Adrenochrome, a stable oxidation product formed after oxidation of adrenaline, strongly stimulates oxygen uptake occurring during the autoxidation of adrenaline, other catecholamines and ascorbate. Oxygen consumed is converted to hydrogen peroxide suggesting the occurrence of a redox cycling process. The reduction of adrenochrome operated by adrenaline is accelerated by the exclusion of oxygen indicating that the oxidation of adrenaline occurs directly and superoxide anion does not necessarily mediate it. Oxygen consumption, observed in the catecholamine/adrenochrome and ascorbate/adrenochrome systems, is due to the autoxidation of leucoadrenochrome that, at variance with adrenaline, easily autoxidizes also at physiological pH. Therefore, in these systems, leucoadrenochrome appears to be the major determinant of the production of superoxide anion.
This is a preview of subscription content, log in to check access.
Buy single article
Instant access to the full article PDF.
Price includes VAT for USA
Subscribe to journal
Immediate online access to all issues from 2019. Subscription will auto renew annually.
This is the net price. Taxes to be calculated in checkout.
diethylenetriamine pentaacetic acid
Ball, E.G. and Chen, T. (1933) Studies on oxidation-reduction. XX. Epinephrine and related compounds.J. Biol. Chem. 102, 691–719.
Bindoli, A., Rigobello, M.P. and Galzigna, L. (1988) Production of reduced forms of oxygen by adrenochrome in the presence of ascorbate, microsomes and submitochondrial particles. In: Rice Evans, C. and Dormandy, T. (Eds.),Free Radicals: Chemistry, Pathology and Medicine (Richelieu Press, London), pp. 293–300.
Bindoli, A., Rigobello, M.P. and Galzigna, L. (1989) Toxicity of aminochromes.Toxicology Lett. 48, 3–20.
Bindoli, A., Deeble, D.J., Rigobello, M.P. and Galzigna, L. (1990a) Direct and respiratory chain-mediated redox cycling of adrenochrome.Biochim. Biophys. Acta 1016, 349–356.
Bindoli, A., Rigobello, M.P. and Galzigna, L. (1990b) Reduction of adrenochrome by rat liver and brain DT-diaphorase.Free Rad. Res. Coram. 8, 295–298.
Bindoli, A., Rigobello, M.P. and Deeble, D.J. (1992) Biochemical and toxicological properties of the oxidation products of catecholamines.Free Radical Biol. Med. 13, 391–405.
Bors, W., Saran, M., Michael, C, Lengfelder, E., Fuchs, C. and Spottl, R. (1975) Pulse-radiolytic investigation of catechols and catecholamines. I. Adrenaline and adrenochrome.Int. ]. Radiat. Biol. 28, 353–371.
Bors, W., Michel, C., Saran, M. and Lengfelder, E. (1978a). The involvement of oxygen radicals during the autoxidation of adrenalin.Biochim. Biophys. Acta 540, 162–172.
Bors, W., Saran, M., Lengfelder, E., Michel, C, Fuchs, C. and Frenzel, C. (1978b) Detection of oxygen radicals in biological reactions.Photochem. Photobiol. 28, 629–638.
Cazzaro, E, Rigobello, M.P. and Bindoli, A. (1996) Personal computer control of electrochemical detectors utilized for mitochondrial studies.Comput. Methods Progr. Biomed. 51, 141–151.
Cook, J.A., Wink, D.A., Blount, V., Krishna, M.C. and Hanbauer, I. (1996) Role of antioxidants in the nitric oxide-elicited inhibition of dopamine uptake in cultured mesencephalic neurons. Insight into potential mechanisms of nitric oxide-mediated neurotoxicity.Neurochem. Intern. 28, 609–617.
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 1, 234–243.
Ernster, L. (1967) DT-diaphorase.Methods Enzymol. 10, 309–317.
Ernster, L. (1987) DT-diaphorase: a historical review.Chemica Scripta 27A, 1–13.
Estabrook, R.W. (1967) Mitochondrial respiratory control and the polarographic measurement of ADP: O ratios.Methods Enzymol. 10, 41–47.
Falk, J.E. (1949) The formation of hydrogen carriers by haematin-catalyzed peroxidations. 2. Some reactions of adrenaline and adrenochrome.Biochem. J. 44, 369–373.
Fornstedt, B., Rosengren, E. and Carlsson, A. (1986) Occurrence and distribution of 5-S-cysteinyl derivatives of dopamine, dopa and dopac in the brains of eight mammalian species.Neuropharmacology 25, 451–454.
Green, D.E. and Richter, D. (1937) Adrenaline and adrenochrome.Biochem. J. 31, 596–616.
