메뉴 건너뛰기




Volumn 58, Issue 15, 2010, Pages 8862-8871

Pyranoanthocyanins: A theoretical investigation on their antioxidant activity

Author keywords

Anthocyanins; BDE; density functional; IP; pigments; wine aging

Indexed keywords

ANTIOXIDANT ACTIVITIES; BDE; BENZENE SOLUTION; CHEMICAL TRANSFORMATIONS; DENSITY FUNCTIONALS; ELECTRON DELOCALIZATION; GASPHASE; HEALTH EFFECTS; HIGHER-DEGREE; IP; MOLECULAR INSIGHTS; O-H BOND; RADICAL SCAVENGING; SINGLE ELECTRON TRANSFER; SYSTEMS POSSESSING; THEORETICAL INVESTIGATIONS; WINE AGING; WORKING MECHANISMS;

EID: 77955689685     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf101693k     Document Type: Article
Times cited : (104)

References (58)
  • 1
    • 0036400016 scopus 로고    scopus 로고
    • Dietary flavonoids: Bioavailability, metabolic effects, and safety
    • Ross, J. A.; Kasum, C. M. Dietary flavonoids: bioavailability, metabolic effects, and safety Annu. Rev. Nutr 2002, 22, 19-34
    • (2002) Annu. Rev. Nutr , vol.22 , pp. 19-34
    • Ross, J.A.1    Kasum, C.M.2
  • 2
    • 0027291905 scopus 로고
    • Intake of potentially anticarcinogenic flavonoids and their determinants in adults in the Netherlands
    • Hertog, M. G. L.; Hollman, P. C. H.; Katan, M. B.; Kromhout, D. Intake of potentially anticarcinogenic flavonoids and their determinants in adults in the Netherlands Nutr. Cancer 1993, 20, 21-29
    • (1993) Nutr. Cancer , vol.20 , pp. 21-29
    • Hertog, M.G.L.1    Hollman, P.C.H.2    Katan, M.B.3    Kromhout, D.4
  • 3
    • 0034807826 scopus 로고    scopus 로고
    • Dietary agents in cancer prevention: Flavonoids and isoflavonoids
    • Brit, D. F.; Hendrich, S.; Wang, W. Dietary agents in cancer prevention: flavonoids and isoflavonoids Pharmacol. Ther. 2001, 90, 157-177
    • (2001) Pharmacol. Ther. , vol.90 , pp. 157-177
    • Brit, D.F.1    Hendrich, S.2    Wang, W.3
  • 7
    • 0032989507 scopus 로고    scopus 로고
    • Chlorogenic acids and other cinnamates-nature, occurence and dietary burden
    • Clifford, M. N. Chlorogenic acids and other cinnamates-nature, occurence and dietary burden J. Sci. Food Agric. 1999, 79, 362-372
    • (1999) J. Sci. Food Agric. , vol.79 , pp. 362-372
    • Clifford, M.N.1
  • 9
    • 0342423850 scopus 로고
    • Flavonoid antioxidants in food of plant origin
    • Hermann, K. Flavonoid antioxidants in food of plant origin Gordian 1993, 7′8) 108-111
    • (1993) Gordian , Issue.7-8 , pp. 108-111
    • Hermann, K.1
  • 10
    • 0026651085 scopus 로고
    • Wine, alcohol, platelets, and the French paradox for coronary heart disease
    • Renaud, S.; De Lorgeril, M. Wine, alcohol, platelets, and the French paradox for coronary heart disease Lancet 1992, 339, 1523-1526
    • (1992) Lancet , vol.339 , pp. 1523-1526
    • Renaud, S.1    De Lorgeril, M.2
  • 11
    • 0027396786 scopus 로고
    • Inhibition of oxidation of human low-density lipoprotein by phenolic substances in red wine
    • Frankel, E. N.; Kanner, J.; German, J. B.; Parks, E.; Kinsella, J. E. Inhibition of oxidation of human low-density lipoprotein by phenolic substances in red wine Lancet 1993, 341, 454-457
    • (1993) Lancet , vol.341 , pp. 454-457
    • Frankel, E.N.1    Kanner, J.2    German, J.B.3    Parks, E.4    Kinsella, J.E.5
