메뉴 건너뛰기




Volumn 73, Issue 1, 1999, Pages 247-253

Inhibition of peroxynitrite-mediated oxidation of dopamine by flavonoid and phenolic antioxidants and their structural relationships

Author keywords

Caffeic acid; Catechin; Dopamine; Ferulic acid; Nitration; Oxidation; Peroxynitrite

Indexed keywords

CAFFEIC ACID; CATECHIN; COUMARIC ACID; DOPAMINE; FERULIC ACID; PEROXYNITRITE; TYROSINE;

EID: 0033026003     PISSN: 00223042     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1471-4159.1999.0730247.x     Document Type: Article
Times cited : (106)

References (40)
  • 1
    • 0030888919 scopus 로고    scopus 로고
    • Upregulation of protein-tyrosine nitration in the anterior horn cells of amyotrophic lateral sclerosis
    • Abe K., Pan L. H., Watanabe M., Konno H., Kato T., and Hoyama Y. (1997) Upregulation of protein-tyrosine nitration in the anterior horn cells of amyotrophic lateral sclerosis. Neurol. Lett. 19, 124-128.
    • (1997) Neurol. Lett. , vol.19 , pp. 124-128
    • Abe, K.1    Pan, L.H.2    Watanabe, M.3    Konno, H.4    Kato, T.5    Hoyama, Y.6
  • 2
    • 0003163908 scopus 로고    scopus 로고
    • Oxidative damage in neurodegenerative disease
    • Beal M. F. (1997) Oxidative damage in neurodegenerative disease. Neuroscience 3, 21-27.
    • (1997) Neuroscience , vol.3 , pp. 21-27
    • Beal, M.F.1
  • 4
    • 0023555979 scopus 로고
    • Radical scavenging by flavonoid antioxidants
    • Bors W. and Saran M. (1987) Radical scavenging by flavonoid antioxidants. Free Radic. Res. Commun. 2, 289-294.
    • (1987) Free Radic. Res. Commun. , vol.2 , pp. 289-294
    • Bors, W.1    Saran, M.2
  • 5
    • 0031408722 scopus 로고    scopus 로고
    • Oxidation and nitration of catecholamines by nitrogen oxides derived from nitric oxide
    • Daveu C., Servy C., Dendane M., Marin P., and Ducrocq C. (1997) Oxidation and nitration of catecholamines by nitrogen oxides derived from nitric oxide. Nitric Oxide: Biol. Chem. 1, 234-243.
    • (1997) Nitric Oxide: Biol. Chem. , vol.1 , pp. 234-243
    • Daveu, C.1    Servy, C.2    Dendane, M.3    Marin, P.4    Ducrocq, C.5
  • 6
    • 0028093156 scopus 로고
    • Nitration of catecholamines with nitrogen oxides in mild conditions
    • de la Breteche M.-L., Servy C., Lenfant M., and Ducrocq C. (1994) Nitration of catecholamines with nitrogen oxides in mild conditions. Tetrahedron Lett. 35, 7231-7232.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 7231-7232
    • De La Breteche, M.-L.1    Servy, C.2    Lenfant, M.3    Ducrocq, C.4
  • 7
  • 8
    • 0029037380 scopus 로고
    • Nitric oxide induced nitration of catecholamine neurotransmitters: A key to neuronal degeneration
    • d'Ischia M. and Costantini C. (1995) Nitric oxide induced nitration of catecholamine neurotransmitters: a key to neuronal degeneration. Bioorg. Med. Chem. 3, 923-927.
    • (1995) Bioorg. Med. Chem. , vol.3 , pp. 923-927
    • D'Ischia, M.1    Costantini, C.2
  • 9
    • 0026059789 scopus 로고
    • Vitamin C deficiency facilitates 5-S-cysteinyldopamine formation in guinea pig striatum
    • Fornstedt B. and Carlsson A. (1991) Vitamin C deficiency facilitates 5-S-cysteinyldopamine formation in guinea pig striatum. J. Neurochem. 56, 407-414.
