The role of electron-transfer and H-atom donation on the superb antioxidant activity and free radical reaction of curcumin

Food Chemistry

Volumn 135, Issue 3, 2012, Pages 1369-1376

  Barzegar, Abolfazl ^a,b  

^a UNIVERSITY OF TABRIZ   (Iran)

^b TABRIZ UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

Antioxidant; BDE; Curcumin; DFT; Electrochemistry; Electron transfer; Intracellular ROS

Indexed keywords

ANTIOXIDANT; BDE; CURCUMIN; DFT; ELECTRON-TRANSFER; INTRACELLULAR ROS;

CURING; ELECTROCHEMISTRY; ELECTRON TRANSITIONS; FREE RADICAL REACTIONS; ISOMERS; PHENOLS;

FREE RADICALS;

CURCUMIN; ENOLASE; FREE RADICAL; HYDROGEN; KETONE; REACTIVE OXYGEN METABOLITE; TROLOX C;

ANIMAL CELL; ANIMAL CELL CULTURE; ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CYCLIC POTENTIOMETRY; ELECTROCHEMISTRY; ELECTRON TRANSPORT; NONHUMAN; RAT; TAUTOMER;

ANTIOXIDANTS; CURCUMIN; ELECTRON TRANSPORT; FREE RADICALS; HYDROGEN-ION CONCENTRATION; MODELS, CHEMICAL; PHENOLS;

EID: 84862674171     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2012.05.070     Document Type: Article

References (28)

