Strategies to improve the solubility and stability of stilbene antioxidants: A comparative study between cyclodextrins and bile acids

Food Chemistry

Volumn 145, Issue , 2014, Pages 115-125

  Silva, Filomena ^a   Figueiras, Ana ^a,b   Gallardo, Eugenia ^a   Nerín, Cristina ^c   Domingues, Fernanda C ^a  

^a UNIVERSITY OF BEIRA INTERIOR   (Portugal)

^b UNIVERSITY OF COIMBRA   (Portugal)

^c UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

Bile salts; Cyclodextrins; HPLC DAD; Inclusion complexes; Micelles; Photostability; Stilbenes

Indexed keywords

BILE SALTS; HPLC-DAD; INCLUSION COMPLEX; PHOTO-STABILITY; STILBENES;

DIFFERENTIAL SCANNING CALORIMETRY; FOURIER TRANSFORM INFRARED SPECTROSCOPY; MICELLES; SALTS; SOLUBILITY; X RAY DIFFRACTION;

CYCLODEXTRINS;

ANTIOXIDANT; BILE ACID; CYCLODEXTRIN; HYDROPROPYL CYCLODEXTRIN; PINOSYLVIN; STILBENE; UNCLASSIFIED DRUG; PTEROSTILBENE; RESVERATROL; SOLUTION AND SOLUBILITY; STILBENE DERIVATIVE;

ARTICLE; COMPARATIVE STUDY; CONTROLLED STUDY; DIFFERENTIAL SCANNING CALORIMETRY; FOOD PACKAGING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; SOLUBILITY; STOICHIOMETRY; X RAY DIFFRACTION; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUTION AND SOLUBILITY;

ANTIOXIDANTS; BILE ACIDS AND SALTS; CALORIMETRY, DIFFERENTIAL SCANNING; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLODEXTRINS; MAGNETIC RESONANCE SPECTROSCOPY; SOLUBILITY; SOLUTIONS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STILBENES; X-RAY DIFFRACTION;

EID: 84883463227     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2013.08.034     Document Type: Article

References (50)

