FREE SHIPPING over $40
OVER 9000 FIVE-STAR REVIEWS
5% OFF ALL SUBSCRIPTIONS
100% HAPPINESS GUARANTEE
Analyze Diet
0
Home / Equine Research Bank / Neuropharmacology / Occurrence and distribution of 5-S-cysteinyl derivatives of ...
Neuropharmacology1986; 25(4); 451-454; doi: 10.1016/0028-3908(86)90242-x

Occurrence and distribution of 5-S-cysteinyl derivatives of dopamine, dopa and dopac in the brains of eight mammalian species.

Abstract: The 5-S-cysteinyl derivatives of dopamine, dopa (3,4-dihydroxyphenylalanine) and dopac (3,4-dihydroxyphenylacetic acid) were synthesized and used as reference compounds in high performance liquid chromatography analyses of extracts from various brain regions of eight mammalian species. All three metabolites were detected in the brains of all the species studied. The regional distribution of the metabolites was similar to that of dopamine; the metabolite concentrations ranged from less than 0.1 percent to more than 1 percent of the dopamine level, the highest ratios generally being found in substantia nigra. It is suggested that the 5-S-cysteinyl catechol metabolites have been formed after autoxidation of catechols to quinones and subsequent coupling to glutathione. The adduct thus formed is finally split by peptidases to yield the 5-S-cysteinyl derivatives.
Get Full Text
Publication Date: 1986-04-01 PubMed ID: 3086766DOI: 10.1016/0028-3908(86)90242-xGoogle Scholar: Lookup
The Equine Research Bank provides access to a large database of publicly available scientific literature. Inclusion in the Research Bank does not imply endorsement of study methods or findings by Mad Barn.
LinkedInCopy
  • Comparative Study
  • Journal Article
  • Research Support
  • Non-U.S. Gov't

Summary

This research summary has been generated with artificial intelligence and may contain errors and omissions. Refer to the original study to confirm details provided. Submit correction.

This research paper studies the occurrence and distribution of certain types of dopamine, dopa and dopac derivatives in the brains of different mammals. The researchers synthesized these compounds and used them as references to examine their presence and location in the animals’ brains using high-performance liquid chromatography.

Methodology

  • The study began by synthesizing 5-S-cysteinyl derivatives of dopamine, dopa and dopac. These are chemical compounds linked to brain activity and neurotransmission.
  • These synthesized compounds served as reference points for their subsequent analysis.
  • High-performance liquid chromatography, a method used to separate and identify substances in a solution, was used to analyze extracts from various regions of the brains of eight different mammalian species.

Findings

  • The researchers were able to detect all three metabolites in the brains of every species studied, indicating a widespread occurrence of these compounds across mammalian species.
  • A patterning was observed in the distribution of these metabolites. Their regional distribution within the brain was found to be similar to that of dopamine, which is a neurotransmitter that helps regulate movement and emotional responses.
  • The concentration of these metabolites varied from being less than 0.1% to over 1% of the dopamine level, with the highest ratios usually observed in the substantia nigra, a region of the midbrain.

Conclusions and Future Research

  • The study suggests that these 5-S-cysteinyl catechol metabolites form after the autoxidation of catechols to quinones, which then couple onto glutathione.
  • The adduct formed through this process ultimately splits due to the action of peptidases, leading to the formation of the 5-S-cysteinyl derivatives.
  • This research provides insight into the chemical processes in the mammalian brain and could contribute to a better understanding of neurotransmission and neurological health.

Cite This Article

APA
Fornstedt B, Rosengren E, 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(4), 451-454. https://doi.org/10.1016/0028-3908(86)90242-x

Publication

Neuropharmacology
ISSN: 0028-3908
NlmUniqueID: 0236217
Country: England
Language: English
Volume: 25
Issue: 4
Pages: 451-454

Researcher Affiliations

Fornstedt, B
    Rosengren, E
      Carlsson, A

        MeSH Terms

        • Animals
        • Brain Chemistry
        • Callitrichinae
        • Cats
        • Cysteinyldopa / analogs & derivatives
        • Cysteinyldopa / analysis
        • Dihydroxyphenylalanine / analogs & derivatives
        • Dogs
        • Horses
        • Humans
        • Macaca mulatta
        • Rats
        • Sheep
        • Species Specificity