Hastings, T.G. (1995) Enzymatic oxidation of dopamine: the role of prostaglandin H synthase.J. Neurochem. 64, 919–924.
Hawley, M.D., Tatawawadi, S.V., Piekarsky, S. and Adams, R.N. (1967) Electrochemical studies of the oxidation pathways of catecholamines.J. Am. Chem. Soc. 89, 447–450.
Heacock, R.A. (1959) The chemistry of adrenochrome and related compounds.Chem. Rev. 59, 181–237.
Heacock, R.A. and Powell, W.S. (1973) Adrenochrome and related compounds. In: Ellis, G.P. and West, G.B. (Eds.),Progress in Medicinal Chemistry. Vol. 9 (North Holland, Amsterdam) pp. 275–339.
Hoffer, A., Osmond, H. and Smythies, J.R. (1954) Schizophrenia. A new approach. Part II.J. Ment. Sci. 100, 29–45.
Jewett, S.L., Eddy, L.J. and Hochstein, P. (1989) Is the autoxidation of catecholamines involved in ischemia-reperfusion injury?Free Radical Biol. Med. 6, 185–188.
Kalyanaraman, B., Felix, C.C. and Sealy, R.C. (1984) Electron-spin resonance-spin stabilization of semiquinones produced during oxidation of epinephrine and its analogues.J. Biol. Chem. 259, 354–358.
Kalyanaraman, B., Korytowski, W., Pilas, B., Sarna, T, Land, E.J. and Truscott, T.G. (1988) Reaction between ortho-semiquinones and oxygen: pulse radiolysis, electron spin resonance and oxygen uptake studies.Arch. Biochem. Biophys. 266, 277–284.
Lowry, O.H., Rosebrough, N.J., Farr, A.L. and Randall, R.J. (1951) Protein measurement with the Folia phenol reagent.J. Biol. Chem. 193, 265–293.
Mattammal, M.B., Strong, R., Lakshmi, V.M., Chung, H.D. and Stephenson, A.H. (1995) Prostaglandin H synthetase-mediated metabolism of dopamine: implication for Parkinson’s disease.J. Neurochem. 64, 1645–1654.
Matthews, S.B., Henderson, A.H. and Campbell, A.K. (1985a) The adrenochrome pathway: the major route for adrenalin catabolism by polymorphonuclear leucocytes.J. Mol. Cell. Cardiol. 17, 339–348.
Matthews, S.B., Hallet, M.B., Henderson, A.H. and Campbell, A.K. (1985b) The adrenochrome pathway: a potential catabolic route for adrenaline metabolism in inflammatory disease.Adv. Myocardiol. 6, 367–381.
Misra, H.P. and Fridovich, I. (1972) The role of superoxide anion in the autoxidation of epinephrine and a simple assay for superoxide dismutase.J. Biol. Chem. 247, 3170–3175.
Mukherjee, T. (1987) One-electron reduction of juglone (5-hydroxy-l,4-naphthoquinone): a pulse radiolysis study.Radiat. Phys. Chem. 29, 455–462.
Pileblad, E., Slivka, A., Bratvold, D. and Cohen, G. (1988) Studies on the autoxidation of dopamine: interaction with ascorbate.Arch. Biochem. Biophys. 263, 447–452.
Rosengren, E., Linder-Eliasson, E. and Carlsson, A. (1985) Detection of 5-S-cysteinyl-dopamine in human brain.J. Neurol. Transm. 63, 247–253.
Smythies, J. (1996) On the function of neuromelanin.Proc. R. Soc. London B 263, 487–489.
Smythies, J. and Galzigna, L. (1998) The oxidative metabolism of catecholamines in the brain: a review.Biochim. Biophys. Acta 1380, 159–162.
Vulpian, E.F.A. (1856) Notes sur quelques reactions propres a la substance des capsules surrenales.C.R. Acad. Sci. 43, 663–665.
Wiesner, K. (1942) Polarographische Untersuchung des Adrenochroms.Biochem. Z. 313, 48–61.
Yoshie, Y. and Ohshima, H. (1997) Synergistic induction of DNA strand breakage caused by nitric oxide together with catecholamines: implication for neurodegenerative disease.Chem. Res. Toxicol. 10, 1015–1022.
About this article
Cite this article
Bindoli, A., Scutari, G. & Rigobello, M.P. The role of adrenochrome in stimulating the oxidation of catecholamines. neurotox res 1, 71–80 (1999). https://doi.org/10.1007/BF03033271
- Catecholamine oxidation
- Redox cycling