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Volumn 25, Issue 10, 2012, Pages 2153-2166

Antioxidant activity of rooperol investigated through Cu (I and II) chelation ability and the hydrogen transfer mechanism: A DFT study

Author keywords

[No Author keywords available]

Indexed keywords

ANTIOXIDANT; COPPER COMPLEX; COPPER ION; HYDROGEN; ROOPEROL; SOLVENT; UNCLASSIFIED DRUG;

EID: 84867493542     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx300244z     Document Type: Article
Times cited : (42)

References (50)
  • 1
    • 2442492717 scopus 로고
    • Synthesis of rooperol (1,5-bis(3′,4′-dihydroxyphenyl)pent-1- en-4-yne)
    • Potgieter, M., Wenteler, G. L., and Drewes, S. E. (1988) Synthesis of rooperol (1,5-bis(3′,4′-dihydroxyphenyl)pent-1-en-4-yne) Phytochemistry 27, 1101-1104
    • (1988) Phytochemistry , vol.27 , pp. 1101-1104
    • Potgieter, M.1    Wenteler, G.L.2    Drewes, S.E.3
  • 2
    • 33947314767 scopus 로고    scopus 로고
    • Isolation, characterization and antioxidant capacity assessment of the bioactive compounds derived from Hypoxis rooperi corm extract (African potato)
    • Laporta, O., Perez-Fons, L., Mallavia, R., Caturla, N., and Micol, V. (2007) Isolation, characterization and antioxidant capacity assessment of the bioactive compounds derived from Hypoxis rooperi corm extract (African potato) Food Chem. 101, 1425-1437
    • (2007) Food Chem. , vol.101 , pp. 1425-1437
    • Laporta, O.1    Perez-Fons, L.2    Mallavia, R.3    Caturla, N.4    Micol, V.5
  • 3
    • 34447569541 scopus 로고    scopus 로고
    • In vitro evaluation of human cytochrome P450 and P-glycoprotein-mediated metabolism of some phytochemicals in extracts and formulations of African potato
    • Nair, V. D. P., Foster, B. C., Arnason, J. T., Mills, E. J., and Kanfer, I. (2007) In vitro evaluation of human cytochrome P450 and P-glycoprotein- mediated metabolism of some phytochemicals in extracts and formulations of African potato Phytomedicine 14, 498-507
    • (2007) Phytomedicine , vol.14 , pp. 498-507
    • Nair, V.D.P.1    Foster, B.C.2    Arnason, J.T.3    Mills, E.J.4    Kanfer, I.5
  • 5
    • 79952172894 scopus 로고    scopus 로고
    • Structure of dihydrochalcones and related derivatives and their scavenging and antioxidant activity against oxygen and nitrogen radical species
    • Bentes, A. L. A., Borges, R. S., Monteiro, W. R., de Macedo, L. G. M., and Alves., C. N. (2011) Structure of dihydrochalcones and related derivatives and their scavenging and antioxidant activity against oxygen and nitrogen radical species Molecules 16, 1749-1760
    • (2011) Molecules , vol.16 , pp. 1749-1760
    • Bentes, A.L.A.1    Borges, R.S.2    Monteiro, W.R.3    De MacEdo, L.G.M.4    Alves, C.N.5
  • 6
    • 1642502300 scopus 로고    scopus 로고
    • Structure, conformation and electronic properties of apigenin, luteolin and taxifolin antioxidants. A first principle theoretical study
    • Leopoldini, M., Pitarch, I. P, Russo, N., and Toscano, M. (2004) Structure, conformation and electronic properties of apigenin, luteolin and taxifolin antioxidants. A first principle theoretical study J. Phys. Chem. A 108, 92-96
    • (2004) J. Phys. Chem. A , vol.108 , pp. 92-96
    • Leopoldini, M.1    Pitarch, I.P.2    Russo, N.3    Toscano, M.4
  • 7
    • 84962429291 scopus 로고    scopus 로고
    • Antioxidant properties of phenolic compounds: H-atom versus electron transfer mechanism
    • Leopoldini, M., Marino, T., Russo, N., and Toscano, M. (2004) Antioxidant properties of phenolic compounds: H-atom versus electron transfer mechanism J. Phys. Chem. A. 108, 4916-4922
    • (2004) J. Phys. Chem. A. , vol.108 , pp. 4916-4922
    • Leopoldini, M.1    Marino, T.2    Russo, N.3    Toscano, M.4
  • 8
    • 2442417429 scopus 로고    scopus 로고
