Endogenous and Dietary Indoles: A Class of Antioxidants and Radical Scavengers in the ABTS Assay

References

• Halliwell, B. (1996) "Antioxidants in human health and disease", Annu. Rev. Nutr. 16, 33–50.
   PubMed Web of Science ®Google Scholar
• Halliwell, B. and Gutteridge, J.M.C. (1990) "Role of free radicals and catalytic metal ions in human disease: an overview", Meth. Enzymol. 186, 1–85.
   PubMed Web of Science ®Google Scholar
• Fang, Y-Z., Yang, S. and Wu, G. (2002) "Free radicals, antioxidants, and nutrition", Nutrition 18, 872–879.
   Google Scholar
• Aruoma, 0.1. (1994) "Nutrition and health aspects of free radicals and antioxidants", Food Chem. Toxicol. 32, 671–683.
   PubMed Web of Science ®Google Scholar
• Halliwell, B. (1999) "Food-derived antioxidants. Evaluating their importance in food and in vivo", Food Sci. Agric. Chem. 1, 67–109.
   Google Scholar
• Halliwell, B. and Gutteridge, J.M.C. (1999) Free Radical in Biology and Medicine, 3rd Edn. (Oxford University Press).
   Google Scholar
• Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M. and Rice-Evans, C. (1999) "Antioxidant activity applying an improved ABTS radical cation decolorization assay", Free Radic. Biol. Med. 26, 1231–1237.
   PubMed Web of Science ®Google Scholar
• Bradlow, H.L., Sepkovic, D.W., Telang, N.T. and Osborne, M.P. (1999) "Multifunctional aspects of the action of indole-3-carbinol as an antitumor agent", Ann. NY Acad. Sci. 889, 204–213.
   PubMedGoogle Scholar
• Shertzer, HG., Berger, M.L. and Tabor, M.W. (1988) "Intervention in free radical mediated hepatotoxicity and lipid peroxidation by indole-3-carbinol", Biochem. Pharmacol. 37, 333–338.
   PubMed Web of Science ®Google Scholar
• Arnao, MB., Sanchez-Bravo, J. and Acosta, M. (1996) "Indole-3-carbinol as a scavenger of free radicals", Biochem. Mol. Biol. Int. 39, 1125–1134.
   Google Scholar
• Bradfield, CA. and Bjeldanes, L.F. (1991) "Modification of carcinogenic metabolism by indolytic autolysis products of Brassica oleraceae", Adv. Exp. Med. Biol. 289, 153–163.
   PubMedGoogle Scholar
• Reiter, R.J., Tang, T., Garcia, J.J. and Mutioz-Hoyos, A. (1997) "Pharmacological actions of melatonin in oxygen radical pathophysiology", Life Sci. 60, 2255–2271.
   PubMed Web of Science ®Google Scholar
• Reiter, R.J., Cabrera, J., Sainz, R.M., Mayo, J.C., Manchester, L.C. and Tan, D.-X. (1999) "Melatonin as a pharmacological agent against neuronal loss in experimental models of Huntington's disease, Alzheimer's disease and Parkinson-ism", Ann. NY Acad. Sci. 890, 471–485.
   PubMedGoogle Scholar
• Broadbent, T.A. and Broadbent, H.S. (1998) "The chemistry and pharmacology of indole-3-carbinol (indole-3-methanol) and 3-methoxymethylindole. Part I", Curr. Med. Chem. 5, 337–352.
   PubMed Web of Science ®Google Scholar
• Stolc, S., Vlkolinsky, R. and Pavlasek (1997) "Neuroprotection by the pyridoindole stobadine: a minireview", Brain Res. Bull. 42, 335–340.
   PubMedGoogle Scholar
• Vincenzi, EE and Hinds, T.R. (1999) "Stobadine: bellwether of a broader view of drug actions", Life Sci. 65, 1857–1864.
   PubMedGoogle Scholar
• Herraiz, T. (1996) "Occurrence of tetrahydro-13-carboline-3-carboxylic acids in commercial foodstuffs", J. Agric. Food Chem. 44, 3057–3065.
   Web of Science ®Google Scholar
• Herraiz, T. (1998) "Occurrence of 1,2,3,4-tetrahydro-13-carbo-line-3-carboxylic acid and 1-methyl-1,2,3,4-tetrahydro-13-carboline-3-carboxylic acid in fruit juices, purees and jams", J. Agric. Food Chem. 46, 3484–3490.
