Physicochemical investigation and molecular modeling of cyclodextrin complexation mechanism with eugenol

Food Research International

Volumn 42, Issue 8, 2009, Pages 1178-1185

  Nuchuchua, Onanong ^a   Saesoo, Somsak ^a   Sramala, Issara ^a   Puttipipatkhachorn, Satit ^b   Soottitantawat, Apinan ^c   Ruktanonchai, Uracha ^a  

^a NATIONAL SCIENCE AND TECHNOLOGY DEVELOPMENT AGENCY   (Thailand)

^b MAHIDOL UNIVERSITY   (Thailand)

^c CHULALONGKORN UNIVERSITY   (Thailand)

Author keywords

Cyclodextrin; Eugenol; Inclusion complexes; Molecular modeling

Indexed keywords

AQUEOUS PHASE; CAVITY SIZE; CDS; COMPLEX FORMATIONS; COMPLEXATION MECHANISMS; ENERGY OF SOLVATION; EUGENOL; EXPERIMENTAL OBSERVATION; HYDROPHILIC SURFACES; HYDROPHOBIC CAVITIES; IN-SILICO; INCLUSION COMPLEX; INCLUSION COMPLEXES; INTERMOLECULAR FORCES; INTERMOLECULAR HYDROGEN BONDING; MOLE RATIO; RELEASE PROFILES; STABLE COMPLEXES; THERMAL ANALYSIS; THERMODYNAMIC DATA;

AROMATIC COMPOUNDS; CYCLODEXTRINS; HYDROGEN; HYDROGEN BONDS; HYDROPHOBICITY; MOLECULAR MODELING; SILANES; THERMOANALYSIS;

DATA STORAGE EQUIPMENT;

INSECTIVORA;

EID: 67650951106     PISSN: 09639969     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodres.2009.06.006     Document Type: Article

References (29)

