Theoretical study on the structural and antioxidant properties of some recently synthesised 2,4,5-trimethoxy chalcones

Food Chemistry

Volumn 171, Issue , 2015, Pages 89-97

  Wang, Guirong ^a   Xue, Yunsheng ^a   An, Lin ^a   Zheng, Youguang ^a   Dou, Yunyan ^a   Zhang, Ling ^a   Liu, Yi ^a  

^a XUZHOU MEDICAL UNIVERSITY   (China)

Author keywords

Chalcones; DFT; HAT; Radical scavenging activity; SET PT; SPLET

Indexed keywords

ANTIOXIDANTS; ATOMS; CHEMICAL BONDS; DISSOCIATION; ELECTRON AFFINITY; ELECTRON TRANSITIONS; ENTHALPY; FREE RADICAL REACTIONS; FREE RADICALS;

CHALCONES; DENSITY FUNCTIONAL THEORY METHODS; ELECTRON TRANSFER PROTON TRANSFERS; FREE RADICAL SCAVENGING ACTIVITY; HYDROGEN ATOM TRANSFERS (HAT); PHYSIOCHEMICAL PARAMETERS; RADICAL SCAVENGING ACTIVITY; SPLET;

DENSITY FUNCTIONAL THEORY;

2,4,5 TRIMETHOXY 2',5' DIHYDROXYCHALCONE; 2,4,5 TRIMETHOXY HYDROXYCHALCONE DERIVATIVE; ANTIOXIDANT; ASCORBIC ACID; BENZENE; CHALCONE DERIVATIVE; HYDROGEN; PHENOL; SOLVENT; UNCLASSIFIED DRUG; POLYPHENOL; SCAVENGER;

ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; DENSITY FUNCTIONAL THEORY; DRUG SYNTHESIS; ELECTRON TRANSPORT; ENTHALPY; HYDROGEN ATOM TRANSFER; HYDROGEN BOND; IONIZATION POTENTIAL; PHYSICAL CHEMISTRY; PROTON DISSOCIATION ENTHALPY; PROTON TRANSPORT; STEPWISE ELECTRON TRANSFER PROTON TRANSFER; THERMODYNAMICS; CHEMISTRY; OXIDATION REDUCTION REACTION;

ANTIOXIDANTS; CHALCONES; ELECTRON TRANSPORT; FREE RADICAL SCAVENGERS; OXIDATION-REDUCTION; POLYPHENOLS; SOLVENTS; THERMODYNAMICS;

EID: 84907210844     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2014.08.106     Document Type: Article

References (45)