    • (1991) J. Neurochem. , vol.56 , pp. 407-414
    • Fornstedt, B.1    Carlsson, A.2
  • 10
    • 0025014950 scopus 로고
    • An improved HPLC-electrochemical detection method for measuring brain levels of 5-S-cysteinyldopamine, 5-S-cysteinyl-3,4-dihydroxyphenylalanine, and 5-S-cysteinyl-3,4-dihydroxyphenylacetic acid
    • Fornstedt B., Bergh I., Rosengren E., and Carlsson A. (1990) An improved HPLC-electrochemical detection method for measuring brain levels of 5-S-cysteinyldopamine, 5-S-cysteinyl-3,4-dihydroxyphenylalanine, and 5-S-cysteinyl-3,4-dihydroxyphenylacetic acid. J. Neurochem. 54, 578-586.
    • (1990) J. Neurochem. , vol.54 , pp. 578-586
    • Fornstedt, B.1    Bergh, I.2    Rosengren, E.3    Carlsson, A.4
  • 12
    • 0027937548 scopus 로고
    • Oxidative stress: Free radical production in neural degeneration
    • Götz M. E., Künig G., Riederer P., and Youdim M. B. H. (1994) Oxidative stress: free radical production in neural degeneration. Pharmacol. Ther. 63, 37-122.
    • (1994) Pharmacol. Ther. , vol.63 , pp. 37-122
    • Götz, M.E.1    Künig, G.2    Riederer, P.3    Youdim, M.B.H.4
  • 13
    • 0031029150 scopus 로고    scopus 로고
    • A novel reaction mechanism for the formation of S-nitrosothiol in vivo
    • Gow A. J., Buerk D. G., and Ischiropoulos H. (1997) A novel reaction mechanism for the formation of S-nitrosothiol in vivo. J. Biol. Chem. 272, 2841-2845.
    • (1997) J. Biol. Chem. , vol.272 , pp. 2841-2845
    • Gow, A.J.1    Buerk, D.G.2    Ischiropoulos, H.3
  • 14
    • 0018095085 scopus 로고
    • Oxidative pathways for catecholamines in the genesis of neuromelanin and cytotoxic quinones
    • Graham D. G. (1978) Oxidative pathways for catecholamines in the genesis of neuromelanin and cytotoxic quinones. Mol. Pharmacol. 14, 633-643.
    • (1978) Mol. Pharmacol. , vol.14 , pp. 633-643
    • Graham, D.G.1
  • 15
    • 0032531735 scopus 로고    scopus 로고
    • Electrochemical analysis of protein nitrotyrosine and dityrosine in the Alzheimer's brain indicate region-specific accumulation
    • Hensley K., Maidt M. L., Yu Z., Sang H., Markesbery W. R., and Floyd R. A. (1998) Electrochemical analysis of protein nitrotyrosine and dityrosine in the Alzheimer's brain indicate region-specific accumulation. J. Neurosci. 18, 8126-8132.
    • (1998) J. Neurosci. , vol.18 , pp. 8126-8132
    • Hensley, K.1    Maidt, M.L.2    Yu, Z.3    Sang, H.4    Markesbery, W.R.5    Floyd, R.A.6
  • 16
    • 37049135943 scopus 로고
    • The chemistry of peroxonitrites. Part I. The kinetics of decomposition of peroxynitrous acid
    • Hughes M. N. and Nicklin H. G. (1968) The chemistry of peroxonitrites. Part I. The kinetics of decomposition of peroxynitrous acid. J. Chem. Soc. (A) 450-453.
    • (1968) J. Chem. Soc. (A) , pp. 450-453
    • Hughes, M.N.1    Nicklin, H.G.2
  • 17
    • 0002626655 scopus 로고
    • Phenylpropanoids
    • Dey P. M. and Harborne J. B., eds, Academic Press, London
    • Ibrahim R. and Barren D. (1989) Phenylpropanoids, in Methods in Plant Biochemistry (Dey P. M. and Harborne J. B., eds), pp. 75-111. Academic Press, London.
