Influence of different free radicals on scavenging potency of gallic acid

Journal of Molecular Modeling

Volumn 20, Issue 7, 2014, Pages

  Dorović, Jelena ^a   Marković, Jasmina M Dimitrić ^b   Stepanić, Višnja ^c   Begović, Nebojša ^d   Amić, Dragan ^e   Marković, Zoran ^a,f  

^a Bioengineering Research and Development Center   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

^c RUDER BO KOVI INSTITUTE   (Croatia)

^d Institute of General and Physical Chemistry   (Serbia)

^e JOSIP JURAJ STROSSMAYER UNIVERSITY OF OSIJEK   (Croatia)

^f STATE UNIVERSITY OF NOVI PAZAR   (Serbia)

Author keywords

Bond dissociation enthalpy; DFT; Gallic acid; Proton affinity

Indexed keywords

ANION; ANTIOXIDANT; BENZENE; CAFFEIC ACID; CATION; DIMETHYL SULFOXIDE; EPICATECHIN; FREE RADICAL; GALLIC ACID; HYDROGEN; HYDROXYL GROUP; HYDROXYL RADICAL; PENTYLETHANOATE; PEROXY RADICAL; PHENOL DERIVATIVE; PROANTHOCYANIDIN; RESVERATROL; SCAVENGER; SOLVENT; SUPEROXIDE; UNCLASSIFIED DRUG; WATER; PROTON;

AQUEOUS SOLUTION; ARTICLE; BOND DISSOCIATION ENTHALPY; CONFORMATION; DENSITY FUNCTIONAL THEORY; DIELECTRIC CONSTANT; ELECTRON; ELECTRON TRANSPORT; ENERGY TRANSFER; ENTHALPY; HYDROGEN ATOM TRANSFER; HYDROGEN BOND; IONIZATION POTENTIAL; PRIORITY JOURNAL; PROTON AFFINITY; PROTON TRANSPORT; REACTION ANALYSIS; SEQUENTIAL PROTON LOSS ELECTRON TRANSFER; SINGLE ELECTRON TRANSFER FOLLOWED BY PROTON TRANSFER; SOLVATION; THERMODYNAMICS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; COMPUTER SIMULATION; STRUCTURE ACTIVITY RELATION;

COMPUTER SIMULATION; ELECTRONS; FREE RADICAL SCAVENGERS; FREE RADICALS; GALLIC ACID; HYDROGEN; HYDROGEN BONDING; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PROTONS; SOLVENTS; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS;

EID: 84904819931     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-014-2345-y     Document Type: Article

References (41)