1. M.E. Alberto, N. Russo, A. Grand, and A. Galano A physicochemical examination of the free radical scavenging activity of Trolox: Mechanism, kinetics and influence of the environment Physical Chemistry Chemical Physics 15 2013 4642 4650 10.1039/c3cp43319f
2. A. Amic, Z. Markovic, J.M. Dimitric Markovic, V. Stepanic, B. Lucic, and D. Amic Towards an improved prediction of the free radical scavenging potency of flavonoids: The significance of double PCET mechanisms Food Chemistry 152 2014 578 585 10.1016/j.foodchem.2013.12.025
3. E.H. Anouar, C.A. Calliste, P. Košinova, F. Di Meo, J.-L. Duroux, and Y. Champavier Free radical scavenging properties of guaiacol oligomers: A combined experimental and quantum study of the guaiacyl-moiety role Journal of Physical Chemistry A 113 50 2009 13881 13891 10.1021/jp906285b
4. J.E. Bartmess Thermodynamics of the electron and the proton Journal of Physical Chemistry 98 1994 6420 6424 10.1021/j100076a029
5. D.I. Batovska, and I.T. Todorova Trends in utilization of the pharmacological potential of chalcones Current Clinical Pharmacology 5 2010 1 29 10.2174/157488410790410579
6. A.D. Becke Density-functional thermochemistry III. The role of exact exchange Journal of Chemical Physics 98 1993 5648 5652 10.1063/1.464913
7. M.M. Bizarro, B.J. Costa Cabral, R.M.B. dos Santos, and J.A. Martinho Simões Substituent effects on the O-H bond dissociation enthalpies in phenolic compounds: Agreements and controversies Pure and Applied Chemistry 71 1999 1249 1256 10.1351/pac199971071249
8. C.A. Calliste, J.C. Le Bail, P. Trouillas, C. Pouget, G. Habrioux, and A.J. Chulia Chalcones: Structural requirements for antioxidant, estrogenic and antiproliferative activities Anticancer Research 21 2001 3949 3956
9. W.J. Chen, J.R. Song, P. Guo, and Z.Y. Wen Butein, a more effective antioxidant than α-tocopherol Journal of Molecular Structure: THEOCHEM 763 2006 161 164 10.1016/j.theochem.2005.12.035
10. J.J. Fifen, M. Nsangou, N. Dhaouadi, O. Motapon, and N. Jaidane Solvent effects on the antioxidant activity of 3,4-dihydroxyphenylpyruvic acid: DFT and TD-DFT studies Computational and Theoretical Chemistry 66 2011 232 243 10.1016/j.comptc.2011.03.006
11. M.C. Foti, C. Daquino, and C. Geraci Electron-transfer reaction of cinnamic acids and their methyl esters with the DPPH radical in alcoholic solutions Journal of Organic Chemistry 69 2004 2309 2314 10.1021/jo035758q
12. M. Francisco-Marquez, and A. Galano On the OH and OOH scavenging activity of 3-Methyl-1-pyridin-2-yl-5-pyrazolone: Comparisons with its parent compound, Edaravone International Journal of Quantum Chemistry 112 2012 3441 3448 10.1002/qua.24046
13. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, and J.R. Cheeseman Gaussian 09, Revision A.02 2009 Gaussian Inc Wallingford CT
14. M.L. Go, X. Wu, and X.L. Liu Chalcones: An update on cytotoxic and chemoprotective properties Current Medicinal Chemistry 12 2005 481 499 10.2174/0929867053363153
15. C. Iuga, J.R. Alvarez-Idaboy, and N. Russo Antioxidant activity of trans-resveratrol toward hydroxyl and hydroperoxyl radicals: A quantum chemical and computational kinetics study Journal of Organic Chemistry 77 2012 3868 3877 10.1021/jo3002134
16. D. Kozlowski, P. Trouillas, C. Calliste, P. Marsal, R. Lazzaroni, and J.L. Duroux Density functional theory study of the conformational, electronic, and antioxidant properties of natural chalcones Journal of Physical Chemistry A 111 2007 1138 1145 10.1021/jp066496
17. C. Lee, W. Yang, and R.G. Parr Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Physical Review B 37 1988 785 789 10.1103/PhysRevB.37.785
18. J. Lengyel, J. Rimarcik, A. Vaganekc, and E. Klein On the radical scavenging activity of isoflavones: Thermodynamics of O-H bond cleavage Physical Chemistry Chemical Physics 15 2013 10895 10903 10.1039/c3cp00095h
19. M. Leopoldini, S.G. Chiodo, N. Russo, and M. Toscano Detailed investigation of the OH radical quenching by natural antioxidant caffeic acid studied by quantum mechanical models Journal of Chemical Theory and Computation 7 2011 4218 4233 10.1021/ct200572p
20. M. Leopoldini, F. Rondinelli, N. Russo, and M. Toscano Pyranoanthocyanins: A theoretical investigation on their antioxidant activity Journal of Agricultural and Food Chemistry 58 2010 8862 8871 10.1021/jf101693k
21. M. Leopoldini, N. Russo, and M. Toscano Gas and liquid phase acidity of natural antioxidants Journal of Agricultural and Food Chemistry 54 2006 3078 3085 10.1021/jf053180a
22. M. Leopoldini, N. Russo, and M. Toscano The molecular basis of working mechanisms of natural polyphenolic antioxidants Food Chemistry 125 2011 288 306 10.1016/j.foodchem.2010.08.012
23. M.J. Li, W.X. Liu, C.R. Peng, Q.H. Ren, W.C. Lu, and W. Deng A DFT study on reaction of eupatilin with hydroxyl radical in solution International Journal of Quantum Chemistry 113 2013 966 974 10.1002/qua.24060