1. B.B. Aggarwal, C. Sundaram, N. Malani, and H. Ichikawa Curcumin: The Indian solid gold Advances in Experimental Medicine and Biology 595 2007 1 75
2. L.R.C. Barclay, M.R. Vinquist, K. Mukai, H. Goto, Y. Hashimoto, and A. Tokunaga On the antioxidant mechanism of curcumin: Classical methods are needed to determine antioxidant mechanism and activity Organic Letters 2 2000 2841 2843
3. A. Barzegar, M.D. Davari, N. Chaparzadeh, N. Zarghami, J.Z. Pedersen, and S. Incerpi Theoretical and experimental studies on the structure-antioxidant activity relationship of the synthetic 4-methylcoumarins Journal of Iranian Chemical Society 4 2011 973 981
4. A. Barzegar, J.Z. Pedersen, S. Incerpi, A.A. Moosavi-Movahedi, and L. Saso The mechanism of antioxidant activity of IRFI005 as a synthetic hydrophilic analogue of vitamin E Biochimie 93 2011 1880 1888
5. J. Berkowitz, G.B. Ellison, and D. Gutman Three Methods to Measure RH Bond Energies Journal of Physical Chemistry 98 1994 2744 2765
6. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, and J.R. Cheeseman Gaussian 98 1998 Gaussian Inc. Pittsburgh, PA
7. A. Gomes, E. Fernandes, and J.L.F.C. Lima Fluorescence probes used for detection of reactive oxygen species Journal of Biochemical and Biophysical Methods 65 2005 45 80 (Pubitemid 41827578)
8. A. Gomes, E. Fernandes, M.B. Garcia, A.M. Silva, D.C. Pinto, and C.M. Santos Cyclic voltammetric analysis of 2-styrylchromones: Relationship with the antioxi dant activity Bioorganic Medicinal Chemistry 16 2008 7939 7943
9. B. Halliwell, and M. Whiteman Measuring reactive species and oxidative damage in vivo and in cell culture: How should you do it and what do the results mean British Journal of Pharmacology 142 2004 231 255 (Pubitemid 38746160)
10. S.V. Jovanovic, S. Steenken, C.W. Boone, and G. Simic H-atom transfer is a preferred antioxidant mechanism of curcumin Journal of the American Chemical Society 121 1999 9677 9681
11. S.V. Jovanovic, C.W. Boone, S. Steenken, M. Trinoga, and R.B. Kaskey How curcumin works preferentially with water soluble antioxidants Journal of the American Chemical Society 123 2001 3064 3068 (Pubitemid 32879574)
12. S.M. Khopde, K.I. Priyadarsini, P. Venkatesan, and M.N.A. Rao Free radical scavenging ability and antioxidant efficiency of curcumin and its substituted analogue Biophysical Chemistry 80 1999 85 91
13. M. Lucarini, and G.F. Pedulli Bond dissociation enthalpy of α-tocopherol and other phenolic antioxidants Journal of Organic Chemistry 59 1994 5063 5070 (Pubitemid 24291852)
14. A. Lungu, I. Sandu, C. Boscornea, S. Tomas, and C. Mihailciuc Electrochemical study of curcumin and bisdemethoxycurcumin on activated glassy carbon electrode Revue Roumaine de Chimie 55 2010 109 115
15. S. Matsushita Antioxidant studies in retrospect O. Hayaishi, E. Niki, M. Kondo, T. Yoshikawa, Medical, biochemical and chemical aspects of free radicals Vol. 1 1988 Elsevier New York 327 334
16. K. Mukai, Y. Kageyama, T. Ishida, and K. Fukuda Synthesis and kinetic study of antioxidant activity of new tocopherol (vitamin E) compounds Journal Organic Chemistry 54 1989 552 556 (Pubitemid 19060205)
17. S. Nagaoka, A. Kuranaka, H. Tsuboi, U. Nagashima, and K. Mukai Mechanism of antioxidant reaction of vitamin E. Charge transfer and tunneling effect in proton-transfer reaction Journal of Physical Chemistry 96 1992 2754 2761
18. D. Njus, and P.M. Kelley Vitamins C and E donate single hydrogen atoms in vivo FEBS Letters 284 1991 147 151
19. A.C.P. Reddy, and B.R. Lokesh Studies on spice principles as antioxidants in the inhibition of lipid peroxidation of rat liver microsomes Molecular Cell Biochemistry 111 1992 117 124
20. R.A. Sharma, A.J. Gescher, and W.P. Steward Curcumin: The story so far European Journal of Cancer 41 2005 1955 1968 (Pubitemid 41557681)
21. M.Y. Song, J.Y. Yim, J.M. Yim, I.J. Kang, H.W. Rho, and H.S. Kim Use of curcumin to decrease nitric oxide production during the induction of antitumor responses by IL-2 Journal of Immunotherapy 34 2011 149 164
22. N. Sreejayan, and M.N.A. Rao Free radical scavenging activity of curcuminoids Arzneimittel Forschung - Drug Research 46 1996 169 171 (Pubitemid 26079147)
23. H.H. Tonnesen, and J.V. Greenhill Studies on curcumin and curcuminoids. XXII: Curcumin as a reducing agent and as a radical scavenger International Journal of Pharmaceutics 87 1992 79 87
24. S.S. Venkateswarlu, M.S. Ramachandra, and G.V. Subbaraju Synthesis and biological evaluation of polyhydroxycurcuminoids Bioorganic & Medicinal Chemistry 13 2005 6374 6380 (Pubitemid 41539301)
25. D.D.M. Wayner, E. Lusztyk, D. Page, K.U. Ingold, P. Mulder, and L.J.J.A. Laarhoven Effects of solvation on the enthalpies of reaction of tert-butoxyl radicals with phenol and on the calculated O-H bond strength in phenol Journal of the American Chemical Society 117 1995 8737 8744
26. R. Wilken, M.S. Veena, M.B. Wang, and E.S. Srivatsan Curcumin: A review of anti-cancer properties and therapeutic activity in head and neck squamous cell carcinoma Moecular Cancer 10 2011 1 19
27. J.S. Wright Predicting the antioxidant activity of curcumin and curcuminoids Journal of Molecular Structure (THEOCHEM) 591 2002 207 217
28. 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 (Pubitemid 32148182)