   Google Scholar
• Herraiz, T. (2001) "Advances in the identification and analysis of the bioactive 13-carboline alkaloids in food and biological samples", Current Topics in Analytical Chemistry (Ed. Research Trends, Trivandrum) 2, pp 171–177.
   Google Scholar
• Herraiz, T. (2000) "Analysis of the bioactive alkaloids tetrahydro-13-carboline and 13-carboline in food", J. Chromatogr. A 881, 483–499.
   PubMed Web of Science ®Google Scholar
• Airaksinen, M.M. and Kari, I. (1981) "13-carbolines, psycho-active compounds in the mammalian body", Med. Biol. 59, 21–34.
   PubMedGoogle Scholar
• Rommelspacher, H., May, T. and Susilo, R. (1991) "13-Carbolines and Tetrahydroisoquinolines: detection and function in mammals", Planta Med. 57, S85—S92.
   Google Scholar
• Glennon, R.A., Dukat, D.M., Grella, B., Hong, S., Costantino, L., Teitler, M., Smith, C., Egan, C., Davis, K. and Mattson, M.V. (2000) "Binding of 13-carbolines and related agents at serotonin (5HT(2) and 5-HT(1A)), dopamine (D(2) and benzodiazepine receptors", Drug Alcohol Depend. 60, 121–132.
   PubMed Web of Science ®Google Scholar
• Yu, A.-M., Idle, J.R., Herraiz, T., Kiipfer, A. and Gonzalez, F.J. (2003) "Screening for endogenous substrates reveals that CYP2D6 is a methoxyindolemethylamine 0-demethylase", Pharmacogenetics 13, 307–319.
   PubMedGoogle Scholar
• Herraiz, T. and Galisteo, J. (2002) "Tetrahydro-13-carboline alkaloids that occur in foods and biological systems act as radical scavengers and antioxidants in the ABTS assay", Free Radic. Res. 36, 923–928.
   PubMed Web of Science ®Google Scholar
• Long, L.H. and Halliwell, B. (2001) "Antioxidant and prooxidant abilities of foods and beverages", Meth. Enzymol. 335, 181–190.
   PubMed Web of Science ®Google Scholar
• Long, L.H., Kwee, D.C.T. and Halliwell, B. (2000) "The antioxidant activities of seasonings used in Asian cooking. Powerful antioxidant activity of dark soy sauce revealed using the ABTS assay", Free Radic. Res. 32, 181–186.
   PubMed Web of Science ®Google Scholar
• Miller, N.J., Rice-Evans, C. and Davies, M.J. (1993) "A new method for measuring antioxidant activity", Biochem. Soc. Trans. 21, 95S.
   Google Scholar
• Tyrakowska, B., Soffer, A.E.M.F., Szymusiak, H., Boeren, S., Boersma, M.G., Lemanska, K., Vervoort, J. and Rietjens, I.M.C.M. (1999) "TEAC antioxidant activity of 4-hydroxy-benzoates", Free Radic. Biol. Med. 27, 1227–1436.
   Google Scholar
• Jovanovic, S.V., Steenken, S. and Simic, MG. (1991) "Kinetics and energetics of one-electron-transfer reactions involving tryptophan neutral and cation radicals", J. Phys. Chem. 95, 684–687.
   Google Scholar
• Poeggeler, B., Saarela, S., Reiter, R.J., Tan, D-X., Chen, L-D., Manchester, L.C. and Barlow-Walden, L.R. (1994) "Melatonin- A highly potent endogenous radical scavenger and electron donor: New aspects of the oxidation chemistry of this indole accessed in vitro", Ann. NY Acad. Sci. 738, 419–420.
   PubMedGoogle Scholar
• Turianski, A.G., Rosenstein, R.E. and Estrin, D.A. (1998) "Reactions of melatonin and related indoles with free radicals: a computational study", J. Med. Chem. 41,3684–3689.
   PubMedGoogle Scholar
• Fang, X., Jin, F., Jin, H. and von Sonntag, C. (1998) "Reaction of the superoxide radical with the N-centered radical derived from N-acetyltryptophan methyl ester", J. Chem. Soc., Perkin Trans. 2, 259–263.
