Artículo

Estamos trabajando para incorporar este artículo al repositorio
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

Background: Cyclodextrins (CDs) are able to enhance the solubility, stability and bioavailability of several bioactive hydrophobic compounds by complex formation. They can also be used for removal of undesired components (such as cholesterol, off-flavors or bitter components) present in foods. Although many patents account for the use of cyclodextrins for removal of cholesterol from dairy foods, there is no available information on the effect of water on encapsulation efficiency and on the stability of sterols in CDs. The aim of this work was to study the inclusion properties and the factors affecting the encapsulation and stability of cholesterol in β-cyclodextrin (BCD). The optimum encapsulation conditions (ligand-CD molar ratio, stirring time and temperature), and stability of the complexes as a function of storage time and water content were analyzed. Results: Phase solubility study pointed out the formation of 1:1 stoichiometric complexes between cholesterol and β-cyclodextrin, which was influenced by temperature variations. The process was shown to be exothermic and energetically favored. The presence of cholesterol greatly modified the BCD water sorption curves, being the amount of adsorbed water smaller in the combined systems. The principal 'driving force' for complex formation is the substitution of the high-enthalpy water molecules by an appropriate hydrophobic ligand. The freeze-dried complexes probed to be stable at different storage conditions. Conclusion: The phase solubility and stability data obtained could be essential for selecting the most suitable conditions when CDs are employed either for removing cholesterol or to incorporate functional ingredients (i.e. sitosterol) in the development of innovative food products. © 2011 Society of Chemical Industry.

Registro:

Documento: Artículo
Título:Phase solubility studies and stability of cholesterol/β-cyclodextrin inclusion complexes
Autor:dos Santos, C.; Buera, M.P.; Mazzobre, M.F.
Filiación:Departamento de Industrias, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Intendente Güiraldes 2160 Cid. Universitaria C1428EGA, Buenos Aires, Argentina
Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Intendente Güiraldes 2160 Cid. Universitaria C1428EGA, Buenos Aires, Argentina
Palabras clave:Cholesterol; Cyclodextrin; Phase solubility; Stability constants; beta cyclodextrin derivative; cholesterol; coordination compound; food additive; ligand; phytosterol; water; adsorption; article; chemical phenomena; chemistry; diet supplementation; differential scanning calorimetry; food handling; freeze drying; heat; kinetics; phase transition; solubility; Adsorption; beta-Cyclodextrins; Calorimetry, Differential Scanning; Cholesterol; Coordination Complexes; Food Additives; Food Handling; Food, Fortified; Freeze Drying; Hot Temperature; Hydrophobic and Hydrophilic Interactions; Kinetics; Ligands; Phase Transition; Phytosterols; Solubility; Water
Año:2011
Volumen:91
Número:14
Página de inicio:2551
Página de fin:2557
DOI: http://dx.doi.org/10.1002/jsfa.4425
Título revista:Journal of the Science of Food and Agriculture
Título revista abreviado:J. Sci. Food Agric.
ISSN:00225142
CODEN:JSFAA
CAS:cholesterol, 57-88-5; water, 7732-18-5; Cholesterol, 57-88-5; Coordination Complexes; Food Additives; Ligands; Phytosterols; Water, 7732-18-5; beta-Cyclodextrins
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00225142_v91_n14_p2551_dosSantos

Referencias:

  • Young, Y., Functional foods and the European consumer (2000) Functional Foods. II. Claims and Evidence, , ed. by Buttriss J and Saltmarsh M. The Royal Society of Chemistry, London
  • Roberfroid, M.B., A European consensus of scientific concepts of functional foods (2000) Nutrition, 16, pp. 689-691
  • Mollet, B., Rowland, I., Functional foods: At the frontier between food and pharma (2002) Curr Opin Biotechnol, 13, pp. 483-485
  • Menrad, K., Market and marketing of functional food in Europe (2003) J Food Eng, 56, pp. 181-188
  • Schroder, B.G., Baer, R.J., Utilization of cholesterol reduced milk fat in fluid milks (1990) Food Technol, pp. 145-148
  • Durkley, W.L., Reducing fat in milk and dairy products by processing (1982) J Dairy Sci, 65, pp. 454-458
  • Larsen, J.E., Froning, G.W., Extraction and processing of various components from egg yolk (1981) J Poult Sci, 60, pp. 160-167
  • Watanabe, K.H., Aihara, H., Nakamura, R., Properties of the purified extracellular cholesterol oxidase from Rhodococcus Equi (1989) J Agric Food Chem, 37, pp. 1178-1182
  • Ong, D.P., Lee, H.K., Li, S.F.Y., Supercritical fluid extraction and chromatography of cholesterol in food sample (1990) J Chromatogr, 515, pp. 509-513
  • Brewster, M.E., Loftsson, T., Cyclodextrins as pharmaceutical solubilizers (2007) Adv Drug Delivery Rev, 59, pp. 645-666
  • Hedges, A.R., Industrial applications of cyclodextrins (1998) Chem Rev, 98, pp. 2035-2044
  • Calabró, M.L., Tommasini, S., Donato, P., Stancanelli, R., Ficarra, P., Ficarra, R., Effects of α- and β-cyclodextrin complexation on the physico-chemical properties and antioxidant activity of some 3-hydroxyflavones (2004) J Pharm Biomed Anal, 35, pp. 365-377
  • Lucas-Abellán, C., Fortea, M.I., López-Nicolás, J.M., Núñez-Delicado, E., Cyclodextrins as resveratrol carrier system (2007) Food Chem, 104, pp. 39-44
  • Tommasini, S., Raneri, D., Ficarra, R., Calabró, M.L., Stancanelli, R., Ficarra, P., Improvement in solubility and dissolution rate of flavonoids by complexation with β-cyclodextrin (2004) J Pharm Biomed Anal, 35, pp. 379-387
  • Polyakov, N., Leshina, T., Konovalova, T., Hand, E., Kispert, L., Inclusion complexes of carotenoids with cyclodextrins: 1H-NMR, EPR and optical studies (2004) Free Radic Biol Med, 36, pp. 872-880
  • Szente, L., Szejtli, J., Cyclodextrins as food ingredients (2004) Trends Food Sci Technol, 15, pp. 137-142
  • Karathanos, V.T., Mourtzinos, K., Yannakopolou, K., Andrikopoulos, N.K., Study of the solubility, antioxidant activity and structure of inclusion complex of vanillin with β-cyclodextrin (2007) Food Chem, 101, pp. 652-658
  • Oakenfull, D.G., Sihdu, G.S., Cholesterol reduction (1991) Int Patent, pp. 91/11114
  • Makoto, K., Akio, O., Reijiro, S., Cholesterol removal from animal with cyclodextrin by inclusion (1992) Jpn Patent, 4, pp. 168-198
  • Ahn, J., Kwak, H.S., Optimizing cholesterol removal in cream using β-cyclodextrin and response surface methodology (1999) J Food Sci, 64, pp. 629-632
  • Lee, D.K., Ahn, J., Kwak, H.S., Cholesterol removal from homogenized milk with β-cyclodextrin (1999) J Dairy Sci, 82, pp. 2327-2330
  • Kwak, H.S., Suh, H.M., Ahn, J., Kwon, H.J., Optimization of β-cyclodextrin recycling process for cholesterol removal in cream (2001) Asian-Aust J Anim Sci, 14, pp. 548-552
  • Nagamoto, S., Cyclodextrin-expanding the development of their functions and applications (1985) Chem Ecol Eng Rev, 17, pp. 28-34
  • Kwak, H.S., Chung, C.S., Ahn, J., Flavor compounds of cholesterol-reduced Cheddar cheese slurries (2002) Asian-Aust J Anim Sci, 15, pp. 117-123
  • Astray, G., Mejuto, J.C., Rial-Otero, R., Gonzalez-Barreiro, C., Simal-Gándara, J.A., A review on the use of cyclodextrins in foods (2009) Food Hydrocol, 23, pp. 1631-1640
  • Higuchi, T., Connors, K., Phase-solubility techniques (1965) Adv Anal Chem Instrument, 4, pp. 117-120
  • Williams, R.O., Mahaguna, V., Sriwongjanya, M., Characterization of an inclusion complex of cholesterol and hydroxypropyl-bcyclodextrin (1998) Eur J Pharm Biopharm, 46, pp. 355-360
  • Greenspan, L., Humidity fixed points of binary saturated aqueous solutions (1977) J Res Natl Bur Stand, Sect A, 81, pp. 89-96
  • Frijlink, H.W., Eissens, A.C., Hefting, N.R., Poelstra, K., Lerk, C.F., Meijer, D.K.F., The effect of parenterally administered cyclodextrins on cholesterol levels in the rat (1991) Pharm Res, 8, pp. 9-16
  • Rekharsky, M.V., Inoue, Y., Complexation thermodynamics of cyclodextrins (1998) Chem Rev, 98, pp. 1875-1917
  • Hoshino, T., Uekama, K., Pitha, J., Increase in temperature enhances solubility of drugs in aqueous solutions of hydroxypropylcyclodextrins (1993) Int J Pharm, 98, pp. 239-242
  • Mourtzinos, I., Kalogeropoulos, N., Papadakis, S.E., Konstantinou, K., Karathanos, V.T., Encapsulation of nutraceutical monoterpenes in β-cyclodextrin and modified starch (2008) J Food Sci, 73, pp. 89-94
  • Mazzobre, M.F., dos Santos, C., Buera, M.P., Solubility and Stability of β-Cyclodextrin-Terpineol Inclusion Complex as Affected by Water (2011) Food Biophys, , In press
  • Pralhad, T., Rajendrakumar, K., Study of freeze-dried quercetin-cyclodextrin binary systems by DSC, FT-IR, X-ray diffraction and SEM analysis (2004) J Pharm Biomed Anal, 34, pp. 333-339
  • dos Santos, C., Mazzobre, M.F., Elizalde, B., Buera, M.P., Influencia de modificaciones de beta-ciclodextrina sobre su interacción con el agua y ligandos de distinta estructura (2007) Alimentos Ciencia e Ingeniería de alimentos, 16, pp. 71-73
  • Ponce-Cevallos, P.A., Buera, M.P., Elizalde, B.E., Water sorption and thermal properties of β-cyclodextrin and methyl-β-cyclodextrin and their inclusion complexes with thymol and cinnamaldehyde (2010) J Food Eng, 99, pp. 70-75
  • Winkler, R.G., Fioravanti, S., Ciccotti, G., Margheritis, C., Villa, M., Hydration of β-cyclodextrin: A molecular dynamics simulation study (2000) J Comput Aided Mol Des, 14, pp. 659-667
  • Timmermman, E.O., Chirife, J., The physical state of water sorbed at high activities in starch in terms of the GAB sorption equation (1991) J Food Eng, 3, pp. 171-179
  • Mazzobre, M.F., Elizalde, B., dos Santos, C., Ponce Cevallos, P., Buera, M.P., Nanoencapsulation of food ingredients in cyclodextrins: Effect of water interactions and ligand structure (2010) Functional Food Product Development. Part I: New Technologies for Functional Food Manufacture, pp. 25-38. , ed. by Smith J and Charter E. Wiley Blackwell, Oxford -
  • Chen, P., Long, Z., Ruan, R., Labuza, T., Nuclear magnetic resonance studies of water mobility in bread during storage (1997) Lebensm-Wiss Technol, 30, pp. 178-183
  • Choi, S., Kerr, W., 1H NMR studies of molecular mobility in wheat starch (2003) Food Res Int, 36, pp. 341-348