  • 12
    • 0027504187 scopus 로고
    • Dietary antioxidative flavonoids and risk of coronary heart disease: The Zutphen Elderly Study
    • Hertog, M. G. L.; Freskens, E. J. M.; Hollman, P. C. H.; Katan, M. B.; Kromhout, D. Dietary antioxidative flavonoids and risk of coronary heart disease: the Zutphen Elderly Study Lancet 1993, 342, 1007-1011
    • (1993) Lancet , vol.342 , pp. 1007-1011
    • Hertog, M.G.L.1    Freskens, E.J.M.2    Hollman, P.C.H.3    Katan, M.B.4    Kromhout, D.5
  • 13
    • 0038408778 scopus 로고    scopus 로고
    • Phenolic acids in foods: An overview of analytical methodology
    • Robbins, R. J. Phenolic acids in foods: an overview of analytical methodology J. Agric. Food Chem. 2003, 51, 2866-2887
    • (2003) J. Agric. Food Chem. , vol.51 , pp. 2866-2887
    • Robbins, R.J.1
  • 14
    • 0032984234 scopus 로고    scopus 로고
    • Characteristics and occurrence of phenolic phytochemicals
    • King, A.; Young, G. Characteristics and occurrence of phenolic phytochemicals J. Am. Diet. Assoc. 1999, 99, 213-218
    • (1999) J. Am. Diet. Assoc. , vol.99 , pp. 213-218
    • King, A.1    Young, G.2
  • 15
    • 0000282145 scopus 로고
    • Anthocyanins
    • Harborne, J. B., Ed. Academic Press: London, U.K.
    • Strack, D.; Wray, V. Anthocyanins. In Methods in Plant Biochemistry, Plant Phenolics; Harborne, J. B., Ed.; Academic Press: London, U.K., 1993; Vol. 1, pp 325-356.
    • (1993) Methods in Plant Biochemistry, Plant Phenolics , vol.1 , pp. 325-356
    • Strack, D.1    Wray, V.2
  • 16
    • 0346433433 scopus 로고    scopus 로고
    • Functional properties of anthocyanins and betalins in plants, food, and in human nutrition
    • Stinzing, F. C.; Carle, R. Functional properties of anthocyanins and betalins in plants, food, and in human nutrition Trends Food Sci. Technol. 2004, 15, 19-38
    • (2004) Trends Food Sci. Technol. , vol.15 , pp. 19-38
    • Stinzing, F.C.1    Carle, R.2
  • 17
    • 12844281857 scopus 로고    scopus 로고
    • Human tumor cell growth inhibition by nontoxic anthocyanidins, the pigments in fruits and vegetables
    • Zhang, Y.; Vareed, S. K.; Nair, M. G. Human tumor cell growth inhibition by nontoxic anthocyanidins, the pigments in fruits and vegetables Life Sci. 2005, 76, 1465-1472
    • (2005) Life Sci. , vol.76 , pp. 1465-1472
    • Zhang, Y.1    Vareed, S.K.2    Nair, M.G.3
  • 18
    • 11244279678 scopus 로고    scopus 로고
    • Insulin secretion by bioactive anthocyanins and anthocyanidins present in fruits
    • Jayaprakasam, B.; Vareed, S. K.; Olson, L. K.; Nair, M. G. Insulin secretion by bioactive anthocyanins and anthocyanidins present in fruits J. Agric. Food Chem. 2005, 53, 28-31
    • (2005) J. Agric. Food Chem. , vol.53 , pp. 28-31
    • Jayaprakasam, B.1    Vareed, S.K.2    Olson, L.K.3    Nair, M.G.4
  • 19
    • 0034861322 scopus 로고    scopus 로고
    • α-glucosidase inhibitory action of natural acylated anthocyanins. 1. Survey of natural pigments with potent inhibitory activity
    • DOI 10.1021/jf001251u
    • Matsui, T.; Ueda, T.; Oki, T.; Sugita, K.; Terahara, N.; Matsumoto, K. α-Glucosidase inhibitory action of natural acylated anthocyanins. 1. Survey of natural pigments with potent inhibitory activity J. Agric. Food Chem. 2001, 49, 1948-1951 (Pubitemid 32816843)