   Google Scholar
• Lissi, E.A., Faure, M., Montoya, N. and Videla, L.A. (1991) "Reactivity of indole derivatives towards oxygenated radicals", Free Radic. Res. Commun. 15, 211–222.
   PubMed Web of Science ®Google Scholar
• Liu, J. and Mori, A. (1993) "Monoamine metabolism provides an antioxidant defense in the brain against oxidant- and free radical-induced damage", Arch. Biochem. Biophys. 302, 118–127.
   PubMed Web of Science ®Google Scholar
• Poeggeler, B., Pappolla, MA., Hardeland, R., Rassoulpour, A., Hodgkins, P.S., Ghidetti, P. and Schwarcz, R. (1999) "Indole-3-propionate: a potent hydroxyl radical scavenger in rat brain", Brain Res. 815, 382–388.
   PubMed Web of Science ®Google Scholar
• Karbownik, M., Reiter, R.J., Garcia, J.J., Cabrera, J., Burkhardt, S., Osuna, C. and Lewinski, A. (2001) "Indole-3-propionic acid, a melatonin-related molecule protect hepatic microsomal membranes from iron induced oxidative damage: relevance to cancer reduction", J. Cell Biochem. 81, 507–513.
   PubMed Web of Science ®Google Scholar
• Mayo, J.C., Tan, DX., Sainz, R.M., Natarajan, M., Lopez-Burin°, S. and Reiter, R.J. (2003) "Protection against oxidative protein damage induced by metal-catalyzed reaction or alkylperoxyl radicals: comparative effects of melatonin and other antioxidants", Biochem. Biophys. Acta 1620, 139–150.
   PubMedGoogle Scholar
• Irwin, J.A., Ostdal, H. and Davies, M.J. (1999) "Myoglobin-induced oxidative damage: evidence for radical transfer from oxidized myoglobin to other proteins and antioxidants", Arch. Biochem. Biophys. 362, 94–104.
   PubMed Web of Science ®Google Scholar
• Horakova, L., Gief3auf, A., Raber, G. and Esterbauer, H. (1996) "Effect of Stobadine on Cu+ ± -mediated oxidation of low-density lipoprotein", Biochem. Pharmacol. 51, 1277–1282.
   PubMedGoogle Scholar
• Hoey, B.M. and Butler, J. (1984) "The repair of oxidized amino acids by antioxidants", Biochem. Biophys. Acta 791, 212–218.
   PubMed Web of Science ®Google Scholar
• Matuszak, Z., Reszka, K.J. and Chignell, C.F. (1997) "Reaction of melatonin and related indoles with hydroxyl radicals: EPR and Spin trapping investigations", Free Radic. Biol. Med. 23, 367–372.
   PubMed Web of Science ®Google Scholar
• Menendez-Pelaez, A., Poeggeler, B., Reiter, R.J., Barlow-Walden, L.R., Pablos, M.I. and Tan, D.-X. (1993) "Nuclear localization of melatonin in different mammalian tisssues: immunocytochemical and radioimmunoassay evi-dence", J. Cell. Biochem. 53, 372–382.
   Google Scholar
• Breum, L., Rasmussen, M.H., Hilsted, J. and Fernstrom, J.D. (2003) "Twenty-four-hour plasma tryptophan concentrations and ratios are below normal in obese subjects and are not normalized by substantial weight reduction", Am. J. Clin. Nutr. 77, 1112–1118.
   PubMed Web of Science ®Google Scholar
• Scaltbert, A. and Williamson, G. (2000) "Dietary intake and bioavailability of polyphenols", J. Nutr. 130, 2073S–2085S.
   Google Scholar
• Dryhurst, G. (1990) "Applications of electrochemistry in studies of the oxidation chemistry of central nervous system indoles", Chem. Rev. 90, 795–811.
   Google Scholar
• Folkes, L.K., Candeias, L.P. and Wardman, P. (1998) "Toward targeted "oxidation therapy" of cancer: pero)d-dase-catalyzed cytotoxicity of indole-3-acetic acid", Int. J. Radiat. Oncol. Biol. Phys. 42, 917–920.
   PubMed Web of Science ®Google Scholar
• Collins, MA. and Neafsey, E.J. (1985) "13-carboline analogs of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP): endogenous factors underlying idiophathic parkinsonism?", Neurosci. Lett. 55, 179–183.
   PubMed Web of Science ®Google Scholar