1. N.Y. Anisimova, M.V. Kiselevsky, A.V. Sosnov, S.V. Sadovnikov, I.N. Stankov, and A.A. Gakh Trans-, cis-, and dihydro-resveratrol: a comparative study Chemistry Central Journal 5 2011 88 93
2. M. Atanackovic, M. Posa, H. Heinle, L. Gojkovic-Bukarica, and J. Cvejic Solubilization of resveratrol in micellar solutions of different bile acids Colloids Surface B Biointerfaces 72 1 2009 148 154
3. V. Bertacche, N. Lorenzi, D. Nava, E. Pini, and C. Sinco Host-guest interaction study of resveratrol with natural and modified cyclodextrins Journal of Inclusion Phenomena and Macrocyclic Chemistry 55 3-4 2006 279 287 (Pubitemid 44127266)
4. H. Boudad, P. Legrand, G. Lebas, M. Cheron, D. Duchene, and G. Ponchel Combined hydroxypropyl-beta-cyclodextrin and poly(alkylcyanoacrylate) nanoparticles intended for oral administration of saquinavir International Journal of Pharmaceutics 218 1-2 2001 113 124 (Pubitemid 32406162)
5. M.E. Brewster, and T. Loftsson Cyclodextrins as pharmaceutical solubilizers Advanced Drug Delivery Reviews 59 7 2007 645 666 (Pubitemid 47299263)
6. 2+ handling in A7r5 vascular myocytes European Journal of Pharmacology 577 1-3 2007 91 99 (Pubitemid 350001288)
7. M. Careri, C. Corradini, L. Elviri, I. Nicoletti, and I. Zagnoni Direct HPLC analysis of quercetin and trans-resveratrol in red wine, grape, and winemaking byproducts Journal of Agriculture and Food Chemistry 51 18 2003 5226 5231
8. R. Challa, A. Ahuja, J. Ali, and R.K. Khar Cyclodextrins in drug delivery: an updated review AAPS Pharmacy of Science and Technology 6 2 2005 E329 357
9. H.S. Courtney, W.A. Simpson, and E.H. Beachey Relationship of critical micelle concentrations of bacterial lipoteichoic acids to biological activities Infection and Immunity 51 2 1986 414 418 (Pubitemid 16212114)
10. A. Dahan, J.M. Miller, A. Hoffman, G.E. Amidon, and G.L. Amidon The solubility-permeability interplay in using cyclodextrins as pharmaceutical solubilizers: mechanistic modeling and application to progesterone Journal of Pharmaceutical Sciences 99 6 2010 2739 2749
11. F. Dai, W.F. Chen, and B. Zhou Antioxidant synergism of green tea polyphenols with alpha-tocopherol and L-ascorbic acid in SDS micelles Biochimie 90 10 2008 1499 1505
12. S. Das, H.S. Lin, P.C. Ho, and K.Y. Ng The impact of aqueous solubility and dose on the pharmacokinetic profiles of resveratrol Pharmaceutical Research 25 11 2008 2593 2600
13. E.M.M. Del Valle Cyclodextrins and their uses: a review Process Biochemistry 39 9 2004 1033 1046 (Pubitemid 38527174)
14. C. Dugave, and L. Demange Cis-trans isomerization of organic molecules and biomolecules: implications and applications Chemical Reviews 103 7 2003 2475 2532
15. C.M. Fernandes, R.A. Carvalho, S. Pereira da Costa, and F.J. Veiga Multimodal molecular encapsulation of nicardipine hydrochloride by beta-cyclodextrin, hydroxypropyl-beta-cyclodextrin and triacetyl-beta- cyclodextrin in solution. Structural studies by 1H NMR and ROESY experiments European Journal of Pharmaceutical Sciences 18 5 2003 285 296 (Pubitemid 36407688)
16. C.M. Fernandes, M. Teresa Vieira, and F.J. Veiga Physicochemical characterization and in vitro dissolution behavior of nicardipine-cyclodextrins inclusion compounds European Journal of Pharmaceutical Sciences 15 1 2002 79 88 (Pubitemid 34136971)
17. A. Figueiras, R.A. Carvalho, L. Ribeiro, J.J. Torres-Labandeira, and F.J. Veiga Solid-state characterization and dissolution profiles of the inclusion complexes of omeprazole with native and chemically modified beta-cyclodextrin European Journal of Pharmaceutics and Biopharmaceutics 67 2 2007 531 539 (Pubitemid 47211912)
18. U.S. Department of Health and Human Services, Food and Drug Administration. Guidance for Industry: Bioanalytical Method Validation. 2001.
19. S. Gokturk, E. Caliskan, R.Y. Talman, and U. Var A study on solubilization of poorly soluble drugs by cyclodextrins and micelles: complexation and binding characteristics of sulfamethoxazole and trimethoprim ScientificWorldJournal 2012 2012 718791
20. International Conference on Harmonization (ICH). Validation of Analytical Procedures: Methodology ICH Q2B. 2005.
21. T. Higuchi, and K.A. Connors Phase-solubility techniques Advances in Analytical Chemistry and Instrumentation 4 1965 117 212
22. T. Irie, and K. Uekama Pharmaceutical applications of cyclodextrins. III. Toxicological issues and safety evaluation Journal of Pharmaceutical Sciences 86 2 1997 147 162 (Pubitemid 27078377)
23. M.E. Juan, M. Maijo, and J.M. Planas Quantification of trans-resveratrol and its metabolites in rat plasma and tissues by HPLC Journal of Pharmaceutical and Biomedical Analysis 51 2 2010 391 398
24. Karoyo, A. H., Sidhu, P. S., Wilson, L., & Hazendonk, P. (2013). Characterization and dynamic properties for the solid inclusion complexes of beta-cyclodextrin and perfluorooctanoic acid. Journal of Physcis and Chemistry B, (in press).
25. Kasiotis, K. M., Pratsinis, H., Kletsas, D., & Haroutounian, S. A. (2013). Resveratrol and related stilbenes: Their anti-aging and anti-angiogenic properties. Food Chemical Toxicology, (in press).
26. J.L. Koontz, R.D. Moffitt, J.E. Marcy, S.F. O'Keefe, S.E. Duncan, and T.E. Long Controlled release of alpha-tocopherol, quercetin, and their cyclodextrin inclusion complexes from linear low-density polyethylene (LLDPE) films into a coconut oil model food system Food Additives and Contaminants Part A, Chemistry, Analysis, Control, Exposure and Risk Assessment 27 11 2010 1598 1607