        Citations

        This article has been cited 32 times.
        1. Jakaria M, Cannon JR. Neuromelanin-induced cellular stress and neurotoxicity in the pathogenesis of Parkinson's disease. Apoptosis 2025 Dec;30(11-12):2481-2494.
          doi: 10.1007/s10495-025-02156-3pubmed: 40775594google scholar: lookup
        2. Fornstedt Wallin B. Oxidation of dopamine and related catechols in dopaminergic brain regions in Parkinson's disease and during ageing in non-Parkinsonian subjects. J Neural Transm (Vienna) 2024 Mar;131(3):213-228.
          doi: 10.1007/s00702-023-02718-2pubmed: 38238531google scholar: lookup
        3. García-Carmona JA, Amores-Iniesta J, Soler-Usero J, Cerdán-Sánchez M, Navarro-Zaragoza J, López-López M, Soria-Torrecillas JJ, Ballesteros-Arenas A, Pérez-Vicente JA, Almela P. Upregulation of Heat-Shock Protein (hsp)-27 in a Patient with Heterozygous SPG11 c.1951C>T and SYNJ1 c.2614G>T Mutations Causing Clinical Spastic Paraplegia. Genes (Basel) 2023 Jun 23;14(7).
          doi: 10.3390/genes14071320pubmed: 37510225google scholar: lookup
        4. Nagatsu T, Nakashima A, Watanabe H, Ito S, Wakamatsu K, Zucca FA, Zecca L, Youdim M, Wulf M, Riederer P, Dijkstra JM. The role of tyrosine hydroxylase as a key player in neuromelanin synthesis and the association of neuromelanin with Parkinson's disease. J Neural Transm (Vienna) 2023 May;130(5):611-625.
          doi: 10.1007/s00702-023-02617-6pubmed: 36939908google scholar: lookup
        5. Wulf M, Barkovits K, Schork K, Eisenacher M, Riederer P, Gerlach M, Eggers B, Marcus K. Neuromelanin granules of the substantia nigra: proteomic profile provides links to tyrosine hydroxylase, stress granules and lysosomes. J Neural Transm (Vienna) 2022 Oct;129(10):1257-1270.
          doi: 10.1007/s00702-022-02530-4pubmed: 35852604google scholar: lookup
        6. Raju D, Mendoza A, Wonnenberg P, Mohanaraj S, Sarbanes M, Truong C, Zestos AG. Polymer Modified Carbon Fiber-Microelectrodes and Waveform Modifications Enhance Neurotransmitter Metabolite Detection. Anal Methods 2019 Mar 28;11(12):1620-1630.
          doi: 10.1039/c8ay02737dpubmed: 34079589google scholar: lookup
        7. Young KZ, Cartee NMP, Ivanova MI, Wang MM. Thiol-mediated and catecholamine-enhanced multimerization of a cerebrovascular disease enriched fragment of NOTCH3. Exp Neurol 2020 Jun;328:113261.
          doi: 10.1016/j.expneurol.2020.113261pubmed: 32119934google scholar: lookup
        8. Goldstein DS, Kopin IJ. Linking Stress, Catecholamine Autotoxicity, and Allostatic Load with Neurodegenerative Diseases: A Focused Review in Memory of Richard Kvetnansky. Cell Mol Neurobiol 2018 Jan;38(1):13-24.
          doi: 10.1007/s10571-017-0497-xpubmed: 28488009google scholar: lookup
        9. Goldstein DS, Holmes C, Sullivan P, Jinsmaa Y, Kopin IJ, Sharabi Y. Elevated cerebrospinal fluid ratios of cysteinyl-dopamine/3,4-dihydroxyphenylacetic acid in parkinsonian synucleinopathies. Parkinsonism Relat Disord 2016 Oct;31:79-86.
          doi: 10.1016/j.parkreldis.2016.07.009pubmed: 27474472google scholar: lookup
        10. Cruz-Monteagudo M, Borges F, Paz-Y-Miño C, Cordeiro MN, Rebelo I, Perez-Castillo Y, Helguera AM, Sánchez-Rodríguez A, Tejera E. Efficient and biologically relevant consensus strategy for Parkinson's disease gene prioritization. BMC Med Genomics 2016 Mar 9;9:12.