    • (2001) Journal of Agricultural and Food Chemistry , vol.49 , Issue.4 , pp. 1948-1951
    • Matsui, T.1    Ueda, T.2    Oki, T.3    Sugita, K.4    Terahara, N.5    Matsumoto, K.6
  • 21
    • 0141449748 scopus 로고    scopus 로고
    • Effect of different oak woods on aged wine color and anthocyanin composition
    • Revilla, I.; González-SanJosé, M. L. Effect of different oak woods on aged wine color and anthocyanin composition Eur. Food Res. Technol. 2001, 213, 281-285
    • (2001) Eur. Food Res. Technol. , vol.213 , pp. 281-285
    • Revilla, I.1    González-Sanjosé, M.L.2
  • 22
    • 0345305322 scopus 로고    scopus 로고
    • Why are grape/fresh wine anthocyanins so simple and why is it that red wine color lasts so long?
    • Brouillard, R.; Chassaing, S.; Fougerousse, A. Why are grape/fresh wine anthocyanins so simple and why is it that red wine color lasts so long? Phytochemistry 2003, 64, 1179-1186
    • (2003) Phytochemistry , vol.64 , pp. 1179-1186
    • Brouillard, R.1    Chassaing, S.2    Fougerousse, A.3
  • 23
    • 0000727430 scopus 로고
    • The polymeric nature of wine pigments
    • Somers, T. C. The polymeric nature of wine pigments Phytochemistry 1971, 10, 2175-2186
    • (1971) Phytochemistry , vol.10 , pp. 2175-2186
    • Somers, T.C.1
  • 24
    • 0000413672 scopus 로고
    • Review of polyphenol condensation reactions and their possible occurrence in the aging of wines
    • Jurd, L. Review of polyphenol condensation reactions and their possible occurrence in the aging of wines Am. J. Enol. Vitic. 1969, 20, 191-195
    • (1969) Am. J. Enol. Vitic. , vol.20 , pp. 191-195
    • Jurd, L.1
  • 25
    • 0343487438 scopus 로고
    • Polyphenol interactions. Anthocyanins: Copigmentation and colour changes in red wines
    • Liao, H.; Cai, Y.; Haslam, E. Polyphenol interactions. Anthocyanins: copigmentation and colour changes in red wines J. Sci. Food Agric. 1992, 59, 299-305
    • (1992) J. Sci. Food Agric. , vol.59 , pp. 299-305
    • Liao, H.1    Cai, Y.2    Haslam, E.3
  • 26
    • 0034193605 scopus 로고    scopus 로고
    • First confirmation in red wine of products resulting from direct anthocyanin-tannin reactions
    • Remy, S.; Fulcrand, H.; Labarbe, B.; Cheynier, V.; Moutounet, M. First confirmation in red wine of products resulting from direct anthocyanin-tannin reactions J. Sci. Food Agric. 2000, 80, 745-751
    • (2000) J. Sci. Food Agric. , vol.80 , pp. 745-751
    • Remy, S.1    Fulcrand, H.2    Labarbe, B.3    Cheynier, V.4    Moutounet, M.5
  • 27
    • 0001020559 scopus 로고
    • Model wine solutions: Colour and composition changes during ageing
    • Bakker, J.; Picinelli, A.; Bridle, P. Model wine solutions: colour and composition changes during ageing Vitis 1993, 32, 111-118
    • (1993) Vitis , vol.32 , pp. 111-118
    • Bakker, J.1    Picinelli, A.2    Bridle, P.3
  • 28
    • 0000648611 scopus 로고
    • Detection of compounds formed through the reaction of malvidin-3-monoglucoside and catechin in the presence of acetaldehyde
    • Rivas-Gonzalo, J. C.; Bravo-Haro, S.; Santos-Buelga, C. Detection of compounds formed through the reaction of malvidin-3-monoglucoside and catechin in the presence of acetaldehyde J. Agric. Food Chem. 1995, 43, 1444-1449
