Advertisement

Complexation of Apple Antioxidants: Chlorogenic Acid, Quercetin and Rutin by β-Cyclodextrin (β-CD)

  • Emilio Alvarez-Parrilla
  • Laura A. De La Rosa
  • Francisco Torres-Rivas
  • Joaquín Rodrigo-Garcia
  • Gustavo A. González-Aguilar
Article

Abstract

The complexation and antioxidant activity of the major apple polyphenols: Chlorogenic Acid (CA), Rutin (Rt) and Quercetin (Qc) with β-cyclodextrin (β-CD) were studied, by fluorescence spectroscopy and Ferric Reducing/Antioxidant Power Assay (FRAP) techniques. All polyphenols formed 1:1 stoichiometry complexes. Their stability constants decreased in the order Qc (1138 M−1) > CA (465 M−1) > Rt (224 M−1). The complex formation was also confirmed in the solid state by DSC measurements. Qc showed the highest antioxidant activity, followed by Rt and CA. In all cases, the complexation process produced a slight increment in their antioxidant activity (between 7 and 14%), more evident for Rt and CA than for Qc.

Keywords

antioxidant capacity β-cyclodextrin fluorescence spectroscopy food antioxidants FRAP inclusion complexes polyphenols 

Abbreviations

CA

chlorogenic acid

CD

cyclodextrin

β-CD

β-cyclodextrin

FRAP

Ferric reducing antioxidant power

HSA

Human Serum Albumin

λem

emission wavelength

λexc

excitation wavelength

Qc

quercetin

Rt

rutin

TPTZ

2,4,6-tripyridyl-s-triazine

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Hertog, MG., Kromhout, D., Aravanis, C., Blackburn, H., Buzina, R., Filanza, F., Giampaoli, S., Jansen, A., Menotti, A., Nedeljkovic, S. 1995Arch. Intern. Med.155381CrossRefPubMedGoogle Scholar
  2. 2.
    Vinson, JA., Su, X., Zubik, L., Bose, P. 2001J. Agric. Food Chem.495315CrossRefPubMedGoogle Scholar
  3. 3.
    Eberhardt, MV., Lee, CY., Liu, R.H. 2000Nature405903Google Scholar
  4. 4.
    Wolfe, K., Wu, X., Liu, R.H. 2003J. Agric. Food Chem.51609CrossRefPubMedGoogle Scholar
  5. 5.
    Coseteng, W.Y., Lee, C.Y. 1987J. Food Sci52985Google Scholar
  6. 6.
    Sapers, GM., Hicks, K., Phillips, JG., Garzarella, L., Pondish, DL., Matulaitis, RM., McCormack, TJ., Sondey, SM., Seib, PA., El-Atawy, Y.S. 1989J. Food Sci.54997Google Scholar
  7. 7.
    Monsalve-González, A., Barbosa-Canovas, G.V, McEvily, AJ., Iyengar, R. 1995Food Technol.4110Google Scholar
  8. 8.
    Fayad, N., Marchal, L., Billaud, C., Nicolas, J. 1997J. Agr. Food Chem.452442CrossRefGoogle Scholar
  9. 9.
    Özoglu, H., Bayindirli, A. 2002Food Control13213Google Scholar
  10. 10.
    Lezcano, M., Al-Soufi, W., Novo, M., Rodríguez-Núñez, E., Vázquez Tato, J 2002J. Agr. Food Chem.50108CrossRefGoogle Scholar
  11. 11.
    Mar Sojo, M., Nuñez-Delicado, E., García-Carmona, F., Sánchez-Ferrer, A 1999J. Agr. Food Chem.47518CrossRefGoogle Scholar
  12. 12.
    Irwin, P., Pfeffer, PE., Doner, LW., Sapers, GM., Brewster, JD., Nagahashi, G., Hicks, K. 1994Carbohydr. Res.25613CrossRefPubMedGoogle Scholar
  13. 13.
    Irwin, P., Brouillette, J., Hicks, K. 1995Carbohydr. Res.269201CrossRefGoogle Scholar
  14. 14.
    Letellier, S., Maupas, B., Gramond, JP., Guyon, F., Gareil, P. 1995Anal. Chim. Acta315357CrossRefGoogle Scholar
  15. 15.
    Irwin, P., King, G., Hicks, K. 1996Carbohydr. Res.28265CrossRefPubMedGoogle Scholar
  16. 16.
    Lederer, M., Leipzing-Pagani, E. 1996Anal. Chim. Acta329311CrossRefGoogle Scholar
  17. 17.
