Study of the molecular structure and chemical reactivity of pinocembrin by DFT calculations

Computational and Theoretical Chemistry

Volumn 1058, Issue , 2015, Pages 21-27

  Vargas Sanchez R D ^a   Mendoza Wilson, A M ^a   Balandran Quintana R R ^a   Torrescano Urrutia, G R ^a   Sanchez Escalante A ^a  

^a CENTRO DE INVESTIGACIÓN EN ALIMENTACIÓN Y DESARROLLO   (Mexico)

Author keywords

Chemical reactivity; DFT methods; Molecular structure; Pinocembrin

Indexed keywords

EID: 84923015823     PISSN: 2210271X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.comptc.2015.01.014     Document Type: Article

References (46)

1. Havsteen B.H. The biochemistry and medical significance of the flavonoids. Pharm. Therap. 2002, 96:67-202.
2. Seyoum A., Asres K., El-Fiky F.K. Structure-radical scavenging activity relationships of flavonoids. Phytochemistry 2006, 67:2058-2070.
3. Hernández J., Goycoolea F.M., Quintero J., Acosta A., Castañeda M., Domínguez Z., Robles R., Vázquez-Moreno L., Velázquez E.F., Astiazaran H., Lugo E., Velázquez C. Sonoran propolis: chemical composition and antiproliferative activity on cancer cell lines. Planta Med. 2007, 73:1469-1474.
4. Valencia D., Alday E., Robles-Zepeda R., Garibay-Escobar A., Gálvez-Ruiz J.C., Salas-Reyes M., Jiménez-Estrada M., Velázquez-Contreras E., Hernández J., Velázquez C. Seasonal effect on chemical composition and biological activities of Sonoran propolis. Food Chem. 2012, 131:645-651.
5. Neacsu M., Eklund P.C., Sjöholm R.E., Pietarinen S.P., Ahotupa M.O., Holmbom B.R. Antioxidant flavonoids from knotwood of Jack pine and European aspen. Holz Als Roh- und Werkstoff 2007, 65:1-6.
6. Zhao J., Li Y., Xue X.F., Cai Y. The study on the parts of higher activity of the flavones contents in propolis. Apicult. China 2005, 56:9-10.
7. Li-li S., Bain-nian C., Mei G., Heng-ai Z., Yan-jin L., Li W., Guan-hua D. The characteristics of therapeutic of pinocembrin in transient global brain ischemia/reperfusion rats. Life Sci. 2011, 88:521-528.
8. Liu R., Gao M., Zhi-Hong Y., Guan-Hua D. Pinocembrin protects rat brain against oxidation and apoptosis induced by ischemia-reperfusion both in vivo and in vitro. Brain Res. 2008, 1216:104-115.
9. D.U. Guanhua, L.V. Yang, W.U. Song, W. Ke, C. Ying, Y. Zhihong, B. Yuanfeng, G. Mei, Two Types of Crystalline of Pinocembrin: A And B, Their Preparation and Their Use for Manufacture of Pharmaceutical Compositions, European Patent Application, Patent 08878072.1, 2011.
10. Laskar R.A., Sk I., Roy N., Begum N.A. Antioxidant activity of Indian propolis and its chemical constituents. Food Chem. 2010, 122:233-237.
11. Payán-Gómez S.A., Flores-Holguín N., Pérez-Hernández A., Piñon-Miramontes M., Glossman-Mitnik D. Computational molecular characterization of the flavonoid rutin. Chem. Cent. J. 2010, 4:1-12.
12. Mendoza-Wilson A.M., Glossman-Mitnik D. Theoretical study of the molecular properties and chemical reactivity of (C)-catechin and (K)-epicatechin related to their antioxidant ability. J. Mol. Struct. THEOCHEM 2006, 761:97-106.
13. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E. Gaussian 03 Revision C.02 2004, Gaussian, Inc., Wallingford, CT.
14. Zhao Y., Truhlar D.G. A density functional that accounts for medium-range correlation energies in organic chemistry. Org. Lett. 2006, 8:5753-5755.
15. Yang Y., Gao H. Comparison of the performance of different DFT methods in the calculations of the molecular structure and vibration spectra of serotonin (5-hydroxytryptamine, 5-HT). J. Mol. Struct. 2012, 1013:111-118.
16. Cheeseman J.R., Trucks G.W., Keith T.A., Frisch J.M. A comparison of models for calculating nuclear magnetic resonance shielding tensors. Chem. Phys. 1996, 104:5497-5509.
17. Parr R.G., Yang W. Density Functional Theory of Atoms and Molecules 1989, Oxford University Press, New York.
18. Geerlings P., De Proft F., Langenaeker W. Conceptual density functional theory. Chem. Rev. 2003, 103:1793-1873.
19. Yang W., Mortier W.J. The use of global and local molecular parameters for the analysis of the gas-phase basicity of amines. J. Am. Chem. Soc. 1986, 108:5708-5711.
