Antioxidant mechanisms of quercetin and myricetin in the gas phase and in solution- A comparison and validation of semi-empirical methods

Journal of Molecular Modeling

Volumn 16, Issue 5, 2010, Pages 863-876

  Justino, Gonçalo C ^a   Vieira, Abel J S C ^a  

^a UNIVERSIDADE NOVA DE LISBOA   (Portugal)

Author keywords

Antioxidant mechanism; Flavonoids; Semi empirical methods

Indexed keywords

ALPHA TOCOPHEROL; HYDROGEN; MYRICETIN; QUERCETIN; ANTIOXIDANT; FLAVONOID; FLAVONOL DERIVATIVE;

ANTIOXIDANT ACTIVITY; ARTICLE; CALCULATION; CHEMICAL STRUCTURE; COMPARATIVE STUDY; DENSITY FUNCTIONAL THEORY; ELECTRON TRANSPORT; GAS; GEOMETRY; IONIZATION; MOLECULAR DYNAMICS; MOLECULAR STABILITY; MOLECULE; PRIORITY JOURNAL; PROTON TRANSPORT; SOLUTION AND SOLUBILITY; STRUCTURE ACTIVITY RELATION; CHEMISTRY;

ANTIOXIDANTS; FLAVONOIDS; FLAVONOLS; GASES; PHARMACEUTICAL SOLUTIONS; QUERCETIN; SOLUTIONS;

EID: 77953940511     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-009-0583-1     Document Type: Article

References (62)