    • (1995) J. Agric. Food Chem. , vol.43 , pp. 1444-1449
    • Rivas-Gonzalo, J.C.1    Bravo-Haro, S.2    Santos-Buelga, C.3
  • 29
    • 0001940873 scopus 로고
    • Interactions between anthocyanins, phenolics compounds and acetaldehyde, and their significance in red wines
    • Timberlake, C. F.; Bridle, P. Interactions between anthocyanins, phenolics compounds and acetaldehyde, and their significance in red wines Am. J. Enol. Vitic. 1976, 27, 97-105
    • (1976) Am. J. Enol. Vitic. , vol.27 , pp. 97-105
    • Timberlake, C.F.1    Bridle, P.2
  • 31
    • 0001805602 scopus 로고    scopus 로고
    • Isolation, identification, and characterization of new color-stable anthocyanins occurring in some red wines
    • Bakker, J.; Timberlake, C. F. Isolation, identification, and characterization of new color-stable anthocyanins occurring in some red wines J. Agric. Food Chem. 1997, 45, 35-43
    • (1997) J. Agric. Food Chem. , vol.45 , pp. 35-43
    • Bakker, J.1    Timberlake, C.F.2
  • 32
    • 0032051861 scopus 로고    scopus 로고
    • A new class of wine pigments generated by reaction between pyruvic acid and grape anthocyanins
    • Fulcrand, H.; Benabdeljalil, C.; Rigaud, J.; Cheynier, V.; Moutounet, M. A new class of wine pigments generated by reaction between pyruvic acid and grape anthocyanins Phytochemistry 1998, 47, 1401-1407
    • (1998) Phytochemistry , vol.47 , pp. 1401-1407
    • Fulcrand, H.1    Benabdeljalil, C.2    Rigaud, J.3    Cheynier, V.4    Moutounet, M.5
  • 33
    • 0032831181 scopus 로고    scopus 로고
    • Interactions between grape anthocyanins and pyruvic acid, with effect of pH and acid concentration on anthocyanin composition and color in model solutions
    • Romero, C.; Bakker, J. Interactions between grape anthocyanins and pyruvic acid, with effect of pH and acid concentration on anthocyanin composition and color in model solutions J. Agric. Food Chem. 1999, 47, 3130-3139
    • (1999) J. Agric. Food Chem. , vol.47 , pp. 3130-3139
    • Romero, C.1    Bakker, J.2
  • 35
    • 0035187962 scopus 로고    scopus 로고
    • Evolution and stability of anthocyanin-derived pigments during Port wine aging
    • Mateus, N.; De Freitas, V. Evolution and stability of anthocyanin-derived pigments during Port wine aging J. Agric. Food Chem. 2001, 49, 5217-5222
    • (2001) J. Agric. Food Chem. , vol.49 , pp. 5217-5222
    • Mateus, N.1    De Freitas, V.2
  • 38
    • 0038012773 scopus 로고    scopus 로고
    • Pathway leading to the formation of anthocyaninvinylphenol adducts and related pigments in red wines
    • Schwarz, M.; Wabnitz, T. C.; Winterhalter, P. Pathway leading to the formation of anthocyaninvinylphenol adducts and related pigments in red wines J. Agric. Food Chem. 2003, 51, 3682-3687
    • (2003) J. Agric. Food Chem. , vol.51 , pp. 3682-3687
    • Schwarz, M.1    Wabnitz, T.C.2    Winterhalter, P.3
  • 39
    • 0034386092 scopus 로고    scopus 로고
    • Mise en evidence de nouveaux pigments formes par reaction des anthocyanes avec des metabolites de levures
    • Benabdeljalil, C.; Cheynier, V.; Fulcrand, H.; Hakiki, A.; Mosaddak, M.; Moutounet, M. Mise en evidence de nouveaux pigments formes par reaction des anthocyanes avec des metabolites de levures Sci. Aliments. 2000, 20, 203-220