    Irwin, P., Brouillette, J., Giampa, A., Hicks, K., Gehring, A., Tu, A.-I. 1999Carbohydr. Res.32267CrossRefGoogle Scholar
  18. 18.
    Ishizu, T., Kintsu, K., Yamamoto, H. 1999J. Phys. Chem. B.1038992CrossRefGoogle Scholar
  19. 19.
    Miyake, K., Arima, H., Hirayama, F., Yamamoto, M., Horikawa, T., Sumiyoshi, H., Noda, S., Ueka, K. 2000Pharm. Dev. Tech.5399CrossRefGoogle Scholar
  20. 20.
    Rodrigues, E., Vaz, S., Gil, V.M.S.S., Caldeira, MM., Moreirada Silva, A.M.G. 2002J. Incl. Phenom. Macrocycl. Chem.44395CrossRefGoogle Scholar
  21. 21.
    Haiyun, D., Jianbin, Z., Guomei, Z., Shaomin, S., Jinhao, P. 2003Spectrochim. Acta A.593421Google Scholar
  22. 22.
    Pralhad, T., Rajendrakumar, K. 2004J. Pharm. Biomed. Anal.34333CrossRefPubMedGoogle Scholar
  23. 23.
    Alvarez-Parrilla, E., Al-Soufi, W., Ramos Cabrer, P., Novo, M., Vázquez Tato, J. 2001J. Phys. Chem. B.1055994CrossRefGoogle Scholar
  24. 24.
    Connors, K.A. 1987Binding Constants: The Measurement of Molecular Complex StabilityJohn Wiley and Sons, Inc.USAGoogle Scholar
  25. 25.
    Benzie, I.F.F., Strain, J.J. 1996Anal. Biochem.23970CrossRefPubMedGoogle Scholar
  26. 26.
    Pulido, R., Bravo, L., Saura-Calixto, F. 2000J. Agr. Food Chem.483396CrossRefGoogle Scholar
  27. 27.
    Al-Hassan, K.A., Khanfer, M.F. 1998J. Fluoresc8139CrossRefGoogle Scholar
  28. 28.
    Indirapriyadharshini, VK., Karunanithi, P., Ramamurthy, P. 2001Langmuir174056Google Scholar
  29. 29.
    Zhu, L., Qi, Z., Lu, Z., Jing, H., Qi, W. 1996Microchem. J.53361CrossRefGoogle Scholar
  30. 30.
    Falkovskaia, E., Sengupta, PK., Kasha, M. 1998Chem. Phys. Lett.297109CrossRefGoogle Scholar
  31. 31.
    Sengupta, B., Sengupta, P.K. 2002Biochem. Biophys. Res. Commun.199400CrossRefGoogle Scholar
  32. 32.
    García-Campaña, A.M., Alés Barrero, F., Lupiáñez Gonzalez, A., Román Ceba, M. 2001Anal. Chim. Acta447219CrossRefGoogle Scholar
  33. 33.
    Gutierrez, A.C., Gehlen, M.H. 2002Spectrochim Acta A5883Google Scholar
  34. 34.
    Gupta, K., Panda, D. 2003Biochemistry4113029CrossRefGoogle Scholar
  35. 35.
    Lezcano M. (2002). Ph.D. thesis. Universidad de Santiago de Compostela, SpainGoogle Scholar
  36. 36.
    Nagase, Y., Suzuki, N., Yamauchi, H., Kim, S., Wada, K., Arima, H., Hirayama, F., Uekama, K. 2002J. Incl. Phenom. Macrocycl. Chem.44107CrossRefGoogle Scholar
  37. 37.
    Huang, D., Ou, B., Hampsch-Woodill, M., Flanagan, JA., Deemer, E.K. 2002J. Agr. Food Chem.501815CrossRefGoogle Scholar
  38. 38.
    Ou, B., Huang, D., Hampsch-Woodill, M., Flanagan, JA., Deemer, E.K. 2002J. Agr. Food Chem.503122CrossRefGoogle Scholar
  39. 39.
    Mayer, B., Schumacher, M., Brandstätter, H., Wagner, F.S. 2001Anal. Biochem.297144CrossRefPubMedGoogle Scholar
  40. 40.
    Isao, A., Kikujiro, U., Hidondo, K. 2001Bull. Chem. Soc. Jpn.74717CrossRefGoogle Scholar

Copyright information

© Springer 2005

Authors and Affiliations

  • Emilio Alvarez-Parrilla
    • 1
  • Laura A. De La Rosa
    • 1
  • Francisco Torres-Rivas
    • 1
  • Joaquín Rodrigo-Garcia
    • 1
  • Gustavo A. González-Aguilar
    • 2
  1. 1.Departamento de Ciencias Básicas, Instituto de Ciencias BiomédicasUniversidad Autónoma de Ciudad JuárezChihuahuaMéxico
  2. 2.Centro de Investigación en Alimentación y DesarrolloA. C. (CIAD, A. C.) Dirección de Tecnología de Alimentos de Origen VegetalHermosilloMéxico

Personalised recommendations