1. Manach C, Scalbert A, Morand C, Rémésy C, Jiménez L (2004) Polyphenols: food sources and bioavailability. Am J Clin Nutr 79:727-747.
2. Birt DF, Hendrich S, Wang W (2001) Dietary agents in cancer prevention: flavonoids and isoflavonoids. Pharmacol Ther 90:157-177. doi:10.1016/S0163- 7258(01)00137-1. (Pubitemid 32913477)
3. Bors W, Michel C (2002) Chemistry of the antioxidant effect of polyphenols. Ann N Y Acad Sci 957:57-69. doi:10.1111/j.1749-6632.2002.tb02905.x.
4. Halliwell B, Rafter J, Jenner A (2005) Health promotion by flavonoids, tocopherols, tocotrienols, and other phenols: direct or indirect effects? Antioxidant or not? Am J Clin Nutr 81(1 Suppl): 268S-276S.
5. Williamson G, Manach C (2005) Bioavailability and bioefficacy of polyphenols in humans. II. Review of 93 intervention studies. Am J Clin Nutr 81(1 Suppl):243S-255S.
6. Gomes A, Fernandes E, Lima JL, Mira L, Corvo ML (2008) Molecular mechanisms of anti-inflammatory activity mediated by flavonoids. Curr Med Chem 15:1586-1605.
7. Friedman M (2007) Overview of antibacterial, antitoxin, antiviral, and antifungal activities of tea flavonoids and teas. Mol Nutr Food Res 51:116-134. doi:10.1002/mnfr.200600173. (Pubitemid 46144767)
8. Biesalski HK (2007) 9: Polyphenols and inflammation: basic interactions. Curr Opin Clin Nutr Metab Care 10:724-728.
9. Wang Y, Yang L, He YQ, Wang CH, Welbeck EW, Bligh SWA, Wang ZT (2008) Characterization of fifty-one flavonoids in a Chinese herbal prescription Longdan Xiegan Decoction by highperformance liquid chromatography coupled to electrospray ionization tandem mass spectrometry and photodiode array detection. Rapid Commun Mass Spectrom 22:1767-1778. doi:10.1002/rcm.3536. (Pubitemid 351947741)
10. Heinrich M (2003) Ethnobotany and natural products: the search for new molecules, new treatments of old diseases or a better understanding of indigenous cultures? Curr Top Med Chem 3:29-42.
11. Arts IC (2008) A review of the epidemiological evidence on tea, flavonoids, and lung cancer. J Nutr 138:1561S-1566S.
12. Tomar RS, Shiao R (2008) Early life and adult exposure to isoflavones and breast cancer risk. J Environ Sci Health C Environ Carcinog Ecotoxicol Rev 26:113-173. doi:10.1080/10590500802074256. (Pubitemid 352000641)
13. Linseisen J, Rohrmann S (2008) Biomarkers of dietary intake of flavonoids and phenolic acids for studying diet-cancer relationship in humans. Eur J Nutr 47:60-68. doi:10.1007/s00394-008-2007-x. (Pubitemid 351644181)
14. de Kok TM, van Breda SG, Manson MM (2008) Mechanisms of combined action of different chemopreventive dietary compounds: a review. Eur J Nutr 47(Suppl 2):51-59. doi:10.1007/s00394-008-2006-y. (Pubitemid 351644180)
15. Manach C, Williamson G, Morand C, Scalbert A, Remesy C (2005) Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. Am J Clin Nutr 81(1 Suppl): 230S-242S.
16. Boots AW, Haenen GR, Bast A (2008) Health effects of quercetin: from antioxidant to nutraceutical. Eur J Pharmacol 585:325-327. doi:10.1016/j.ejphar. 2008.03.008.
17. Oyama Y, Fuchs PA, Katayama N, Noda K (1994) Myricetin and quercetin, the flavonoid constituents of Ginkgo biloba extract, greatly reduce oxidative metabolism in both resting and Ca(2+)-loaded brain neurons. Brain Res 635:125-129. doi:10.1016/0006-8993(94)91431-1.
18. Gordon MH, Roedig-Penmanm A (1998) Antioxidant activity of quercetin and myricetin in liposomes. Chem Phys Lipids 97:79-85. doi:10.1016/S0009-3084(98) 00098-X. (Pubitemid 28557016)
19. Furuno K, Akasako T, Sugihara N (2002) The contribution of the pyrogallol moiety to the superoxide radical scavenging activity of flavonoids. Biol Pharm Bull 25:19-23. doi:10.1248/bpb.25.19.
20. Zhang H-Y, Sun Y-M, Wang X-L (2003) Substituent effects on O-H bond dissociation enthalpies and ionization potentials of catechols: A DFT study and its implications in the rational design of phenolic antioxidants and elucidation of structure-activity relationships for flavonoid antioxidants. Chem Eur J 9:502-508. doi:10.1002/chem.200390052.
