Beta-cyclodextrin complexes with chlorogenic and caffeic acids from coffee brew: Spectroscopic, thermodynamic and molecular modelling study

Food Chemistry

Volumn 114, Issue 1, 2009, Pages 190-196

  Górnas, Paweł ^a   Neunert, Grazyna ^a   Baczyński, Krzysztof ^b   Polewski, Krzysztof ^a  

^a POZNA UNIVERSITY OF LIFE SCIENCES   (Poland)

^b JAGIELLONIAN UNIVERSITY   (Poland)

Author keywords

Beta cyclodextrin; Brewed coffee; Caffeic acid; Chlorogenic acid; Fluorescence; Inclusion complex; Molecular modeling; Thermodynamic parameters

Indexed keywords

EID: 58149489026     PISSN: 03088146     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodchem.2008.09.048     Document Type: Article

References (28)

1. Agostiano A., Catucci L., Cosma P., and Fini P. Aggregation processes and photophysical properties of chlorophyll a in aqueous solutions modulated by the presence of cyclodextrins. Physical Chemistry Chemical Physics 5 (2003) 2122-2128
2. Anderson T.G., Tan A., Ganz P., and Seelig J. Calorimetric measurement of phospholipid interaction with methyl-beta-cyclodextrin. Biochemistry 43 (2004) 2251-2261
3. In: Bender M.L., and Komiyama M. (Eds). Cyclodextrin chemistry (1978), Springer-Verlag, Berlin
4. Baglole K.N., Boland P.G., and Wagner B.D. Fluorescence enhancement of curcumin upon inclusion into parent and modified cyclodextrins. Journal of Photochemistry and Photobiology A 173 (2005) 230-237
5. Berendsen H.J.C., Postma J.P.M., van Gunsteren W.F., and Hermans J. Intermolecular forces (1981), Reidel, Dordrecht
6. Berendsen H.J.C., van der Spoel D., and van Drunen R. GROMACS: A message-passing parallel molecular dynamics implementation. Computer Physics Communications 91 (1995) 43-56
7. Bicchi C.P., Binello A.E., Pellegrino G.M., and Vianni A.C. Characterization of roasted coffee and coffee beverages by solid phase microextraction-gas chromatography and principal component analysis. Journal of Agricultural and Food Chemistry 43 (1995) 1549-1555
8. Clifford M.N. Diet-derived phenols in plasma and tissues and their implications for health. Planta Medica 70 (2004) 1103-1114
9. Cosma P., Catucci L., Fini P., Dentuto P.L., Agostiano A., Angelini N., et al. Tetrakis(4-pyridyl)porphyrin supramolecular complexes with cyclodextrins in aqueous solution. Journal of Photochemistry and Photobiology 82 (2006) 563-569
10. Daura X., Mark A.E., and van Gunsteren W.F. Parametrisation of aliphatic CHn united atoms of GROMOS96 force field. Journal of Computational Chemistry 19 (1998) 535-547
11. Del Valle M.E.M. Cyclodextrins and their uses: A review. Process Biochemistry 39 (2004) 1033-1046
12. DeLano W.L. The PyMOL molecular graphics system (2002), DeLano Scientific, Palo Alto, CA, USA
13. Divakar S., and Maheswaran M.M. Structural studies on inclusion compounds of beta-cyclodextrin with some substituted phenols. Journal of Inclusion Phenomena and Molecular Recognition in Chemistry 27 (1997) 113-126
14. Fini P., Longobardi F., Catucci L., Cosma P., and Agostiano A. Spectroscopic and electrochemical study of Rose Bengal in aqueous solutions of cyclodextrins. Bioelectrochemistry 63 (2004) 107-110
15. Fini P., Loseto R., Catucci L., Cosma P., and Agostiano A. Study on the aggregation and electrochemical properties of Rose Bengal in aqueous solution of cyclodextrins. Bioelectrochemistry 70 (2007) 44-49
16. Hashimoto H. CyD applications in food, cosmetic, toiletry, textile and wrapping material fields Cyclodextrins and Their Complexes. In: Dodziuk H. (Ed) (2006), Wiley-VCH Verlag GmbH & Co, KGaA, Weinheim 452-458
17. Irwin P., Brouillette J., Giampa A., Hicks K., Gehring A., and Tu S.-I. Cyclomaltoheptaose (beta-cyclodextrin) inclusion complex formation with chlorogenic acid: hydration enthalpy, the solvent entropy (hydrophoboc effect), and enthalpy-entropy compensation. Carbohydrate Research 332 (1999) 67-76
18. Lindahl E., Hess B., and van der Spoel D. GROMACS 3.0: A package for molecular simulation and trajectory analysis. Journal of Molecular Modeling 7 (2001) 306-317
19. pdb1dmb.ent: .
20. Rodrigues E., Vaz S., Gil V.M.S.S., Caldeira M.M., and da Silva M.A.M.G. Inclusion of polyphenol oxidase substrates in β-cyclodextrin: A 1H-NMR study. Journal of Inclusion Phenomena and Macrocyclic Chemistry 44 (2002) 395-397
21. Schuettelkopf A.W., and van Aalten D.M.F. PRODRG-A tool for high-throughput crystallography of protein-ligand complexes. Acta Crystallographica D 60 (2004) 1355-1363
22. Singh M., and Sharma R. Biotechnological applications of cyclodextrins. Biotechnology Advances 20 (2002) 341-359
23. Szejtli J., and Szente L. Elimination of bitter, disgusting tastes of drugs and foods by cyclodextrins. European Journal of Pharmaceutics and Biopharmaceutics 61 (2005) 115-125
24. Szente L., and Szejtli J. Cyclodextrins as food ingrediens. Trends in Food Science and Technology 15 (2004) 137-142
25. Tanhuanpaa K., Cheng K.H., Anttonen K., Virtanen J.A., and Somerharju P. Characteristics of pyrene phospholipid/gamma-cyclodextrin complex. Biophysical Journal 81 (2001) 1501-1510
26. Van Gunsteren, W.F., Billeter, S.R., Eising, A.A., Hunenberger, P.H., Kruger, P., Mark, A.E., et al. (1996). Biomolecular simulation: Gromos96 manual and user guide. Zurich, Groningen, Biomos b.v.
27. Verrone R., Catucci L., Cosma P., Fini P., Agostiano A., Lippolis V., et al. Effect of beta-cyclodextrin on spectroscopic properties of ochratoxin A in aqueous solution. Journal of Inclusion Phenomena and Macrocyclic Chemistry 57 (2007) 475-479
28. Wagner B.D., and MacDonald P.J. The fluorescence enhancement of 1-anilinonaphthalene-8-sulfonate (ANS) by modified b-cyclodextrins. Journal of Photochemistry and Photobiology A 114 (1998) 151-157