactions between some flavonols and cyclodextrins Bioorg. Med. Chem. Lett. 17 5744 5748 1:CAS:528:DC%2BD2sXhtFSit73O 10.1016/j.bmcl.2007.08.067 (Pubitemid 47446234)
22. H. Kim J. Choi S.J. Jung 2009 Inclusion complexes of modified cyclodextrins with some flavonols J. Incl. Phenom. Macrocycl. Chem. 64 43 47 1:CAS:528:DC%2BD1MXlslWntbo%3D 10.1007/s10847-009-9534-9
23. A. Mounoz de la Pena T.T. Ndou J.B. Zung K.L. Greene D.H. Live I.M. Warner 1991 Alcohol size as a factor in the ternary complexes formed with pyrene and beta-cyclodextrin J. Am. Chem. Soc. 113 1572 1577 10.1021/ja00005a019
24. Q. Zhang Z. Jiang Y. Guo R. Li 2008 Complexation study of brilliant cresyl blue with β-cyclodextrin and its derivatives by UV-vis and fluorospectrometry Spectrochim. Acta A 69 65 70 10.1016/j.saa.2007.03.009 (Pubitemid 350297051)
25. C. Jullian C. Cifuentes M. Alfaro S. Miranda G. Barriga C. Olea-Azar 2010 Spectroscopic characterization of the inclusion complexes of luteolin with native and derivatized β-cyclodextrin Bioorg. Med. Chem. 14 5025 5031 10.1016/j.bmc.2010.05.079
26. D. Huang B. Ou M. Hampsch-Woodill J.A. Flanagan E.K. Deemer 2002 Development and validation of oxygen radical absorbance capacity assay for lipophilic antioxidants using randomly methylated β-cyclodextrin as the solubility enhancer J. Agric. Food Chem. 50 1815 1821 1:CAS:528: DC%2BD38XhtVKitL0%3D 10.1021/jf0113732 (Pubitemid 34259972)
27. X. Wu L. Gu J. Holden D.B. Haytowitz S.E. Gebhardt G. Beecher R.L. Prior 2004 Development of a data base for total antioxidant capacity in foods: a preliminary study J. Food Compos. Anal. 17 407 422 1:CAS:528: DC%2BD2cXksVanurg%3D 10.1016/j.jfca.2004.03.001 (Pubitemid 38787196)