21. 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. doi:10.1021/ar0682029.
22. Mayo SL, Olafson BD, Goddard WA III (1990) DREIDING: a generic force field for molecular simulations. J Phys Chem 94:8897-8909. doi:10.1021/ j100389a010.
23. Marvin version 5.00 and Calculator Plugins for Marvin 500 2008 ChemAxon (http://wwwchemaxoncom).
24. MOPAC2009 James J P Stewart Stewart Computational Chemistry Version 9034 L. http://OpenMOPACnet.
25. Baker J (1986) An algorithm for the location of transition states. J Comp Chem 7:385-395. doi:10.1002/jcc.540070402.
26. Dewar MJS, Thiel W (1977) Ground states of molecules. 38. The MNDO method. Approximations and parameters. J Am Chem Soc 99:4899-4907. doi:10.1021/ja00457a004.
27. Dewar MJS, Zoebisch EG, Healy EF, Stewart JJP (1985) Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model. J Am Chem Soc 107:3902-3909. doi:10.1021/ja0029 9a024.
28. Rocha GB, Freire RO, Simas AM, Stewart JJP (2006) RM1: A reparameterization of AM1 for H, C, N, O, P, S, F, Cl, Br, and I. J Comp Chem 27:1101-1111. doi:10.1002/jcc.20425. (Pubitemid 43989803)
29. Stewart JJP (1989) Optimization of parameters for semiempirical methods I. Method J Comp Chem 10:209-220. doi:10.1002/jcc.540100208.
30. Stewart JJP (2007) Optimization of parameters for semiempirical methods V: modification of NDDO approximations and application to 70 elements. J Mol Modeling 13:1173-1213. doi:10.1007/s00894-007-0233-4. (Pubitemid 47629446)
31. Klamt A, Schüürmann G (1993) COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient. J Chem Soc Perkin Trans 2:799-805. doi:10.1039/ P29930000799.
32. Antonczak S (2008) Electronic description of four flavonoids revisited by DFT method. THEOCHEM 856:38-45. doi:10.1016/j.theochem.2008.01.014.
33. Fiorucci S, Golebiowski J, Cabrol-Bass D, Antonczak S (2007) DFT study of quercetin activated forms involved in antiradical, antioxidant, and prooxidant biological processes. J Agric Food Chem 55:903-911. doi:10.1021/jf061864s.
34. Klein E, Lukeš V, Ilčin M (2007) DFT/B3LYP study of tocopherols and chromans antioxidant action energetics. Chem Phys 336:51-57. doi:10.1016/j.chemphys.2007.05.007.
35. Lide DA (2004) CRC handbook chemistry and physics. CRC Press Inc, Boca Raton, FL, USA.
36. Parr RG, Szentpály L, Liu S (1999) Electrophilicity index. J Am Chem Soc 121:1922-1924. doi:10.1021/ja983494x. (Pubitemid 29132049)
37. Mendoza-Wilson AM, Glossman-Mitnik D (2005) CHIH-DFT study of the electronic properties and chemical reactivity of quercetin. THEOCHEM 716:67-72. doi:10.1016/j.theochem.2004.10.083. (Pubitemid 40320768)
38. Vasilescu D, Girma R (2002) Quantum molecular modeling of quercetin - simulation of the interaction with the free radical t-BuOO. Int J Quantum Chem 90:888-902. doi:10.1002/qua.1801.
39. Russo N, Toscano M, Occella N (2000) Semiempirical molecular modeling into quercetin reactive site: structural, conformational, and electronic features. J Agric Food Chem 48:3232-3237. doi:10.1021/jf990469h.
40. 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. doi:10.1021/jp037247d.
41. Leopoldini M, Russo N, Toscano M (2006) Gas and liquid phase acidity of natural antioxidants. J Agric Food Chem 54:3078-3085. doi:10.1021/jf053180a.
42. Leopoldini M, Marino T, Russo N, Toscano M (2004) Density functional computations of the energetic and spectroscopic parameters of quercetin and its radicals in the gas phase and in solvent. Theor Chem Acc 111:210-216. doi:10.1007/s00214-003-0544-1.
43. Carpenter JE, Weinhold F (1988) Analysis of the geometry of the hydroxymethyl radical by the "different hybrids for different spins" natural bond orbital procedure. THEOCHEM 169:41-62. doi:10.1016/0166-1280(88) 80248-3.
44. Carpenter JE, Reed WF, AE WF (1985) Natural localized molecular orbitals. J Chem Phys 83:1736-1740. doi:10.1063/1.449360.