    • (1989) Methods in Plant Biochemistry , pp. 75-111
    • Ibrahim, R.1    Barren, D.2
  • 18
    • 0029751104 scopus 로고    scopus 로고
    • Oxidative stress and the pathogenesis of Parkinson's disease
    • Jenner P. and Olanow W. C. (1996) Oxidative stress and the pathogenesis of Parkinson's disease. Neurology 47, S161-S170.
    • (1996) Neurology , vol.47
    • Jenner, P.1    Olanow, W.C.2
  • 19
    • 0031687793 scopus 로고    scopus 로고
    • Understanding cell death in Parkinson's disease
    • Jenner P. and Olanow W. C. (1998) Understanding cell death in Parkinson's disease. Ann. Neurol. 44, S72-S84.
    • (1998) Ann. Neurol. , vol.44
    • Jenner, P.1    Olanow, W.C.2
  • 20
    • 0026635461 scopus 로고
    • Oxidative stress as a cause of nigral cell-death in Parkinson's disease and incidental Lewy body disease
    • Jenner P., Dexter D. T., Sian J., Schapira A. H. V., and Marsden C. D. (1992) Oxidative stress as a cause of nigral cell-death in Parkinson's disease and incidental Lewy body disease. Ann. Neurol. 32, S82-S87.
    • (1992) Ann. Neurol. , vol.32
    • Jenner, P.1    Dexter, D.T.2    Sian, J.3    Schapira, A.H.V.4    Marsden, C.D.5
  • 21
    • 0031416665 scopus 로고    scopus 로고
    • Spin-trapping of free radicals formed during the oxidation of glutathione by tetramethylammonium peroxynitrite
    • Karoui H., Hansert B., Sand P. J., Tordo P., Bohle D. S., and Kalyanraman B. (1997) Spin-trapping of free radicals formed during the oxidation of glutathione by tetramethylammonium peroxynitrite. Nitric Oxide: Biol. Med. 1, 346-358.
    • (1997) Nitric Oxide: Biol. Med. , vol.1 , pp. 346-358
    • Karoui, H.1    Hansert, B.2    Sand, P.J.3    Tordo, P.4    Bohle, D.S.5    Kalyanraman, B.6
  • 22
    • 0031952528 scopus 로고    scopus 로고
    • Novel endogenous 1,2,3,4-tetrahydroisoquinoline derivatives: Uptake by dopamine transporter and activity to induce parkinsonism
    • Kawai H., Makino Y., Hirobe M., and Ohta S. (1998) Novel endogenous 1,2,3,4-tetrahydroisoquinoline derivatives: uptake by dopamine transporter and activity to induce parkinsonism. J. Neurochem. 70, 745-751.
    • (1998) J. Neurochem. , vol.70 , pp. 745-751
    • Kawai, H.1    Makino, Y.2    Hirobe, M.3    Ohta, S.4
  • 23
    • 0032561404 scopus 로고    scopus 로고
    • Peroxynitrite oxidises catechols to o-quinones
    • Kerry N. and Rice-Evans C. (1998) Peroxynitrite oxidises catechols to o-quinones. FEBS Lett. 437, 167-171.
    • (1998) FEBS Lett. , vol.437 , pp. 167-171
    • Kerry, N.1    Rice-Evans, C.2
  • 24
    • 0028089211 scopus 로고
    • Striatal transporter for dopamine: Catechol structure-activity studies and susceptibility to chemical modification
    • Meiergerd S. M. and Schenk J. O. (1994) Striatal transporter for dopamine: catechol structure-activity studies and susceptibility to chemical modification. J. Neurochem. 62, 998-1008.