    • (2000) Sci. Aliments. , vol.20 , pp. 203-220
    • Benabdeljalil, C.1    Cheynier, V.2    Fulcrand, H.3    Hakiki, A.4    Mosaddak, M.5    Moutounet, M.6
  • 40
    • 0035847560 scopus 로고    scopus 로고
    • Unusual anthocyanin reaction with acetone leading to pyranoanthocyanin formation
    • Lu, Y.; Foo, L. Y. Unusual anthocyanin reaction with acetone leading to pyranoanthocyanin formation Tetrahedron Lett. 2001, 42, 1371-1373
    • (2001) Tetrahedron Lett. , vol.42 , pp. 1371-1373
    • Lu, Y.1    Foo, L.Y.2
  • 41
    • 0037070049 scopus 로고    scopus 로고
    • Screening for potential pigments derived from anthocyanins in red wine using nanoelectrospray tandem mass spectrometry
    • Hayasaka, Y.; Asenstorfer, R. E. Screening for potential pigments derived from anthocyanins in red wine using nanoelectrospray tandem mass spectrometry J. Agric. Food Chem. 2002, 50, 756-761
    • (2002) J. Agric. Food Chem. , vol.50 , pp. 756-761
    • Hayasaka, Y.1    Asenstorfer, R.E.2
  • 42
    • 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.; Johnson, E. R.; Di Labio, G. A. Predicting the activity of phenolic antioxidants: theoretical method, analysis of substituent effects and application to major families of antioxidants J. Am. Chem. Soc. 2001, 123, 1173-1183
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 1173-1183
    • Wright, J.S.1    Johnson, E.R.2    Di Labio, G.A.3
  • 43
    • 1642502300 scopus 로고    scopus 로고
    • Structure, conformation and electronic properties of apigenin, luteolin and taxifolin antioxidants. A first principle theoretical study
    • Leopoldini, M.; Prieto Pitarch, I.; Russo, N.; Toscano, M. Structure, conformation and electronic properties of apigenin, luteolin and taxifolin antioxidants. A first principle theoretical study J. Phys. Chem. B 2004, 108, 92-94
    • (2004) J. Phys. Chem. B , vol.108 , pp. 92-94
    • Leopoldini, M.1    Prieto Pitarch, I.2    Russo, N.3    Toscano, M.4
  • 44
    • 84962429291 scopus 로고    scopus 로고
    • Antioxidant properties of phenolic compounds. H-atom versus electron transfer mechanism
    • Leopoldini, M.; Marino, T.; Russo, N.; Toscano, M. Antioxidant properties of phenolic compounds. H-atom versus electron transfer mechanism J. Phys. Chem. B 2004, 108, 4916-4922
    • (2004) J. Phys. Chem. B , vol.108 , pp. 4916-4922
    • Leopoldini, M.1    Marino, T.2    Russo, N.3    Toscano, M.4
  • 45
    • 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.; Toscano, M. Density functional computations of the energetic and spectroscopic parameters of quercetin and its radicals in the gas phase and in solvent Theor. Chem. Acc. 2004, 111, 210-216
    • (2004) Theor. Chem. Acc. , vol.111 , pp. 210-216
    • Leopoldini, M.1    Marino, T.2    Russo, N.3    Toscano, M.4
  • 46
    • 84961979266 scopus 로고    scopus 로고
    • Iron chelation by the powerful antioxidant flavonoid quercetin
    • Leopoldini, M.; Russo, N.; Chiodo, S.; Toscano, M. Iron chelation by the powerful antioxidant flavonoid quercetin J. Agric. Food Chem. 2006, 54, 6343-6351
    • (2006) J. Agric. Food Chem. , vol.54 , pp. 6343-6351
    • Leopoldini, M.1    Russo, N.2    Chiodo, S.3    Toscano, M.4