45. Cornard JP, Merlin JC, Boudet AC, Vrielynck L (1997) Structural study of quercetin by vibrational and electronic spectroscopies combined with semiempirical calculations. Biospectroscopy 3:183-193. doi:10.1002/(SICI)1520- 6343(1997)3:3<183::AID-BS PY2>3.0.CO;2-7. (Pubitemid 127778606)
46. van Acker SABE, de Groot MJ, van den Berg M-J, Tromp MNJL, den Kelder GD-O, Vijgh WJF, Bast A (1996) A quantum chemical explanation of the antioxidant activity of flavonoids. Chem Res Toxicol 9:1305-1312. doi:10.1021/tx9600964. (Pubitemid 26403836)
47. Yates PC (1991) Semi-empirical molecular orbital calculations on tyrosine kinase inhibitors and structurally related compounds. THEOCHEM 231:201-213. doi:10.1016/0166-1280(91) 85 218-V.
48. Erlejman AG, Verstraeten SV, Fraga CG, Oteiza PI (2004) The interaction of flavonoids with membranes: potential determinant of flavonoid antioxidant effects. Free Radic Res 38:1311-1320. doi:10.1080/10715760400016105. (Pubitemid 40045483)
49. Olivero-Verbel J, Pacheco-Londoño L (2002) Structure-Activity Relationships for The Anti-HIV Activity of Flavonoids. J Chem Inf Comput Sci 42:1241-1246. doi:10.1021/ci020363d. (Pubitemid 35360308)
50. Bonin KD, Kresin VV (1997) Electric-Dipole Polarizabilities of Atoms Molecules and Clusters. World Scientific, Singapore.
51. Foresman JB, Frisch AE (1996) Exploring Chemistry with Electronic Structure Methods. Gaussian, Pittsburgh PA, USA.
52. Lewars E (2003) Computational Chemistry-Introduction to the Theory and Applications of Molecular and Quantum Mechanics. Kluwer Academic Publishers, Norwell MA, USA.
53. Hatch FT, Lightstone FC, Colvein ME (2000) Quantitative structure-activity relationship of flavonoids for inhibition of heterocyclic amine mutagenicity. Environ Mol Mutagen 35:279-299. doi:10.1002/1098-2280(2000) 35:4<279::AID-EM3>3.0. CO;2-9.
54. Rasulev BF, Abdullaev ND, Syrov VN, Leszczynski J (2005) A quantitative structure-activity relationship (QSAR) study of the antioxidant activity of flavonoids. QSAR Combin. Sci 24:1056-1065. doi:10.1002/qsar.200430013. (Pubitemid 41736471)
55. Chaudière J, Ferrari-Iliou R (1999) Intracellular antioxidants: from chemical to biochemical mechanisms. Food Chem Toxicol 37:949-962. doi:10.1016/S0278-6915(99)00090-3. (Pubitemid 29481797)
56. Martins HFP, Fernandez MT, Lopes VHC, Cordeiro MNDS (2004) Toward the prediction of the activity of antioxidants: experimental and theoretical study of the gas-phase acidities of flavonoids. J Am Soc Mass Spectrom 15:848-861. doi:10.1016/j.jasms.2004.02.007. (Pubitemid 38624233)
57. Li MJ, Liu L, Fu Y, Guo QX (2007) Accurate bond dissociation enthalpies of popular antioxidants predicted by the ONIOM-G3B3 method. THEOCHEM 815:1-9. doi:10.1016/j.theochem.2007. 03.012.
58. Trouillas P, Marsal P, Siri D, Lazzaroni R, Duroux JL (2006) A DFT study of the reactivity of OH groups in quercetin and taxifolin antioxidants: the specificity of the 3-OH site. Food Chem 97:679-688. doi:10.1016/j.foodchem.2005. 05. 042.
59. Wolfe KL, Liu RH (2008) Structure-activity relationships of flavonoids in the cellular antioxidant activity assay. J Agric Food Chem 56:8404-8411. doi:10.1021/jf8013074.
60. Munoz-Munoz JL, Garcia-Molina F, Molina-Alarcón M, Tudela J, Carcía-Cánovas F, Rodríguez-López JN (2008) Kinetic character-ization of the enzymatic and chemical oxidation of the catechins in green tea. J Agric Food Chem 56:9215-9224. doi:10.1021/jf8012162.
61. Tsimogiannis DI, Oreopoulou V (2005) The contribution of flavonoid C-ring on the DPPH free radical scavenging efficiency. A kinetic approach for the 3′, 4′-hydroxy substituted members. Innov Food Sci Emerg Technol 7:140-146. doi:10.1016/j.ifset. 2005.09.001.
62. Wang LF, Zhang HY (2004) Unexpected role of 5-OH in DPPH radical-scavenging activity of 4-thiaflavans. Revealed by theoretical calculations. Bioorg Med Chem Lett 14:2609-2611. doi:10.1016/j.bmcl.2004.02.066. (Pubitemid 38515712)