    • (1994) J. Neurochem. , vol.62 , pp. 998-1008
    • Meiergerd, S.M.1    Schenk, J.O.2
  • 25
    • 0028167292 scopus 로고
    • Chromatographic analyses of the effects of glutathione, cysteine and ascorbic acid on the monophenol and diphenol oxidase activity of tyrosinase
    • Nappi A. J. and Vass E. (1994) Chromatographic analyses of the effects of glutathione, cysteine and ascorbic acid on the monophenol and diphenol oxidase activity of tyrosinase. J. Liq. Chromatogr. 17, 793-815.
    • (1994) J. Liq. Chromatogr. , vol.17 , pp. 793-815
    • Nappi, A.J.1    Vass, E.2
  • 26
    • 0032411537 scopus 로고    scopus 로고
    • Inhibition of nitrous acid-dependent tyrosine nitration and DNA base deamination by flavonoids and other phenolic compounds
    • Oldreive C., Zhao K., Paganga G., Halliwell B., and Rice-Evans C. (1998) Inhibition of nitrous acid-dependent tyrosine nitration and DNA base deamination by flavonoids and other phenolic compounds. Chem. Res. Toxicol. 11, 1574-1579.
    • (1998) Chem. Res. Toxicol. , vol.11 , pp. 1574-1579
    • Oldreive, C.1    Zhao, K.2    Paganga, G.3    Halliwell, B.4    Rice-Evans, C.5
  • 27
    • 0028867889 scopus 로고
    • Iron- and peroxide-dependent conjugation of dopamine with cysteine: Oxidative routes to the novel brain metabolite 5-S-cysteinyldopamine
    • Palumbo A., d'Ischia M., Misuraca G., De Martino L., and Prota G. (1995) Iron- and peroxide-dependent conjugation of dopamine with cysteine: oxidative routes to the novel brain metabolite 5-S-cysteinyldopamine. Biochim. Biophys. Acta 1245, 255-261.
    • (1995) Biochim. Biophys. Acta , vol.1245 , pp. 255-261
    • Palumbo, A.1    D'Ischia, M.2    Misuraca, G.3    De Martino, L.4    Prota, G.5
  • 28
    • 0031555883 scopus 로고    scopus 로고
    • Inhibition of peroxynitrite-mediated tyrosine nitration by catechin polyphenols
    • Pannala A., Rice-Evans C., Halliwell B., and Singh S. (1997) Inhibition of peroxynitrite-mediated tyrosine nitration by catechin polyphenols. Biochem. Biophys. Res. Commun. 232, 164-168.
    • (1997) Biochem. Biophys. Res. Commun. , vol.232 , pp. 164-168
    • Pannala, A.1    Rice-Evans, C.2    Halliwell, B.3    Singh, S.4
  • 29
    • 0032032712 scopus 로고    scopus 로고
    • Inhibition of peroxynitrite dependent nitration by hydroxycinnamic acids: Nitration or electron donation?
    • Pannala A., Razzaq R., Halliwell B., Singh S., and Rice-Evans C. (1998) Inhibition of peroxynitrite dependent nitration by hydroxycinnamic acids: nitration or electron donation? Free Radic. Biol. Med. 24, 594-606.
    • (1998) Free Radic. Biol. Med. , vol.24 , pp. 594-606
    • Pannala, A.1    Razzaq, R.2    Halliwell, B.3    Singh, S.4    Rice-Evans, C.5
  • 30
    • 0025730414 scopus 로고
    • Peroxynitrite oxidation of sulfhydryls - The cytotoxic potential of superoxide and nitric oxide
    • Radi R., Beckman J. S., Bush K. M., and Freeman B. A. (1990) Peroxynitrite oxidation of sulfhydryls - the cytotoxic potential of superoxide and nitric oxide. J. Biol. Chem. 266, 4244-4250.
    • (1990) J. Biol. Chem. , vol.266 , pp. 4244-4250
    • Radi, R.1    Beckman, J.S.2    Bush, K.M.3    Freeman, B.A.4
  • 31
    • 0029888128 scopus 로고    scopus 로고
    • Structure-antioxidant activity relationships of flavonoids and phenolic acids
    • Rice-Evans C. A., Miller N. J., and Paganga G. (1996) Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic. Biol. Med. 20, 933-956.