          doi: 10.1186/s12920-016-0173-xpubmed: 26961748google scholar: lookup
        11. Goldstein DS, Jinsmaa Y, Sullivan P, Holmes C, Kopin IJ, Sharabi Y. Comparison of Monoamine Oxidase Inhibitors in Decreasing Production of the Autotoxic Dopamine Metabolite 3,4-Dihydroxyphenylacetaldehyde in PC12 Cells. J Pharmacol Exp Ther 2016 Feb;356(2):483-92.
          doi: 10.1124/jpet.115.230201pubmed: 26574516google scholar: lookup
        12. Xu S, Chan P. Interaction between Neuromelanin and Alpha-Synuclein in Parkinson's Disease. Biomolecules 2015 Jun 5;5(2):1122-42.
          doi: 10.3390/biom5021122pubmed: 26057626google scholar: lookup
        13. Wang YH, Xuan ZH, Tian S, Du GH. Echinacoside Protects against 6-Hydroxydopamine-Induced Mitochondrial Dysfunction and Inflammatory Responses in PC12 Cells via Reducing ROS Production. Evid Based Complement Alternat Med 2015;2015:189239.
          doi: 10.1155/2015/189239pubmed: 25788961google scholar: lookup
        14. Zucca FA, Basso E, Cupaioli FA, Ferrari E, Sulzer D, Casella L, Zecca L. Neuromelanin of the human substantia nigra: an update. Neurotox Res 2014 Jan;25(1):13-23.
          doi: 10.1007/s12640-013-9435-ypubmed: 24155156google scholar: lookup
        15. Koo U, Nam KW, Ham A, Lyu D, Kim B, Lee SJ, Kim KH, Oh KB, Mar W, Shin J. Neuroprotective effects of 3α-acetoxyeudesma-1,4(15),11(13)-trien-12,6α-olide against dopamine-induced apoptosis in the human neuroblastoma SH-SY5Y cell line. Neurochem Res 2011 Nov;36(11):1991-2001.
          doi: 10.1007/s11064-011-0523-1pubmed: 21688047google scholar: lookup
        16. González-Hernández T, Cruz-Muros I, Afonso-Oramas D, Salas-Hernandez J, Castro-Hernandez J. Vulnerability of mesostriatal dopaminergic neurons in Parkinson's disease. Front Neuroanat 2010;4:140.
          doi: 10.3389/fnana.2010.00140pubmed: 21079748google scholar: lookup
        17. Tiong CX, Lu M, Bian JS. Protective effect of hydrogen sulphide against 6-OHDA-induced cell injury in SH-SY5Y cells involves PKC/PI3K/Akt pathway. Br J Pharmacol 2010 Sep;161(2):467-80.
          doi: 10.1111/j.1476-5381.2010.00887.xpubmed: 20735429google scholar: lookup
        18. Guillot TS, Miller GW. Protective actions of the vesicular monoamine transporter 2 (VMAT2) in monoaminergic neurons. Mol Neurobiol 2009 Apr;39(2):149-70.
          doi: 10.1007/s12035-009-8059-ypubmed: 19259829google scholar: lookup
        19. Miyazaki I, Asanuma M. Approaches to prevent dopamine quinone-induced neurotoxicity. Neurochem Res 2009 Apr;34(4):698-706.
          doi: 10.1007/s11064-008-9843-1pubmed: 18770028google scholar: lookup
        20. Yuan WJ, Yasuhara T, Shingo T, Muraoka K, Agari T, Kameda M, Uozumi T, Tajiri N, Morimoto T, Jing M, Baba T, Wang F, Leung H, Matsui T, Miyoshi Y, Date I. Neuroprotective effects of edaravone-administration on 6-OHDA-treated dopaminergic neurons. BMC Neurosci 2008 Aug 1;9:75.
          doi: 10.1186/1471-2202-9-75pubmed: 18671880google scholar: lookup
        21. Ippolito JE. Current concepts in neuroendocrine cancer metabolism. Pituitary 2006;9(3):193-202.
          doi: 10.1007/s11102-006-0264-3pubmed: 17001465google scholar: lookup