    • Density functional computations of the energetic and spectroscopic parameters of quercetin and its radicals in the gas phase and in solvent
    • Leopoldini, M., Marino, T., Russo, N., and 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
    • (2004) Theor. Chem. Acc. , vol.111 , pp. 210-216
    • Leopoldini, M.1    Marino, T.2    Russo, N.3    Toscano, M.4
  • 9
    • 0027497805 scopus 로고
    • Interaction of the dicatechols rooperol and nordihydroguaiaretic acid with oxidative systems in the human blood
    • Van der Merwe, M. J., Jenkins, K., Theron, E., and van der Walt, B. J. (1993) Interaction of the dicatechols rooperol and nordihydroguaiaretic acid with oxidative systems in the human blood Biochem. Pharmacol. 45, 303-311
    • (1993) Biochem. Pharmacol. , vol.45 , pp. 303-311
    • Van Der Merwe, M.J.1    Jenkins, K.2    Theron, E.3    Van Der Walt, B.J.4
  • 10
    • 0037027537 scopus 로고    scopus 로고
    • A DFT/ab initio study of hydrogen bonding and conformational preference in model cellobiose analogs using B3LYP/6-311++G* *
    • Strati, G. L., Willett, J. L., and Momany, F. A. (2002) A DFT/ab initio study of hydrogen bonding and conformational preference in model cellobiose analogs using B3LYP/6-311++G** Carbohydr. Res. 337, 1851-1859
    • (2002) Carbohydr. Res. , vol.337 , pp. 1851-1859
    • Strati, G.L.1    Willett, J.L.2    Momany, F.A.3
  • 12
    • 0000189651 scopus 로고
    • Density-functional thermochemistry. III. The role of exact exchange
    • Becker, A. D. (1993) Density-functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 98, 5648-5653
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648-5653
    • Becker, A.D.1
  • 13
    • 33947413134 scopus 로고    scopus 로고
    • Comparison of DFT methods for molecular orbital eigenvalue calculations
    • Zhang, G. and Musgrave, C. B. (2007) Comparison of DFT methods for molecular orbital eigenvalue calculations J. Phys. Chem. A 111, 1554-1561
    • (2007) J. Phys. Chem. A , vol.111 , pp. 1554-1561
    • Zhang, G.1    Musgrave, C.B.2
  • 14
    • 84961985248 scopus 로고    scopus 로고
    • Conformational landscape of (R, R)-Pterocarpans with biological activity in vacuo and in aqueous solution (PCM and/or water clusters)
    • Alagona, G. and Ghio, C (2006) Conformational landscape of (R, R)-Pterocarpans with biological activity in vacuo and in aqueous solution (PCM and/or water clusters) J. Phys. Chem. A 110, 647-659
    • (2006) J. Phys. Chem. A , vol.110 , pp. 647-659
    • Alagona, G.1    Ghio, C.2
  • 16
    • 0011083499 scopus 로고
    • Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint
    • Reed, A. E., Curtiss, L. A., and Weinhold, F. (1988) Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint Chem. Rev. 88, 899-926
    • (1988) Chem. Rev. , vol.88 , pp. 899-926
    • Reed, A.E.1    Curtiss, L.A.2    Weinhold, F.3
  • 18
    • 49149084741 scopus 로고    scopus 로고
    • Performance of SM8 on a test to predict small-molecule solvation free energies
    • Chamberlin, A. C., Cramer, C. J., and Truhlar, D. G. (2008) Performance of SM8 on a test to predict small-molecule solvation free energies J. Phys. Chem. B 112, 8651-8655
    • (2008) J. Phys. Chem. B , vol.112 , pp. 8651-8655
    • Chamberlin, A.C.1    Cramer, C.J.2    Truhlar, D.G.3
  • 20
    • 84961980477 scopus 로고    scopus 로고
    • Quantum mechanical continuum solvation models
    • Tomasi, J., Mennucci, B., and Cammi, R (2005) Quantum mechanical continuum solvation models Chem. ReV. 105, 2999-3093
    • (2005) Chem. ReV. , vol.105 , pp. 2999-3093
    • Tomasi, J.1    Mennucci, B.2    Cammi, R.3
  • 21
    • 0031209054 scopus 로고    scopus 로고
    • A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics
    • Cancès, E., Mennucci, B., and Tomasi, J. (1997) A new integral equation formalism for the polarizable continuum model: theoretical background and applications to isotropic and anisotropic dielectrics J. Chem. Phys. 107, 3032-3041
