Formation of Two 1:1 Chlorogenic Acid: β-cyclodextrin Complexes at pH 5: Spectroscopic, Thermodynamic and Voltammetric study †
DOI:
https://doi.org/10.29356/jmcs.v54i2.953Keywords:
b-cyclodextrin, chlorogenic acid, inclusion complexes, fluorescence, isothermal titration calorimetry (ITC), thermodynamic parametersAbstract
Complexation of chlorogenic acid (CA) by b-cyclodextrin (b-CD) at mildly acidic pH, was studied by fluorescence spectroscopy, isothermal titration calorimetry (ITC), cyclic voltammetry (CV) and NMR spectroscopy. Thermodynamic parameters (DH°, DS° and K) determined by both fluorescence and ITC, showed that the complexation of CA by b-CD is an enthalpy-driven process. Results show that CA molecule can be complexed through both polyphenolic and quinic acid moiety, leading to the formation of two supramolecular isomers with 1:1 stoichiometry.
Downloads
Download data is not yet available.
References
1. Alvarez-Parrilla, E.; de la Rosa, L. A.; Torres-Rivas, F.; RodrigoGarcía, J; González-Aguilar, G. A. J. Inclusion Phenom. Macrocycl. Chem. 2005, 53, 121-129.
2. Hertog, M. G.; Kromhout, D.; Aravanis, C.; Blackburn, H.; Buzina, R.; Filanza, F.; Giampaoli, S.; Cansen, A.; Menotti, A.; Nedeljkovic, S. Arch. Intern. Med. 1995, 155, 381-386.
3. Jullian, C.; Orosteguis, T.; Pérez-Cruz, F.; Sánchez, P.; Mendizábal, F.; Olea-Azar, C. Spectrochim. Acta A. 2008, 71, 269-275.
4. Mourtzinos, I.; Makris, D. P.; Yannakopoulou, K.; Kalogeropoulos, N.; Machali, I.; Karathanos, V. T. J. Agric. Food Chem. 2008, 56, 10303-10310.
5. Lucas-Abellán, C.; Fortea, I.; Gabaldón, J. A.; Núñez-Delicado, E. J. Agric. Food Chem. 2008, 56, 255-259.
6. López-Nicolas, J. M.; Garcia-Carmona, F. J. Agric. Food Chem. 2007, 55, 6330-6338.
7. López-Nicolas, J. M.; Pérez-López, A.; Carbonell-Barrachina, A.; Garcia-Carmona, F. J. Agric. Food Chem. 2007, 55, 5312-5319.
8. Alvarez-Parrilla, E.; de la Rosa, L.A.; Rodrigo-Garcia, J.; Escobedo-Gonzalez, R.; Mercado-Mercado, G.; Moyers-Montoya, E.; Vazquez-Flores, A.; Gonzalez-Aguilar, G.A. Food Chem. 2007, 101, 1346-1356.
9. Queiroz, C.; Mendes Lopes, M. L.; Fialho, E.; Valente-Mequita, V. L. Food Rev. Int. 2008, 24, 361-375.
10. Gacche, R. N.; Zore, G. B.; Ghole, V. S. J. Enz. Inh. Med. Chem. 2003, 18, 1-5.
11. Casado-Vela, J.; Selles, S.; Bru, R. J. Food Biochem. 2006, 30, 623-640.
12. Fayad, N.; Marchal, L.; Billaud, C.; Nicolas, J. J. Agric. Food Chem. 1997, 45, 2442-2446.
13. Górnas, P.; Neunert, G.; Baczyñski, K.; Polewski, K. Food Chem. 2009, 114, 190-196.
14. Rodrigues, E.; Vaz, S.; Gil, V. M. S. S.; Caldeira, M. M.; Moreira de Silva, A. M. G. J. Inclusion Phenom. Macroxyclic Chem. 2002, 44, 395–397.
15. Shuang, S.-M.; Pan, J-H.; Guo, S.-Y.; Cai, M.-Y.; Liu, C.-S. Anal. Lett. 1997, 30, 2261-2270.
16. Alvarez-Parrilla, E.; Al-Soufi, W.; Ramos Cabrer, P.; Novo, M.; Vázquez Tato, J. J. Phys. Chem. B. 2001, 105, 5994-6003.
17. de Bôer, G.; Hanson, F. E. Entomol. Exp. Appl. 1987, 45, 123131.
18. Namazian, M.; Zare, H. R. Electrochim. Acta. 2005, 50, 43504355.
19. Irwin, P.; Brouillette, J.; Giampa, A.; Hicks, K.; Gering, A.; Tu, S.-I. Carbohyd. Res. 1999, 322, 67-76.
20. Chen, M.; Diao, G.; Zhang, E. Chemosphere 2006, 63, 522-529.
21. Bailey, S. I.; Ritchie, I. M. Electrochim. Acta 1985, 30, 3-12
22. Ramos Cabrer, P.; Alvarez-Parrilla, E.; Meijide, F.; Seijas, J. A.; Rodríguez Núñez, E.; Vázquez Tato, J. Langmuir 1999, 15, 54895495.
23. Connors, K.A. Binding Constants: The Measurement of Molecular Complex Stability. John Wiley and Sons, Inc.: USA. 1987.