27. S.K. Lee, H.J. Lee, H.Y. Min, E.J. Park, K.M. Lee, and Y.H. Ahn Antibacterial and antifungal activity of pinosylvin, a constituent of pine Fitoterapia 76 2 2005 258 260 (Pubitemid 40326981)
28. H.S. Lin, B.D. Yue, and P.C. Ho Determination of pterostilbene in rat plasma by a simple HPLC-UV method and its application in pre-clinical pharmacokinetic study Biomedical Chromatography 23 12 2009 1308 1315
29. J.M. Lopez-Nicolas, P. Rodriguez-Bonilla, and F. Garcia-Carmona Complexation of pinosylvin, an analogue of resveratrol with high antifungal and antimicrobial activity, by different types of cyclodextrins Journal of Agriculture and Food Chemistry 57 21 2009 10175 10180
30. J.M. Lopez-Nicolas, P. Rodriguez-Bonilla, L. Mendez-Cazorla, and F. Garcia-Carmona Physicochemical study of the complexation of pterostilbene by natural and modified cyclodextrins Journal of Agriculture and Food Chemistry 57 12 2009 5294 5300
31. Z. Lu, B. Cheng, Y.L. Hu, Y.H. Zhang, and G.L. Zou Complexation of resveratrol with cyclodextrins: Solubility and antioxidant activity Food Chemistry 113 1 2009 17 20
32. T. Macickova, K. Drabikova, R. Nosal, K. Bauerova, D. Mihalova, and J. Harmatha In vivo effect of pinosylvin and pterostilbene in the animal model of adjuvant arthritis Neuroendocrinology Letters 31 Suppl 2 2010 91 95
33. K. Matsuoka, and Y. Moroi Micelle formation of sodium deoxycholate and sodium ursodeoxycholate (part 1) Biochimica et Biophysica Acta 1580 2-3 2002 189 199 (Pubitemid 34203873)
34. C.Y. Panickera, H.T. Varghese, K.R. Ambujakshan, S. Mathew, S. Ganguli, and A.K. Nandag Ab initio and density functional theory studies on vibrational spectra of 3-{[(4-methoxyphenyl)methylene]amino-2-phenylquinazolin-4(3H)-one European Journal of Chemistry 1 1 2010 37 43
35. E.J. Park, H.J. Park, H.J. Chung, Y. Shin, H.Y. Min, and J.Y. Hong Antimetastatic activity of pinosylvin, a natural stilbenoid, is associated with the suppression of matrix metalloproteinases Journal of Nutritional Biochemistry 23 8 2012 946 952
36. L. Paulo, F. Domingues, J.A. Queiroz, and E. Gallardo Development and validation of an analytical method for the determination of trans- and cis- resveratrol in wine: Analysis of its contents in 186 portuguese wines Journal of Agriculture and Food Chemistry 59 6 2011 2157 2168
37. L. Paulo, S. Ferreira, E. Gallardo, J.A. Queiroz, and F. Domingues Antimicrobial activity and effects of resveratrol on human pathogenic bacteria World Journal of Microbiology & Biotechnology 26 8 2010 1533 1538
38. M. Posa, V. Guzsvany, and J. Csanadi Determination of critical micellar concentrations of two monoketo derivatives of cholic acid Colloids Surface B Biointerfaces 74 1 2009 84 90
39. 1H NMR determination of the critical micellar concentrations of two oxo-derivatives of cholic acid. Which of the two is more hydrophobic? Sensor Electroanalytical 5 2010 195 208
40. S. Reis, C.G. Moutinho, C. Matos, B. de Castro, P. Gameiro, and J.L. Lima Noninvasive methods to determine the critical micelle concentration of some bile acid salts Analytical Biochemistry 334 1 2004 117 126 (Pubitemid 39304082)
41. A. Ribeiro, A. Figueiras, D. Santos, and F. Veiga Preparation and solid-state characterization of inclusion complexes formed between miconazole and methyl-beta-cyclodextrin AAPS Pharmacy of Science and Techonolgy 9 4 2008 1102 1109
42. C. Rius, M. Abu-Taha, C. Hermenegildo, L. Piqueras, J.M. Cerda-Nicolas, and A.C. Issekutz Trans- but not cis-resveratrol impairs angiotensin-II-mediated vascular inflammation through inhibition of NF-kappaB activation and peroxisome proliferator-activated receptor-gamma upregulation Journal of Immunology 185 6 2010 3718 3727
43. C. Riviere, A.D. Pawlus, and J.M. Merillon Natural stilbenoids: distribution in the plant kingdom and chemotaxonomic interest in Vitaceae Natural Products Reports 29 11 2012 1317 1333
44. A. Roda, A.F. Hofmann, and K.J. Mysels The influence of bile salt structure on self-association in aqueous solutions Journal of Biological Chemistry 258 10 1983 6362 6370 (Pubitemid 13106811)
45. K. Roupe, S. Halls, and N.M. Davies Determination and assay validation of pinosylvin in rat serum: application to drug metabolism and pharmacokinetics Journal of Pharmaceutical and Biomedical Analysis 38 1 2005 148 154 (Pubitemid 40725101)
46. T. Shen, X.N. Wang, and H.X. Lou Natural stilbenes: an overview Natural Products Reports 26 7 2009 916 935
47. B.R. Simonovic, and M. Momirovic Determination of critical micelle concentration of bile acid salts by micro-calorimetric titration Mikrochimica Acta 127 1-2 1997 101 104 (Pubitemid 127474784)
48. L.H. Tong Cyclodextrin chemistry - theory and application 2001 The Science Press Beijing
49. P. Waffo-Teguo, M.E. Hawthorne, M. Cuendet, J.M. Merillon, A.D. Kinghorn, and J.M. Pezzuto Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures Nutrition and Cancer 40 2 2001 173 179 (Pubitemid 34274924)
50. R.O. Williams 3rd, V. Mahaguna, and M. Sriwongjanya Characterization of an inclusion complex of cholesterol and hydroxypropyl-beta-cyclodextrin European Journal of Pharmaceutics and Biopharmaceutics 46 3 1998 355 360 (Pubitemid 29057684)