    • (1997) J. Chem. Phys. , vol.107 , pp. 3032-3041
    • Cancès, E.1    Mennucci, B.2    Tomasi, J.3
  • 22
    • 34247894012 scopus 로고    scopus 로고
    • DFT study of quercetin activated forms involved in antiradical, antioxidant, and prooxidant biological processes
    • Fiorucci, S. B., Golebiowski, J., Cabrol-Bass, D., and Antonczak, S. (2007) DFT study of quercetin activated forms involved in antiradical, antioxidant, and prooxidant biological processes J. Agric. Food Chem. 55, 903-911
    • (2007) J. Agric. Food Chem. , vol.55 , pp. 903-911
    • Fiorucci, S.B.1    Golebiowski, J.2    Cabrol-Bass, D.3    Antonczak, S.4
  • 23
    • 84961978597 scopus 로고    scopus 로고
    • Antioxidant properties of pterocarpans through their copper(II) coordination ability. A DFT study in vacuo and in aqueous solution
    • Alagona, G. and Ghio, C. (2009) Antioxidant properties of pterocarpans through their copper(II) coordination ability. A DFT study in vacuo and in aqueous solution J. Phys. Chem. A 113, 15206-15216
    • (2009) J. Phys. Chem. A , vol.113 , pp. 15206-15216
    • Alagona, G.1    Ghio, C.2
  • 24
    • 84962361108 scopus 로고    scopus 로고
    • Plicatin B conformational landscape and affinity to copper (I and II) metal cations. A DFT study
    • Alagona, G. and Ghio, C. (2009) Plicatin B conformational landscape and affinity to copper (I and II) metal cations. A DFT study Phys. Chem. Chem. Phys. 11, 776-790
    • (2009) Phys. Chem. Chem. Phys. , vol.11 , pp. 776-790
    • Alagona, G.1    Ghio, C.2
  • 26
    • 84861659189 scopus 로고    scopus 로고
    • On the prediction of OH stretching frequencies in intramolecularly hydrogen bonded systems
    • Hansen, P. E. and Spanget-Larsen, J. (2012) On the prediction of OH stretching frequencies in intramolecularly hydrogen bonded systems J. Mol. Struct. 1018, 8-13
    • (2012) J. Mol. Struct. , vol.1018 , pp. 8-13
    • Hansen, P.E.1    Spanget-Larsen, J.2
  • 27
    • 73949121435 scopus 로고    scopus 로고
    • A computational study of the effects of different solvents on the characteristics of the intramolecular hydrogen bond in acylphloroglucinols
    • Mammino, L. and Kabanda, M. M. (2009) A computational study of the effects of different solvents on the characteristics of the intramolecular hydrogen bond in acylphloroglucinols J. Phys. Chem. A 113, 15064-15077
    • (2009) J. Phys. Chem. A , vol.113 , pp. 15064-15077
    • Mammino, L.1    Kabanda, M.M.2
  • 28
    • 4243585088 scopus 로고
    • Chemical reactivity and the concept of charge- and frontier-controlled reactions
    • Klopman, G. (1968) Chemical reactivity and the concept of charge- and frontier-controlled reactions J. Am. Chem. Soc. 90, 223-234
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 223-234
    • Klopman, G.1
  • 30
    • 0033860031 scopus 로고    scopus 로고
    • Semiempirical molecular modeling into quercetin reactive site: Structural, conformational, and electronic features
    • Russo, N., Toscano, M., and Uccella, N. (2000) Semiempirical molecular modeling into quercetin reactive site: structural, conformational, and electronic features J. Agric. Food Chem. 48, 3232-3237
    • (2000) J. Agric. Food Chem. , vol.48 , pp. 3232-3237
    • Russo, N.1    Toscano, M.2    Uccella, N.3
  • 31
    • 0035857407 scopus 로고    scopus 로고
    • Predicting the activity of phenolic antioxidants: Theoretical method, analysis of substituent effects, and application to major families of antioxidants
    • Wright, J. S., Jonhson, E. R., and DiLabio, G. A. (2001) Predicting the activity of phenolic antioxidants: theoretical method, analysis of substituent effects, and application to major families of antioxidants J. Am. Chem. Soc. 123, 1173-1183
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 1173-1183