1. Bianco M-A, Handaji A, Savolainen H (1998) Quantitative analysis of ellagic acid in hardwood samples. Sci Total Environ 222:123-126 (Pubitemid 28479820)
2. Pettersen RC, Ward JC, Lawrence AH (1993) Detection of northern red oak wetwood by fast heating and ion mobility spectrometric analysis. Holzforschung 47:513-522
3. Koga T, Moro K, Nakamori K, Yamakoshi J, Hosoyama H, Kataoka S, Ariga T (1999) Increase of antioxidative potential of rat plasma by oral administration of proanthocyanidin-rich extract from grape seeds. J Agric Food Chem 47:1892-1897 (Pubitemid 29438732)
4. Burns J, Gardner PT, O'Neil J, Crawford S, Morecroft I, McPhail DB, Lister C, Matthews D, MacLean MR, Lean MEJ, Duthie GG, Crozier A (2000) Relantionship among antioxidant activity, vasodilation capacity, and phenolic content of red wines. J Agric Food Chem 48:220-230 (Pubitemid 30120345)
5. Sakagami H, Yokote Y, Akahane K (2001) Changes in amino acid pool and utilization during apoptosis in HL-60 cells induced by epigallocatechin gallate or gallic acid. Anticancer Res 21:2441-2447 (Pubitemid 33054408)
6. Krilov A, Holmgren A, Gref R, Öhman L-O (1993) Effect of gallic acid on metals: an FT-IR study of complexes between gallic acid and sawblade steel. Holzforschung 47:239-246
7. Shukla YN, Srivastava A, Kumar S, Kumar S (1999) Phytotoxic and antimicrobial constituents of Argyreia speciosa and Oenothera biennis. J Ethnopharmacol 67:241-245 (Pubitemid 29421682)
8. Gutteridge JMC, Halliwell B (1994) Antioxidants in nutrition, health, and disease, 1st edn. Oxford University Press, Oxford
9. Rice-Evans CA, Miller NJ, Paganga G (1996) Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Med 20:933-956 (Pubitemid 26157509)
10. Klein E, Lukeš V, Ilčin M (2007) DFT/B3LYP study of tocopherols and chromans antioxidant action energetics. Chem Phys 336:51-57
11. Litwinienko G, Ingold KU (2007) Solvent effects on the rates and mechanisms of reaction of phenols with free radicals. Acc Chem Res 40:222-230
12. Di Meo F, Lemaur V, Cornil J, Lazzaroni R, Duroux J-L, Olivier Y, Trouillas P (2013) Free radical scavenging by natural polyphenols: atom versus electron transfer. J Phys Chem A 117:2082-2092
13. • radical in alcoholic solutions. J Org Chem 69:2309-2314
14. Marković Z, Milenković D, Crossed D signorović J, Jeremić S (2013) Solvation enthalpies of the proton and electron in polar and non-polar solvents. J Serb Soc Comput Mech 7:1-9
15. Bartmess JE (1994) Thermodynamics of the electron and the proton. J Phys Chem 98:6420-6424
16. Zhao Y, Schultz NE, Truhlar DG (2005) Exchange-correlation functional with broad accuracy for metallic and nonmetallic compounds, kinetics, and noncovalent interactions. J Chem Phys 123(1 - 4):161103
17. McLean AD, Chandler GS (1980) Contracted gaussian basis sets for molecular calculations. I. Second row atoms, Z=11-18. J Chem Phys 72:5639-5648
18. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick AD, Rabuck KD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, HeadGordon M, Replogle ES, Pople JA (2010) Gaussian 09, revision C.01. Gaussian Inc, Wallingford
19. 2 from n-butanol-a simple yet exacting test for model chemistries? J Comput Chem 31:1236-1248
20. Galano A, Macias-Ruvalcaba NA, Medina-Campos ON, Pedraza-Chaverri J (2010) Mechanism of the OH radical scavenging activity of nordihydroguaiaretic acid: a combined theoretical and experimental study. J Phys Chem B 114:6625-6635
21. Marković ZS, Dimitrić Marković JM, Doličanin ĆB (2010) Mechanistic pathways for the reaction of quercetin with hydroperoxy radical. Theor Chem Accounts 127:69-80
22. Zavala-Oseguera C, Alvarez-Idaboy JR, Merino G, Galano A (2009) OH radical gas phase reactions with aliphatic ethers: a variational transition state theory study. J Phys Chem A 113:13913-13920
23. Alberto ME, Russo N, Grand A, Galano A (2013) A physicochemical examination of the free radical scavenging activity of Trolox: mechanism, kinetics and influence of the environment. Phys Chem Chem Phys 15:4642-4650
24. Marković Z, Milenković D, Crossed D signorović J, Dimitrić Marković JM, Stepanić V, Lučić B, Amić D (2012) PM6 and DFT study of free radical scavenging activity of morin. Food Chem 134:1754-1760
25. Grimme S (2011) Density functional theory with London dispersion corrections. WIREs Comput Mol Sci 1:211-228
26. Grimme S (2006) Semiempirical GGA-type density functional constructed with a long-range dispersion coorrection. J Comput Chem 27:1787-1799
27. Bayach I, Sancho-García JC, Di Meo F, Weber J-FF, Trouillas P (2013) π-stacked polyphenolic dimers: a case study using dispersion-corrected methods. Chem Phys Lett 578:120-125
28. Becke AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648-5652
29. Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785-789
30. Carpenter JE, Weinhold F (1988) Analysis of the geometry of the hydroxymethyl radical by the "different hybrids for different spins" natural bond orbital procedure. J Mol Struct (Theochem) 169:41-62
31. Reed AE, Curtiss LA, Weinhold F (1988) Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem Rev 88:899-926
32. Medina ME, Iuga C, Alvarez-Idaboy JR (2013) Antioxidant activity of propyl gallate in aqueous and lipid media: a theoretical study. Phys Chem Chem Phys 15:13137-13146
33. Marenich AV, Cramer CJ, Truhlar DG (2009) Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. J Phys Chem B 113:6378-6396
34. - radicals. J Mol Struct (Theochem) 850:135-143
35. Leopoldini M, Marino T, Russo N, Toscano M (2004) Antioxidant properties of phenolic compounds: H-atom versus electron transfer mechanism. J Phys Chem A 108:4916-4922
36. Marković ZS, Dimitrić-Marković JM, Milenković D, Filipović N (2011) Structural and electronic features of baicalein and its radicals. Monatsh Chem 142:145-152
37. Rimarčik J, Lukeš V, Klein E, Ilčin M (2010) Study of the solvent effect on the enthalpies of homolytic and heterolytic N - H bond cleavage in p-phenylenediamine and tetracyano-p-phenylenediamine. J Mol Struct (Theochem) 952:25-30
38. Vaganek A, Rimarčik J, Lukeš V, Klein E (2012) On the energetics of homolytic and heterolytic O - H bond cleavage in flavonoids. Comp Theor Chem 991:192-200
39. Shahidi F, Janitha PK, Wanasundara PD (1992) Phenolic antioxidants. Crit Rev Food Sci Nutr 32:67-103
40. Hussein MA (2011) A convenient mechanism for the free radical scavenging activity of resveratrol. Int J Phytomed 3:459-469
41. Fang Y-Z, Yang S, Wu G (2002) Free radicals, antioxidants, and nutrition. Nutrition 18:872-879 (Pubitemid 35292261)