Effect of pH on the complexation of kaempferol-4′-glucoside with three β-cyclodextrin derivatives: Isothermal titration calorimetry and spectroscopy study

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 1, 2014, Pages 244-250

  Zheng, Yan ^a   Dong, Li Na ^b   Liu, Min ^a   Chen, Aiju ^a   Feng, Shangcai ^c   Wang, Bingquan ^a   Sun, Dezhi ^a  

^a LIAOCHENG UNIVERSITY   (China)

^b Shandong Experimental High School   (China)

^c LINYI UNIVERSITY   (China)

Author keywords

cyclodextrin; complexation; isothermal titration calorimetry; kaempferol 4 glucoside; NMR; UV vis

Indexed keywords

CYCLODEXTRIN DERIVATIVES; ISOTHERMAL TITRATION CALORIMETRY; PHARMACEUTICAL INDUSTRY; PHOSPHATE BUFFER SOLUTIONS; PROTON NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STABILITY CONSTANTS; UV-VIS; UV-VIS ABSORPTIONS; KAEMPFEROL;

CALORIMETERS; CALORIMETRY; CARBOHYDRATES; COMPLEXATION; CYCLODEXTRINS; ENTHALPY; ISOTHERMS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TITRATION; MAGNETIC RESONANCE SPECTROSCOPY;

FLAVONOIDS;

BETA CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE; GLUCOSIDE; KAEMPFEROL; KAEMPFEROL DERIVATIVE;

CALORIMETRY; CHEMICAL STRUCTURE; CHEMISTRY; ENTROPY; PH; SOLUBILITY; SPECTROSCOPY;

BETA-CYCLODEXTRINS; CALORIMETRY; ENTROPY; GLUCOSIDES; HYDROGEN-ION CONCENTRATION; KAEMPFEROLS; MOLECULAR STRUCTURE; SOLUBILITY; SPECTRUM ANALYSIS;

EID: 84892175487     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf404320w     Document Type: Article

References (45)