    • Wright, J.S.1    Jonhson, E.R.2    Dilabio, G.A.3
  • 32
    • 31844444029 scopus 로고    scopus 로고
    • A DFT study of the reactivity of OH groups in quercetin and taxifolin antioxidants: The specificity of the 3-OH site
    • Trouillas, P., Marsal, P., Siri, D., Lazzaroni, R., and Duroux, J.-L. (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
    • (2006) Food Chem. , vol.97 , pp. 679-688
    • Trouillas, P.1    Marsal, P.2    Siri, D.3    Lazzaroni, R.4    Duroux, J.-L.5
  • 33
    • 33847372916 scopus 로고    scopus 로고
    • Density functional theory study of the conformational, electronic, and antioxidant properties of natural chalcones
    • Kozlowski, D., Trouillas, P., Calliste, C., Marsal, P., Lazzaroni, R., and Duroux, J. L. (2007) Density functional theory study of the conformational, electronic, and antioxidant properties of natural chalcones J. Phys. Chem. A 111, 1138-1145
    • (2007) J. Phys. Chem. A , vol.111 , pp. 1138-1145
    • Kozlowski, D.1    Trouillas, P.2    Calliste, C.3    Marsal, P.4    Lazzaroni, R.5    Duroux, J.L.6
  • 34
    • 0037067554 scopus 로고    scopus 로고
    • Determination of the substituent effect on the O-H bond dissociation enthalpies of phenolic antioxidants by the EPR radical equilibration technique
    • Brigati, G., Lucarini, M., Mugnaini, V., and Pedulli, G. F. (2002) Determination of the substituent effect on the O-H bond dissociation enthalpies of phenolic antioxidants by the EPR radical equilibration technique J. Org. Chem. 67, 4828-4832
    • (2002) J. Org. Chem. , vol.67 , pp. 4828-4832
    • Brigati, G.1    Lucarini, M.2    Mugnaini, V.3    Pedulli, G.F.4
  • 35
    • 84875250368 scopus 로고    scopus 로고
    • Standard enthalpies of formation of 2,6-di-tert-butyl-4-methylphenol and 3,5-di-tert-butylphenol and their phenoxy radicals
    • Santos, R. M. B. and Simões, J. A. M. (1998) Standard enthalpies of formation of 2,6-di-tert-butyl-4-methylphenol and 3,5-di-tert-butylphenol and their phenoxy radicals J. Phys. Chem. Ref. Data 27, 707-741
    • (1998) J. Phys. Chem. Ref. Data , vol.27 , pp. 707-741
    • Santos, R.M.B.1    Simões, J.A.M.2
  • 36
    • 24644495344 scopus 로고    scopus 로고
    • Reduction potentials of flavonoid and model phenoxyl radicals. Which ring in flavonoids is responsible for antioxidant activity?
    • Jovanovic, S. V., Steenken, S., Hara, Y., and Simic, M. G. (1996) Reduction potentials of flavonoid and model phenoxyl radicals. Which ring in flavonoids is responsible for antioxidant activity? J. Chem. Soc., Perkin Trans. 2, 2497-2504
    • (1996) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 2497-2504
    • Jovanovic, S.V.1    Steenken, S.2    Hara, Y.3    Simic, M.G.4
  • 38
    • 1942534239 scopus 로고    scopus 로고
    • Unexpected role of 5-OH in DPPH radical-scavenging activity of 4-thiaflavans
    • Wang, L. F. and Zang, H. Y. (2004) Unexpected role of 5-OH in DPPH radical-scavenging activity of 4-thiaflavans Bioorg. Med. Chem. Lett. 14, 2609-2611
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 2609-2611
    • Wang, L.F.1    Zang, H.Y.2
  • 39
  • 40
    • 0042282065 scopus 로고    scopus 로고
    • Assessment of theoretical procedures for the calculation of reliable radical stabilization energies
    • Parkinson, C. J., Mayer, P. M., and Radom, L. (1999) Assessment of theoretical procedures for the calculation of reliable radical stabilization energies J. Chem. Soc., Perkin Trans. 2 11, 2305-2313
    • (1999) J. Chem. Soc., Perkin Trans. 2 , vol.11 , pp. 2305-2313
    • Parkinson, C.J.1    Mayer, P.M.2    Radom, L.3
  • 41
    • 72049086021 scopus 로고    scopus 로고
    • Reliability of bond dissociation enthalpy calculated by the PM6 method and experimental TEAC values in antiradical QSAR of flavonoids