20. Marković Z.S., Marković J.M.D., Doličanin C.B. Mechanistic pathways for the reaction of quercetin with hydroperoxy radical. Theor. Chem. Acc. 2010, 127:69-80.
21. Harborne J.B., Mabry T.J. The Flavonoids: Advances in Research 1982, Hapman and Hall Ltd., London.
22. 1H-NMR simultaneous identification of health-relevant compounds in propolis extracts. Phytochem. Anal. 2011, 23:260-266.
23. Espinoza-Hicks J.C., Camacho-Dávila A.A., Flores-Holguín N.R., Nevárez-Moorillón G.V., Glossman-Mitnik D., Rodríguez-Valdez L.M. Experimental and quantum chemical studies of a novel synthetic prenylated chalcone. Chem. Cent. J. 2013, 7:17.
24. Sousa S.F., Fernandes P.A., Ramos M.J. General performance of density functionals. J. Phys. Chem. A 2007, 111:10439-10452.
25. Kudin K.N., Scuseria G.E., Martin R.L. Hybrid density-functional theory and the insulating gap of UO 2. Phys. Rev. Lett. 2002, 89:266402.
26. Lynch B.J., Truhlar D.G. How well can hybrid density functional methods predict transition state geometries and barrier heights?. J. Phys. Chem. A 2001, 105:2936-2941.
27. Zhao Y., Schultz N.E., Truhlar D.G. Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions. J. Chem. Theor. Comput. 2006, 2:364-382.
28. Foresman J.B., Frisch Æ. Exploring Chemistry with Electronic Structure Methods 1996, Gaussian, Pittsburgh, PA. second ed.
29. Raj G. Advanced Inorganic Chemistry, vol. 1 2008, Krishna Prakashan Media, India.
30. Parr R.G., Szentpály L.V., Liu S. Electrophilicity index. J. Am. Chem. Soc. 1999, 121:1922-1924.
31. Kondo K., Kurihara M., Miyata N., Suzuki T., Toyoda M. Mechanistic studies of catechins as antioxidants against radical oxidation. Arch. Biochem. Biophys. 1999, 362:79-86.
32. Pearson R.G. Chemical hardness and density functional theory. J. Chem. Sci. 2005, 177:369-377.
33. Glossman-Mitnik D. A comparison of the chemical reactivity of naringenin calculated with the M06 family of density functionals. Chem. Cent. J. 2013, 7:155.
34. Hassanzadeh K., Akhtari K., Hassanzadeh H., Zarei S.A., Fakhraei N., Hassanzadeh K. The role of structural CH compared with phenolic OH sites on the antioxidant activity of oleuropein and its derivatives as a great non-flavonoid family of the olive components: a DFT study. Food Chem. 2014, 164:251-258.
35. Pietta P.G. Flavonoids as antioxidants. J. Nat. Prod. 2000, 63:1035-1042.
36. Chen Z.Y., Chan P.T., Ho K.Y., Fung K.P., Wang J. Antioxidant activity of natural flavonoids is governed by number and location of their aromatic hydroxyl groups. Chem. Phys. Lipids 1996, 79:157-163.
37. Fedorowicz A., Mavri J., Bala P., Koll A. Molecular dynamics study of the tautomeric equilibrium in the Mannich base. Chem. Phys. Lett. 1998, 289:457-462.
38. J. Fals Guerra, Reactividad química de 1,3-bis-(2'-hidroxi-5'-clorobencil) imidazolidina (BISBIA) frente a fenoles y naftoles en condiciones libre de disolvente (Solvent-Free). Doctoral dissertation, Universidad Nacional de Colombia, 2012.
39. Trouillas P., Marsal P., Siri D., Lazzaroni R., Duroux J.L. A DFT study of the reactivity of OH groups in quercetin and taxifolin antioxidants: the specificity of the 3-OH site. Food Chem. 2006, 97:679-688.
40. Young D. Computational Chemistry: A Practical Guide for Applying Techniques to Real World Problems 2001, Wiley, New York.
41. Cruz J., Martínez-Aguilera L.M.R., Salcedo R., Castro M. Reactivity properties of derivatives of 2-imidazoline: an ab initio DFT study. Int. J. Quantum Chem. 2001, 85:546-556.
42. Mendoza-Wilson A.M., Glossman-Mitnik D. CHIH-DFT study of the electronic properties and chemical reactivity of quercetin. J. Mol. Struct. THEOCHEM 2005, 716:67-72.
43. Hyun J., Woo Y., Hwang D.S., Jo G., Eom S., Lee Y., Park J.C., Lim Y. Relationships between structures of hydroxyflavones and their antioxidative effects. Bioorg. Med. Chem. Lett. 2010, 20:5510-5513.
44. Viswas A., Tewari K. A Textbook of Organic Chemistry, 3E 2009, Vikas Publishing House Pvt Ltd.
45. Crabtree R.H. Energy Production and Storage: Inorganic Chemical Strategies for a Warming World 2010, John Wiley & Sons.
46. Denisov E.T., Denisova T.G., Pokidova T.S. Handbook of Free Radical Initiators 2005, John Wiley & Sons.