24. G. Litwinienko, and K.U. Ingold Solvent effects on the rates and mechanisms of reaction of phenols with free radicals Accounts of Chemical Research 40 3 2007 222 230 10.1021/ar0682029
25. A.C. Maritim, R.A. Sanders, and J.B. Watkins III Diabetes, oxidative stress, and antioxidants: A review Journal of Biochemical and Molecular Toxicology 17 2003 24 37 10.1002/jbt.10058
26. G. Mazzone, N. Malaj, N. Russo, and M. Toscano Density functional study of the antioxidant activity of some recently synthesized resveratrol analogues Food Chemistry 141 2013 2017 2024 10.1016/j.foodchem.2013.05.071
27. M. Musialik, and G. Litwinienko Abnormal solvent effects on hydrogen atom abstraction 2. Resolution of the curcumin antioxidant controversy. The role of sequential proton loss electron transfer Organic Letters 7 2005 4951 4954 10.1021/jo049254j
28. I. Nakanishi, T. Kawashima, K. Ohkubo, H. Kanazawa, K. Inami, and M. Mochizuki Electron-transfer mechanism in radical-scavenging reactions by a vitamin E model in a protic medium Organic Biomolecular Chemistry 3 2005 626 629 10.1039/B416572A
29. A.R. Ndhlala, M. Moyo, and J. Van Staden Natural antioxidants: Fascinating or mythical biomolecules? Molecules 15 2010 6905 6930 10.3390/molecules15106905
30. N. Nenadis, and M.P. Sigalas A DFT study on the radical scavenging potential of selected natural 3′,4′-dihydroxy aurones Food Research International 44 2011 114 120 10.1016/j.foodres.2010.10.054
31. N. Nenadis, and M.Z. Tsimidou Contribution of DFT computed molecular descriptors in the study of radical scavenging activity trend of natural hydroxybenzaldehydes and corresponding acids Food Research International 48 2012 538 543 10.1016/j.foodres.2012.05.014
32. V.D. Parker Homolytic bond (H-A) dissociation free energies in solution. Applications of the standard potential of the (H+/H.bul.) couple Journal of the American Chemical Society 114 1992 7458 7462 10.1021/ja00045a018
33. P.G. Pieta Flavonoids as antioxidants Journal of Natural Products 63 2000 1035 1042 10.1021/np9904509
34. B.M. Rezk, G.R. Haenen, W.J. van der Vijgh, and A. Bast The antioxidant activity of phloretin: The disclosure of a new antioxidant pharmacophore in flavonoids Biochemical and Biophysical Research Communications 295 2002 9 13 10.1016/S0006-291X(02)00618-6
35. J. Rimarcik, V. Lukes, E. Klein, and M. Ilcin Study of the solvent effect on the enthalpies of homolytic and heterolytic N-H bond cleavage in p-phenylenediamine and tetracyano- p-phenylenediamine Journal of Molecular Structure: THEOCHEM 925 2010 25 30 10.1016/j.theochem.2010.04.002
36. K. Sadasivama, and R. Kumaresan A comparative DFT study on the antioxidant activity of apigenin andscutellarein flavonoid compounds Molecular Physics 109 2011 839 852 10.1080/00268976.2011.556576
37. S. Shenvi, K. Kumar, K.S. Hatti, K. Rijesh, L. Diwakar, and G.C. Reddy Synthesis, anticancer and antioxidant activities of 2,4,5-trimethoxy chalcones and analogues from asaronaldehyde: Structure-activity relationship European Journal of Medicinal Chemistry 62 2013 435 442 10.1016/j.ejmech.2013.01.018
38. I.T. Todorova, D.I. Batovska, B.A. Stamboliyska, and S.P. Parushev Evaluation of the radical scavenging activity of a series of synthetic hydroxychalcones towards the DPPH radical Journal of the Serbian Chemical Society 76 2011 491 497 10.2298/JSC100517043T
39. J. Tomasi, B. Mennucci, and R. Cammi Quantum mechanical continuum solvation models Chemical Review 105 2005 2999 3094 10.1021/cr9904009
40. P. Trouillas, P. Marsal, D. Siri, R. Lazzaroni, and J.L. Duroux A DFT study of the reactivity of OH groups in quercetin and taxifolin antioxidants: The specificity of the 3-OH site Food Chemistry 97 2006 679 688 10.1016/j.foodchem.2005.05
41. J.S. Wright, E.R. Johnson, and G.A. DiLabio Predicting the activity of phenolic antioxidants: Theoretical method, analysis of substituent effects, and application to major families of antioxidants Journal of the American Chemical Society 123 2001 1173 1183 10.1021/ja002455u
42. Y.S. Xue, L. Zhang, Y.L. Li, D. Yu, Y.G. Zheng, and L. An A DFT study on the structure and radical scavenging activity of newly synthesized hydroxychalcones Journal of Physical Organic Chemistry 26 2013 240 248 10.1002/poc.3074
43. Y.S. Xue, Y.G. Zheng, L. An, Y.Y. Dou, and Y. Liu Density functional theory study of the structure-antioxidant activity of polyphenolic deoxybenzoins Food Chemistry 151 2014 198 206 10.1016/j.foodchem.2013.11.064
44. Y.S. Xue, Y.G. Zheng, L. An, Y. Qian, D. Yu, and X.D. Gong A theoretical study of the structure-radical scavenging activity of hydroxychalcones Computational and Theoretical Chemistry 982 2012 74 83 10.1016/j.comptc.2011.12.020
45. Y.S. Xue, Y.G. Zheng, L. Zhang, W.Y. Wu, D. Yu, and Y. Liu Theoretical study on the antioxidant properties of 2′-hydroxychalcones: H-atom vs. electron transfer mechanism Journal of Molecular Modeling 19 2013 3851 3862 10.1007/s00894-013-1921-x