    • Amic, D. and Lucić, B. (2010) Reliability of bond dissociation enthalpy calculated by the PM6 method and experimental TEAC values in antiradical QSAR of flavonoids Bioorg. Med. Chem. 18, 28-35
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 28-35
    • Amic, D.1    Lucić, B.2
  • 42
    • 38149007776 scopus 로고    scopus 로고
    • Chemical reactivities and physical effects in comparison between tocopherols and tocotrienols: Physiological significance and prospects as antioxidants
    • Yoshida, Y., Saito, Y., Jones, L. S., and Shigeri, Y. (2007) Chemical reactivities and physical effects in comparison between tocopherols and tocotrienols: physiological significance and prospects as antioxidants J. Biosci. Bioeng. 104, 439-445
    • (2007) J. Biosci. Bioeng. , vol.104 , pp. 439-445
    • Yoshida, Y.1    Saito, Y.2    Jones, L.S.3    Shigeri, Y.4
  • 43
    • 0023902307 scopus 로고
    • Interaction of α-tocopherol with iron: Antioxidant and prooxidant effects of α-tocopherol in the oxidation of lipids in aqueous dispersions in the presence of iron
    • Yamamoto, K. and Niki, E. (1988) Interaction of α-tocopherol with iron: antioxidant and prooxidant effects of α-tocopherol in the oxidation of lipids in aqueous dispersions in the presence of iron Biochim. Biophys. Acta 958, 19-23
    • (1988) Biochim. Biophys. Acta , vol.958 , pp. 19-23
    • Yamamoto, K.1    Niki, E.2
  • 44
    • 0028177270 scopus 로고
    • Interaction of α-tocopherol with copper and its effect on lipid peroxidation
    • Yoshida, Y., Tsuchiya, J., and Niki, E. (1994) Interaction of α-tocopherol with copper and its effect on lipid peroxidation Biochim. Biophys. Acta 1200, 85-92
    • (1994) Biochim. Biophys. Acta , vol.1200 , pp. 85-92
    • Yoshida, Y.1    Tsuchiya, J.2    Niki, E.3
  • 45
    • 0027199367 scopus 로고
    • Prooxidant role of vitamin e in copper induced lipid peroxidation
    • Maiorino, M., Zamburlini, A., Roveri, A., and Ursini, F. (1993) Prooxidant role of vitamin E in copper induced lipid peroxidation FEBS Lett. 330, 174-176
    • (1993) FEBS Lett. , vol.330 , pp. 174-176
    • Maiorino, M.1    Zamburlini, A.2    Roveri, A.3    Ursini, F.4
  • 46
    • 0028813586 scopus 로고
    • Copper-induced lipid peroxidation in liposomes, micelles, and LDL: Which is the role of vitamin-E?
    • Maiorino, M., Zamburlini, A., Roveri, A., and Ursini, F. (1995) Copper-induced lipid peroxidation in liposomes, micelles, and LDL: which is the role of vitamin-E? Free Radical Biol. Med. 18, 67-74
    • (1995) Free Radical Biol. Med. , vol.18 , pp. 67-74
    • Maiorino, M.1    Zamburlini, A.2    Roveri, A.3    Ursini, F.4
  • 47
    • 0030011080 scopus 로고    scopus 로고
    • α-tocopherol as a reductant for Cu(II) in human lipoproteins: Triggering role in the initiation of lipoprotein oxidation
    • Kontush, A., Meyer, S., Finckh, B., Kohlschutter, A., and Beisiegel, U. (1996) α-tocopherol as a reductant for Cu(II) in human lipoproteins: triggering role in the initiation of lipoprotein oxidation J. Biol. Chem. 271, 11106-11112
    • (1996) J. Biol. Chem. , vol.271 , pp. 11106-11112
    • Kontush, A.1    Meyer, S.2    Finckh, B.3    Kohlschutter, A.4    Beisiegel, U.5
  • 48
    • 0036008313 scopus 로고    scopus 로고
    • Copper-induced peroxidation of liposomal palmitoyllinoleoylphosphatidylcholine (PLPC), effect of antioxidants and its dependence on the oxidative stress
    • Bittner, O., Gal, S., Pinchuk, I., Danino, D., Shinar, H., and Lichtenberg, D. (2002) Copper-induced peroxidation of liposomal palmitoyllinoleoylphosphatidylcholine (PLPC), effect of antioxidants and its dependence on the oxidative stress Chem. Phys. Lipids 114, 81-98
    • (2002) Chem. Phys. Lipids , vol.114 , pp. 81-98
    • Bittner, O.1    Gal, S.2    Pinchuk, I.3    Danino, D.4    Shinar, H.5    Lichtenberg, D.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.