Citas:

---------- APA ----------
dos Santos, C., Buera, M.P. & Mazzobre, M.F. (2011) . Phase solubility studies and stability of cholesterol/β-cyclodextrin inclusion complexes. Journal of the Science of Food and Agriculture, 91(14), 2551-2557.
http://dx.doi.org/10.1002/jsfa.4425
---------- CHICAGO ----------
dos Santos, C., Buera, M.P., Mazzobre, M.F. "Phase solubility studies and stability of cholesterol/β-cyclodextrin inclusion complexes" . Journal of the Science of Food and Agriculture 91, no. 14 (2011) : 2551-2557.
http://dx.doi.org/10.1002/jsfa.4425
---------- MLA ----------
dos Santos, C., Buera, M.P., Mazzobre, M.F. "Phase solubility studies and stability of cholesterol/β-cyclodextrin inclusion complexes" . Journal of the Science of Food and Agriculture, vol. 91, no. 14, 2011, pp. 2551-2557.
http://dx.doi.org/10.1002/jsfa.4425
---------- VANCOUVER ----------
dos Santos, C., Buera, M.P., Mazzobre, M.F. Phase solubility studies and stability of cholesterol/β-cyclodextrin inclusion complexes. J. Sci. Food Agric. 2011;91(14):2551-2557.
http://dx.doi.org/10.1002/jsfa.4425