1. Neuhouser, M. L. Dietary flavonoids and cancer risk: Evidence from human population studies Nutrit. Cancer 2004, 50, 1-7
2. Herrmann, K. Flavonols and flavones in food plants: a review J. Food Technol. 1976, 11, 433-448
3. Wojdyło, A.; Oszmianski, J.; Czemerys, R. Antioxidant activity and phenolic compounds in 32 selected herbs Food Chem. 2007, 105, 940-949
4. Park, Y. K.; Lee, C. Y. Identification of isorhamnetin 4′-glucoside in onions J. Agric. Food Chem. 1996, 44, 34-36
5. Jovanovic, S. V.; Steenken, S.; Tosic, M.; Marjanovic, B.; Simic, M. G. Flavonoids as antioxidants J. Am. Chem. Soc. 1994, 116, 4846-4851
6. Papadopoulou, A.; Green, R. J.; Frazier, R. A. Interaction of flavonoids with bovine serum albumin: A fluorescence quenching study J. Agric. Food Chem. 2005, 53, 158-163
7. Miean, K. H.; Mohamed, S. Flavonoid (myricetin, quercetin, kaempferol, luteolin, and apigenin) content of edible tropical plants J. Agric. Food Chem. 2001, 49, 3106-3112
8. Park, J. S.; Rho, H. S.; Kim, D. H.; Chang, I. S. Enzymatic preparation of kaempferol from green tea seed and its antioxidant activity J. Agric. Food Chem. 2006, 54, 2951-2956
9. Tu, Y. Ch.; Lian, T. W.; Yen, J. H.; Chen, Z. T.; Wu, M. J. Antiatherogenic effects of kaempferol and rhamnocitrin J. Agric. Food Chem. 2007, 55, 9969-9976
10. Chen, G. F.; Ma, X.; Meng, F. B.; Li, G. X. The electron transfer reactivity of kaempferol and its interaction with amino acid residues Bioelectrochemistry 2008, 72, 169-173
11. Chen, A. Y.; Chen, Y. Ch. A review of the dietary flavonoid, kaempferol on human health and cancer chemoprevention Food Chem. 2013, 138, 2099-2107
12. Iulia, M.; Sorana, I.; Mihaela, H. Kaempferol-human serum albumin interaction: characterization of the induced chirality upon binding by experimental circular dichroism and TDDFT calculations Spectrochim. Acta Part A 2012, 96, 709-715
13. Gee, J. M.; DuPont, M. S.; Rhodes, M. J. C.; Johnson, I. T. Quercetin glucosides interact with the intestinal glucose transport pathway Free Radic. Biol. Med. 1998, 25, 19-25
14. Zhu, X. Y.; Lin, H. M.; Chen, X.; Xie, J.; Wang, P. Mechanochemical- assisted extraction and antioxidant activities of kaempferol glycosides from Camellia oleifera Abel. meal J. Agric. Food Chem. 2011, 59, 3986-3993
15. Zhang, Q. F.; Nie, H. Ch.; Shangguang, X. Ch.; Yin, Zh. P.; Zheng, G. D.; Chen, J. G. Aqueous solubility and stability enhancement of astilbin through complexation with cyclodextrins J. Agric. Food Chem. 2013, 61, 151-156
16. Koontz, J. L.; Marcy, J. E. Formation of natamycin: cyclodextrin inclusion complexes and their characterization J. Agric. Food Chem. 2003, 51, 7106-7110
17. Liu, B. G.; Zhao, J.; Liu, Y. H.; Zhu, X. A.; Zeng, J. Physiochemical properties of the inclusion complex of puerarin and glucosyl-β-cyclodextrin J. Agric. Food Chem. 2012, 60, 12501-12507
18. Lucas-Abellán, C.; Fortea, I.; López-Nicolás, J. M.; Núnez-Delicado, E. Cyclodextrins as resveratrol carrier system Food Chem. 2007, 104, 39-44
19. Kurkov, S. V.; Loftsson, T. Cyclodextrins Int. J. Pharm. 2012, 453, 167-180
20. Mercader-Ros, M. T.; Lucas-Abellán, C.; Gabaldón, J. A.; Fortea, M. I.; Martínez-Cachá, A.; Núnez-Delicado, E. Kaempferol complexation in cyclodextrins at basic pH J. Agric. Food Chem. 2010, 58, 4675-4680
21. Bergonzi, M. C.; Bilia, A. R.; Bari, L. Di.; Mazzi, G.; Vincieri, F. Studies on interaction between some flavonols and cyclodextrins Bioorg. Med. Chem. Lett. 2007, 17, 5744-5748
22. Lucas-Abellán, C.; Fortea, I.; Gabaldón, J. A.; Núnez-Delicado, E. Encapsulation of quercetin and myricetin in cyclodextrins at acidic pH J. Agric. Food Chem. 2008, 56, 255-259
23. Mercader-Ros, M. T.; Lucas-Abellán, C.; Fortea, M. I.; Gabaldón, J. A.; Núnez-Delicado, E. Effect of HP-β- cyclodextrins complexation on the antioxidant activity of flavonols Food Chem. 2010, 118, 769-773
24. Jullian, C.; Brossard, V.; Gonzalez, I.; Alfaro, M.; Olea-Azar, C. Cyclodextrins-kaempferol inclusion complexes: Spectroscopic and reactivity studies J. Solution Chem. 2011, 40, 727-739