1. Atsumi T., Iwakura I., Fujisawa S., and Ueha T. Reactive oxygen species generation and photo-cytotoxicity of eugenol in solutions of various pH. Biomaterials 22 (2001) 1459-1466
2. Choi M.J., Soottitantawat A., Nuchuchua O., Min S.G., and Ruktanonchai U. Physical and light oxidative properties of eugenol encapsulated by molecular inclusion and emulsion-diffusion method. Food Research International 42 (2009) 149-156
3. Desiraju G.R. The C-H⋯O hydrogen bond: Structural implications and supramolecular design. Account of Chemical Research 29 44 (1996) 1-449
4. Divakar S., and Maheswaran M.M. Structural studies on inclusion compounds of β-cyclodextrin with some substituted phenols. Journal of Inclusion Phenomena and Macrocyclic Chemistry 27 (1997) 113-126
5. Drakulić B.J., Juranić I.O., Erić S., and Zloh M. Role of complexes formation between drugs and penetration enhancers in transdermal delivery. International Journal of Pharmaceutics 363 1-2 (2008) 40-49
6. Fermeglia M., Ferrone M., Lodi A., and Pricl S. Host-guest inclusion complexes between anticancer drugs and β-cyclodextrin: Computational studies. Carbohydrate Polymer 53 (2003) 15-44
7. Filippa M., Sancho M.I., and Gasull E. Encapsulation of methyl and ethyl salicylates by β-cyclodextrin HPLC, UV-vis and molecular modeling studies. Journal of Pharmaceutical and Biomedical Analysis 48 (2008) 969-973
8. Francoa C., Schwingel L., Lulab I., Sinisterrab R.D., Koester L.S., and Bassani V.L. Studies on coumestrol/β-cyclodextrin association: Inclusion complex characterization. International Journal of Pharmaceutics 369 (2009) 5-11
9. Fujisawa S., Atsumi T., Kadoma Y., and Sakagami H. Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity. Toxicology 177 (2002) 39-54
10. Georg H.C., Coutinho K., and Canuto S. A look inside the cavity of hydrated α-cyclodextrin: A computer simulation study. Chemical Physics Letters 413 (2005) 16-21
11. Górnas P., Neunert G., Baczyński K., and Polewski K. Beta-cyclodextrin complexes with chlorogenic and caffeic acids from coffee brew: Spectroscopic thermodynamic and molecular modeling study. Food Chemistry 114 1 (2009) 190-196
12. Huang M.J., Watts J.D., and Bodor N. Theoretical studies of inclusion complexes of β-cyclodextrin with methylated benzoic acids. International Journal of Quantum Chemistry 64 (1997) 711-719
13. Ito M., Murakami K., and Yoshino M. Antioxidant action of eugenol compounds: Role of metal ion in the inhibition of lipid peroxidation. Food Chemistry Toxicololgy 43 (2005) 461-466
14. Kalemba D., and Kunicka A. Antibacterial and antifungal properties of essential oils. Current Medicinal Chemistry 10 (2003) 813-829
15. Laekeman S.M., Hoof V.L., Haemers A., Berghe V.A.D., Herman A.G., and Vlietink A.K. Eugenol A valuable compound for in vitro experimental research and worthwhile for further in vivo investigation. Phytotherapy Research 4 3 (1990) 90-96
16. Liu X.D., Furata T., Yoshii H., Linko P., and Jan Coumans W. Cyclodextrin encapsulation to prevent the loss of l-menthol and its retention during drying. Bioscience, Biotechnology and Biochemistry 64 8 (2000) 1608-1613
17. Liu L., and Zhu S. A study on the supramolecular structure of inclusion complex of β-cyclodextrin with prazosin hydrochloride. Carbohydrate Polymers 68 3 (2007) 472-476
18. Ohakubo T., and Shibata M. The selective capsaicin receptor antagonist capsazepine abolishes the antinociceptive actions of eugenol and guaiacol. Journal of Dental Research 76 4 (1997) 848-851
19. Ou H.C., Chou F.P., Lin T.M., Yang C.H., and Sheu W.H. Protective effects of eugenol against oxidized LDL-induced cytotoxicity and adhesion molecule expression in endothelial cells. Food Chemistry Toxicololgy 44 (2006) 1485-1495
20. Son K.H., Kwon S.Y., Kim H.P., Chang H.W., and Kang S.S. Constituents of syzigium aromaticum Merr. et Perry. Natural Product Sciences 4 4 (1998) 263-267
21. Steiner Th. Unrolling the hydrogen bond properties of C-H⋯O interactions. Chemistry Communication 727 (1997) 734
22. Szejtli J. Past, present, and future of cyclodextrin Research. Pure and Applied Chemistry 76 10 (2004) 1825-1845
23. Szente L., and Szejtli J. Highly soluble cyclodextrin derivatives: Chemistry, properties, and trends in development. Advanced Drug Delivery Reviews 36 (1999) 17-28
24. Szente L., and Szejtli J. Cyclodextrins as food ingredients. Trends in Food Science and Technology 15 (2004) 137-142
25. Veiga F., Teixeira-Dias J.J.C., Kedzierewicz F., Sousa A., and Maincent P. Inclusion complexation of tolbutamide with β-cyclodextrin and hydroxypropyl β-cyclodextrin. International Journal of Pharmacuetics 129 (1996) 63-71
26. Wang J.H., and Cai Z. Investigation of inclusion complex of miconazole nitrate with β-cyclodextrin. Carbohydrate Polymers 72 2 (2008) 255-260
27. Yan C., Xiu Z., Li X., and Hao C. Molecular modeling study of β-cyclodextrin complexes with (+)-catechin and (-)-epicatechin. Journal of Molecular Graphics and Modeling 26 (2007) 420-428
28. Yang Y., and Song L.X. Study on the inclusion compounds of eugenol with α-, β-, γ- and Heptakis (2, 6-di-O-methyl) β-cyclodextrins. Journal of Inclusion Phenomena and Macrocyclic Chemistry 53 (2005) 27-33
29. Zhan H., Jiang Z., Wang Y., Li R., and Dong T. Molecular microcapsules and inclusion interactions of eugenol with β-cyclodextrin and its derivatives. European Food Research and Technology 227 5 (2008) 1507-1513