    • (1996) Free Radic. Biol. Med. , vol.20 , pp. 933-956
    • Rice-Evans, C.A.1    Miller, N.J.2    Paganga, G.3
  • 34
    • 0014527402 scopus 로고
    • Zur Kenntnis der Farbreaktion von Adrenalin mit salpetriger Säure
    • Roth H. J. and Volkmann U. (1969) Zur Kenntnis der Farbreaktion von Adrenalin mit salpetriger Säure. Arch. Pharmacol. 302, 434-456.
    • (1969) Arch. Pharmacol. , vol.302 , pp. 434-456
    • Roth, H.J.1    Volkmann, U.2
  • 35
    • 0346386580 scopus 로고    scopus 로고
    • Widespread peroxynitrite-mediated damage in Alzheimer's disease
    • Smith M. A., Harris P. L. R., Sayre L. M., Beckman J. S., and Perry G. (1997) Widespread peroxynitrite-mediated damage in Alzheimer's disease. J. Neurosci. 17, 2653-2657.
    • (1997) J. Neurosci. , vol.17 , pp. 2653-2657
    • Smith, M.A.1    Harris, P.L.R.2    Sayre, L.M.3    Beckman, J.S.4    Perry, G.5
  • 36
    • 0031722906 scopus 로고    scopus 로고
    • Conjugates of catecholamines with cysteine and GSH in Parkinson's disease: Possible mechanisms of formation involving reactive oxygen species
    • Spencer J. P. E., Jenner P., Daniel S. E., Lees A. J., Marsden D. C., and Halliwell B. (1998) Conjugates of catecholamines with cysteine and GSH in Parkinson's disease: possible mechanisms of formation involving reactive oxygen species. J. Neurochem. 71, 2112-2122.
    • (1998) J. Neurochem. , vol.71 , pp. 2112-2122
    • Spencer, J.P.E.1    Jenner, P.2    Daniel, S.E.3    Lees, A.J.4    Marsden, D.C.5    Halliwell, B.6
  • 37
    • 0031558654 scopus 로고    scopus 로고
    • Neuronal DNA damage precedes tangle formation and is associated with up-regulation of nitrotyrosine in Alzheimer's brain
    • Su J. H., Deng G. M., and Cotman C. W. (1997) Neuronal DNA damage precedes tangle formation and is associated with up-regulation of nitrotyrosine in Alzheimer's brain. Brain Res. 774, 193-199.
    • (1997) Brain Res. , vol.774 , pp. 193-199
    • Su, J.H.1    Deng, G.M.2    Cotman, C.W.3
  • 38
    • 0016907344 scopus 로고
    • Potential oxidative pathways of brain catecholamines
    • Tse D. C. S., McCreery R. L., and Adams R. W. (1976) Potential oxidative pathways of brain catecholamines. J. Med. Chem. 19, 37-40.
    • (1976) J. Med. Chem. , vol.19 , pp. 37-40
    • Tse, D.C.S.1    McCreery, R.L.2    Adams, R.W.3
  • 39
    • 0016829830 scopus 로고
    • Synthetic amino acids and the nature of L-dopa transport at the blood-brain barrier
    • Wade L. A. and Katzman R. (1975) Synthetic amino acids and the nature of L-dopa transport at the blood-brain barrier. J Neurochem. 25, 837-843.
    • (1975) J Neurochem. , vol.25 , pp. 837-843
    • Wade, L.A.1    Katzman, R.2
  • 40
    • 0027732025 scopus 로고
    • Oxidation chemistry of dopamine: Possible insights into the age-dependent loss of dopaminergic nigrostriatal neurons
    • Zhang F. and Dryhurst G. (1993) Oxidation chemistry of dopamine: possible insights into the age-dependent loss of dopaminergic nigrostriatal neurons. Bioorg. Chem. 21, 392-410.
    • (1993) Bioorg. Chem. , vol.21 , pp. 392-410
    • Zhang, F.1    Dryhurst, G.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.