24. Jover, A.; Budal, R. M.; Meijide, F.; Soto, V. H.; Vázquez Tato, J. J. Phys. Chem. 2004, 108, 18850-18859.
25. Wiseman, T.; Williston, S.; Brandts, J. F.; Lin, L. N. Anal. Biochem. 1989, 179, 131-137.
26. Kono, Y.; Kashine, S.; Yoneyama, T.; Sakamoto, Y.; Matsui, Y.; Shibata, H. Biosci. Biotechnol. Biochem. 1998, 62, 22-27.
2. Hertog, M. G.; Kromhout, D.; Aravanis, C.; Blackburn, H.; Buzina, R.; Filanza, F.; Giampaoli, S.; Cansen, A.; Menotti, A.; Nedeljkovic, S. Arch. Intern. Med. 1995, 155, 381-386.
3. Jullian, C.; Orosteguis, T.; Pérez-Cruz, F.; Sánchez, P.; Mendizábal, F.; Olea-Azar, C. Spectrochim. Acta A. 2008, 71, 269-275.
4. Mourtzinos, I.; Makris, D. P.; Yannakopoulou, K.; Kalogeropoulos, N.; Machali, I.; Karathanos, V. T. J. Agric. Food Chem. 2008, 56, 10303-10310.
5. Lucas-Abellán, C.; Fortea, I.; Gabaldón, J. A.; Núñez-Delicado, E. J. Agric. Food Chem. 2008, 56, 255-259.
6. López-Nicolas, J. M.; Garcia-Carmona, F. J. Agric. Food Chem. 2007, 55, 6330-6338.
7. López-Nicolas, J. M.; Pérez-López, A.; Carbonell-Barrachina, A.; Garcia-Carmona, F. J. Agric. Food Chem. 2007, 55, 5312-5319.
8. Alvarez-Parrilla, E.; de la Rosa, L.A.; Rodrigo-Garcia, J.; Escobedo-Gonzalez, R.; Mercado-Mercado, G.; Moyers-Montoya, E.; Vazquez-Flores, A.; Gonzalez-Aguilar, G.A. Food Chem. 2007, 101, 1346-1356.
9. Queiroz, C.; Mendes Lopes, M. L.; Fialho, E.; Valente-Mequita, V. L. Food Rev. Int. 2008, 24, 361-375.
10. Gacche, R. N.; Zore, G. B.; Ghole, V. S. J. Enz. Inh. Med. Chem. 2003, 18, 1-5.
11. Casado-Vela, J.; Selles, S.; Bru, R. J. Food Biochem. 2006, 30, 623-640.
12. Fayad, N.; Marchal, L.; Billaud, C.; Nicolas, J. J. Agric. Food Chem. 1997, 45, 2442-2446.
13. Górnas, P.; Neunert, G.; Baczyñski, K.; Polewski, K. Food Chem. 2009, 114, 190-196.
14. Rodrigues, E.; Vaz, S.; Gil, V. M. S. S.; Caldeira, M. M.; Moreira de Silva, A. M. G. J. Inclusion Phenom. Macroxyclic Chem. 2002, 44, 395–397.
15. Shuang, S.-M.; Pan, J-H.; Guo, S.-Y.; Cai, M.-Y.; Liu, C.-S. Anal. Lett. 1997, 30, 2261-2270.
16. Alvarez-Parrilla, E.; Al-Soufi, W.; Ramos Cabrer, P.; Novo, M.; Vázquez Tato, J. J. Phys. Chem. B. 2001, 105, 5994-6003.
17. de Bôer, G.; Hanson, F. E. Entomol. Exp. Appl. 1987, 45, 123131.
18. Namazian, M.; Zare, H. R. Electrochim. Acta. 2005, 50, 43504355.
19. Irwin, P.; Brouillette, J.; Giampa, A.; Hicks, K.; Gering, A.; Tu, S.-I. Carbohyd. Res. 1999, 322, 67-76.
20. Chen, M.; Diao, G.; Zhang, E. Chemosphere 2006, 63, 522-529.
21. Bailey, S. I.; Ritchie, I. M. Electrochim. Acta 1985, 30, 3-12
22. Ramos Cabrer, P.; Alvarez-Parrilla, E.; Meijide, F.; Seijas, J. A.; Rodríguez Núñez, E.; Vázquez Tato, J. Langmuir 1999, 15, 54895495.
23. Connors, K.A. Binding Constants: The Measurement of Molecular Complex Stability. John Wiley and Sons, Inc.: USA. 1987.
24. Jover, A.; Budal, R. M.; Meijide, F.; Soto, V. H.; Vázquez Tato, J. J. Phys. Chem. 2004, 108, 18850-18859.
25. Wiseman, T.; Williston, S.; Brandts, J. F.; Lin, L. N. Anal. Biochem. 1989, 179, 131-137.
26. Kono, Y.; Kashine, S.; Yoneyama, T.; Sakamoto, Y.; Matsui, Y.; Shibata, H. Biosci. Biotechnol. Biochem. 1998, 62, 22-27.
Downloads
Published
2019-06-17
Issue
Section
Regular Articles
License
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