        22. Ogawa N, Asanuma M, Miyazaki I, Diaz-Corrales FJ, Miyoshi K. L-DOPA treatment from the viewpoint of neuroprotection. Possible mechanism of specific and progressive dopaminergic neuronal death in Parkinson's disease. J Neurol 2005 Oct;252 Suppl 4:IV23-IV31.
          doi: 10.1007/s00415-005-4006-7pubmed: 16222434google scholar: lookup
        23. Asanuma M, Miyazaki I, Ogawa N. Dopamine- or L-DOPA-induced neurotoxicity: the role of dopamine quinone formation and tyrosinase in a model of Parkinson's disease. Neurotox Res 2003;5(3):165-76.
          doi: 10.1007/BF03033137pubmed: 12835121google scholar: lookup
        24. Bindoli A, Scutari G, Rigobello MP. The role of adrenochrome in stimulating the oxidation of catecholamines. Neurotox Res 1999 Dec;1(2):71-80.
          doi: 10.1007/BF03033271pubmed: 12835103google scholar: lookup
        25. Montine KS, Sidell KR, Zhang J, Montine TJ. Dopamine thioethers: formation in brain and neurotoxicity. Neurotox Res 2002 Nov-Dec;4(7-8):663-669.
          doi: 10.1080/1029842021000045435pubmed: 12709304google scholar: lookup
        26. Zecca L, Tampellini D, Gerlach M, Riederer P, Fariello RG, Sulzer D. Substantia nigra neuromelanin: structure, synthesis, and molecular behaviour. Mol Pathol 2001 Dec;54(6):414-8.
          pubmed: 11724917
        27. Zhang J, Perry G, Smith MA, Robertson D, Olson SJ, Graham DG, Montine TJ. Parkinson's disease is associated with oxidative damage to cytoplasmic DNA and RNA in substantia nigra neurons. Am J Pathol 1999 May;154(5):1423-9.
          doi: 10.1016/S0002-9440(10)65396-5pubmed: 10329595google scholar: lookup
        28. Wang W, Noël S, Desmadril M, Guéguen J, Michon T. Kinetic evidence for the formation of a Michaelis-Menten-like complex between horseradish peroxidase compound II and di-(N-acetyl-L-tyrosine). Biochem J 1999 May 15;340 ( Pt 1)(Pt 1):329-36.
          pubmed: 10229689
        29. LaVoie MJ, Hastings TG. Dopamine quinone formation and protein modification associated with the striatal neurotoxicity of methamphetamine: evidence against a role for extracellular dopamine. J Neurosci 1999 Feb 15;19(4):1484-91.
          doi: 10.1523/JNEUROSCI.19-04-01484.1999pubmed: 9952424google scholar: lookup
        30. Cheng FC, Kuo JS, Chia LG, Dryhurst G. Elevated 5-S-cysteinyldopamine/homovanillic acid ratio and reduced homovanillic acid in cerebrospinal fluid: possible markers for and potential insights into the pathoetiology of Parkinson's disease. J Neural Transm (Vienna) 1996;103(4):433-46.
          doi: 10.1007/BF01276419pubmed: 9617787google scholar: lookup
        31. Rump AF, Klaus W. Cardiotoxicity of adrenochrome in isolated rabbit hearts assessed by epicardial NADH fluorescence. Arch Toxicol 1994;68(9):571-5.
          doi: 10.1007/s002040050116pubmed: 7998824google scholar: lookup
        32. Fornstedt B, Carlsson A. A marked rise in 5-S-cysteinyl-dopamine levels in guinea-pig striatum following reserpine treatment. J Neural Transm 1989;76(2):155-61.
          doi: 10.1007/BF01578755pubmed: 2496196google scholar: lookup
        Subscribe to our newsletter
        Join 99,359 horse owners like you who receive our email updates on horse health and nutrition.