25. Kim, H.; Choi, J.; Jung, S. Inclusion complexes of modified cyclodextrins with some flavonols J. Incl. Phenom. Macrocycl. Chem. 2009, 64, 43-47
26. Bouchemal, K.; Mazzaferro, S. How to conduct and interpret ITC experiments accurately for cyclodextrin-guest interactions Drug Discovery Today. 2012, 17, 623-629
27. Liu, M.; Zhu, L.-Y.; Qu, X.-K.; Sun, D.-Zh.; Li, L.-W.; Lin, R.-S. Studies on the binding of paeonol and two of its isomers to human serum albumin by using microcalorimetry and circular dichroism J. Chem. Thermodyn. 2007, 39, 1565-1570
28. Veiga, F.; Teixeira-Dias, J. J. C.; Kedzierewicz, F.; Sousa, A.; Maincent, P. Inclusion complexation of tolbutamide with β-cyclodextrin and hydroxypropyl-β-cyclodextrin Int. J. Pharm. 1996, 129, 63-71
29. Jullian, C.; Moyano, L.; Yañez, C.; Olea-Azar, C. Complexation of quercetin with three kinds of cyclodextrins: An antioxidant study Spectrochim. Acta Part A 2007, 67, 230-234
30. Rekharsky, M. V.; Inoue, Y. Complexation and chiral recognition thermodynamics of 6-Amino-6-deoxy-β-cyclodextrin with anionic, cationic, and neutral chiral guests: Counterbalance between van der Waals and coulombic interactions J. Am. Chem. Soc. 2002, 124, 813-826
31. 7M-β-CD to HP-β-CD Pharm. Res. 2001, 18, 667-673
32. Zia, V.; Rajewski, R. A.; Stella, V. J. Thermodynamics of binding of neutral molecules to sulfobutyl ether β-cyclodextrins (SBE-β-CDs): The effect of total degree of substitution Pharm. Res. 2000, 17, 936-941
33. a shifts and binding affinities for cucurbit[7]uril and β-cyclodextrin J. Phys. Chem. B 2006, 110, 5132-5138
34. Terekhova, I. V. Comparative thermodynamic study on complex formation of native and hydroxypropylated cyclodextrins with benzoic acid Thermochim. Acta 2011, 526, 118-121
35. Smith, V. J.; Rougier, N. M.; Rossi, R. H.; Caira, M. R.; Buján, E. I.; Fernández, M. A.; Bourne, S. A. Investigation of the inclusion of the herbicide metobromuron in native cyclodextrins by powder X-ray diffraction and isothermal titration calorimetry Carbohydr. Res. 2009, 344, 2388-2393
36. Sandipan, C.; Soumalee, B.; Ansuman, L.; Soumen, B. Inclusion of chrysin in β-cyclodextrin nanocavity and its effect on antioxidant potential of chrysin: A spectroscopic and molecular modeling approach J. Mol. Struct. 2010, 977, 180-188
37. Lu, Zh.; Cheng, B.; Hu, Y. L.; Zhang, Y. H.; Zou, G. L. Complexation of resveratrol with cyclodextrins: Solubility and antioxidant activity Food Chem. 2009, 113, 17-20
38. Çelik, S. E.; Özyürek, M.; Tufan, A. N.; Güçlü, K.; Apak, R. Spectroscopic study and antioxidant properties of the inclusion complexes of rosmarinic acid with natural and derivative cyclodextrins Spectrochim. Acta Part A 2011, 78, 1615-1624
39. Wang, J.; Cao, Y. P.; Sun, B. G.; Wang, Ch. T. Characterisation of inclusion complex of trans-ferulic acid and hydroxypropyl-β-cyclodextrin Food Chem. 2011, 124, 1069-1075
40. Ibrahim, M. S.; Shehatta1, I. S.; Al-Nayeli, A. A. Voltammetric studies of the interaction of lumazine with cyclodextrins and DNA J. Pharm. Biomed. Anal. 2002, 28, 217-225
41. Fan, Y. X.; Li, J. F.; Dong, Ch. Preparation and study on the inclusion complexes of two tanshinone compounds with β-cyclodextrin Spectrochim. Acta Part A 2005, 61, 135-140
42. 1H NMR studies on host-guest interaction of paeonol and two of its isomers with β-cyclodextrin Int. J. Pharm. 2006, 316, 7-13
43. Yang, L. J.; Chen, W.; Ma, Sh. X.; Gao, Y. T.; Huang, R.; Yan, Sh. J.; Lin, J. Host-guest system of taxifolin and native cyclodextrin or its derivative: Preparation, characterization, inclusion mode, and solubilization Carbohyd. Polym. 2011, 85, 629-637
44. Zheng, Y.; Haworth, I. S.; Zuo, Z.; Chow, M. S. S.; Chow, A. H. L. Physicochemical and structural characterization of quercetin-β-cyclodextrin complexes J. Pharm. Sci. 2005, 94, 1079-1089
45. Yang, G. J.; Xu, J. J.; Chen, H. Y.; Leng, Z. Z. Studies on the interaction between rutin and DNA in the absence and presence of β-cyclodextrin by electrochemical and spectroscopic methods Chin. J. Chem. 2004, 22, 1325-1329