  • 47
    • 28244501048 scopus 로고    scopus 로고
    • Computational ands characterization of the molecular and electronic structure of the Pb(II)-quercetin complex
    • Cornard, J. P.; Dangleterre, L.; Lapouge, C. Computational ands characterization of the molecular and electronic structure of the Pb(II)-quercetin complex J. Phys. Chem. A 2005, 109, 10044-10051
    • (2005) J. Phys. Chem. A , vol.109 , pp. 10044-10051
    • Cornard, J.P.1    Dangleterre, L.2    Lapouge, C.3
  • 48
    • 0037201690 scopus 로고    scopus 로고
    • Spectroscopic and structural study of complexes of quercetin with Al(III)
    • Cornard, J. P.; Merlin, J. C. Spectroscopic and structural study of complexes of quercetin with Al(III) J. Inorg. Biochem. 2002, 92, 19-27
    • (2002) J. Inorg. Biochem. , vol.92 , pp. 19-27
    • Cornard, J.P.1    Merlin, J.C.2
  • 49
    • 34247894012 scopus 로고    scopus 로고
    • DFT study of quercetin activated forms involved in antiradical, antioxidant, and prooxidant biological processes
    • Fiorucci, S.; Golebiowski, J.; Cabrol-Bass, D.; Antonczak, S. DFT study of quercetin activated forms involved in antiradical, antioxidant, and prooxidant biological processes J. Agric. Food Chem. 2007, 55, 903-911
    • (2007) J. Agric. Food Chem. , vol.55 , pp. 903-911
    • Fiorucci, S.1    Golebiowski, J.2    Cabrol-Bass, D.3    Antonczak, S.4
  • 51
    • 21644480837 scopus 로고    scopus 로고
    • A DFT investigation of anthocyanidins
    • Woodford, J. A DFT investigation of anthocyanidins Chem. Phys. Lett. 2005, 410, 182-187
    • (2005) Chem. Phys. Lett. , vol.410 , pp. 182-187
    • Woodford, J.1
  • 54
    • 33644992903 scopus 로고    scopus 로고
    • Ab initio study of molecular structures and excited states in anthocyanins
    • Sakata, K.; Saito, N.; Honda, T. Ab initio study of molecular structures and excited states in anthocyanins Tetrahedron 2006, 62, 372-3731
    • (2006) Tetrahedron , vol.62 , pp. 372-3731
    • Sakata, K.1    Saito, N.2    Honda, T.3
  • 55
    • 69749115870 scopus 로고    scopus 로고
    • A density functional study of antioxidant properties on anthocyanidins
    • Guzmán, R.; Santiago, C.; Sánchez, M. A density functional study of antioxidant properties on anthocyanidins J. Mol. Struct. (THEOCHEM) 2009, 935, 110-114
    • (2009) J. Mol. Struct. (THEOCHEM) , vol.935 , pp. 110-114
    • Guzmán, R.1    Santiago, C.2    Sánchez, M.3
  • 56
    • 84966478749 scopus 로고    scopus 로고
    • Conformational and substitution effects on the electron distribution in a series of anthocyanidins
    • Estevez, L.; Mosquera, R. A. Conformational and substitution effects on the electron distribution in a series of anthocyanidins J. Phys. Chem. A 2009, 113, 9908-9919
    • (2009) J. Phys. Chem. A , vol.113 , pp. 9908-9919
    • Estevez, L.1    Mosquera, R.A.2
  • 58
    • 55649087728 scopus 로고    scopus 로고
    • Molecular structure and antioxidant properties of delphinidin
    • Estevez, L.; Mosquera, R. A. Molecular structure and antioxidant properties of delphinidin J. Phys. Chem. A 2008, 112, 10614-10623
    • (2008) J. Phys. Chem. A , vol.112 , pp. 10614-10623
    • Estevez, L.1    Mosquera, R.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.