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N1-acetyl-N2-formyl-5-methoxykynuramine, a biogenic amine and melatonin metabolite, functions as a potent antioxidant.
FASEB J. 2001 Oct; 15(12):2294-6.FJ

Abstract

The biogenic amine The biogenic amine N1-acetyl-N2-formyl-5-methoxykynuramine (AFMK) was investigated for its potential antioxidative capacity. AFMK is a metabolite generated through either an enzymatic or a chemical reaction pathway from melatonin. The physiological function of AFMK remains unknown. To our knowledge, this report is the first to document the potent antioxidant action of this biogenic amine. Cyclic voltammetry (CV) shows that AFMK donates two electrons at potentials of 456 mV and 668 mV, and therefore it functions as a reductive force. This function contrasts with all other physiological antioxidants that donate a single electron only when they neutralize free radicals. AFMK reduced 8-hydroxydeoxyguanosine formation induced by the incubation of DNA with oxidants significantly. Lipid peroxidation resulting from free radical damage to rat liver homogenates was also prevented by the addition of AFMK. The inhibitory effects of AFMK on both DNA and lipid damage appear to be dose-response related. In cell culture, AFMK efficiently reduced hippocampal neuronal death induced by either hydrogen peroxide, glutamate, or amyloid b25-35 peptide. AFMK is a naturally occurring molecule with potent free radical scavenging capacity (donating two electrons/molecule) and thus may be a valuable new antioxidant for preventing and treating free radical-related disorders.

Authors+Show Affiliations

Tan DX
Department of Cellular and Structural Biology, University of Texas Health Science Center, San Antonio, Texas 78229-3900, USA.
Manchester LC
No affiliation info available
Burkhardt S
No affiliation info available
Sainz RM
No affiliation info available
Mayo JC
No affiliation info available
Kohen R
No affiliation info available
Shohami E
No affiliation info available
Huo YS
No affiliation info available
Hardeland R
No affiliation info available
Reiter RJ
No affiliation info available

MeSH

8-Hydroxy-2'-DeoxyguanosineAmyloid beta-PeptidesAnimalsAntioxidantsCell DeathCells, CulturedChelating AgentsDeoxyguanosineFerrous CompoundsFree RadicalsGlutamic AcidHydrogen PeroxideKynuramineLipid PeroxidationLiverMelatoninMetals, HeavyModels, BiologicalNeuronsPeptide FragmentsRats

Pub Type(s)

Journal Article

Language

eng

PubMed ID

11511530

Citation

Tan, D X., et al. "N1-acetyl-N2-formyl-5-methoxykynuramine, a Biogenic Amine and Melatonin Metabolite, Functions as a Potent Antioxidant." FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology, vol. 15, no. 12, 2001, pp. 2294-6.
Tan DX, Manchester LC, Burkhardt S, et al. N1-acetyl-N2-formyl-5-methoxykynuramine, a biogenic amine and melatonin metabolite, functions as a potent antioxidant. FASEB J. 2001;15(12):2294-6.
Tan, D. X., Manchester, L. C., Burkhardt, S., Sainz, R. M., Mayo, J. C., Kohen, R., Shohami, E., Huo, Y. S., Hardeland, R., & Reiter, R. J. (2001). N1-acetyl-N2-formyl-5-methoxykynuramine, a biogenic amine and melatonin metabolite, functions as a potent antioxidant. FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology, 15(12), 2294-6.
Tan DX, et al. N1-acetyl-N2-formyl-5-methoxykynuramine, a Biogenic Amine and Melatonin Metabolite, Functions as a Potent Antioxidant. FASEB J. 2001;15(12):2294-6. PubMed PMID: 11511530.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - N1-acetyl-N2-formyl-5-methoxykynuramine, a biogenic amine and melatonin metabolite, functions as a potent antioxidant. AU - Tan,D X, AU - Manchester,L C, AU - Burkhardt,S, AU - Sainz,R M, AU - Mayo,J C, AU - Kohen,R, AU - Shohami,E, AU - Huo,Y S, AU - Hardeland,R, AU - Reiter,R J, Y1 - 2001/08/17/ PY - 2001/8/21/pubmed PY - 2002/1/5/medline PY - 2001/8/21/entrez SP - 2294 EP - 6 JF - FASEB journal : official publication of the Federation of American Societies for Experimental Biology JO - FASEB J VL - 15 IS - 12 N2 - The biogenic amine The biogenic amine N1-acetyl-N2-formyl-5-methoxykynuramine (AFMK) was investigated for its potential antioxidative capacity. AFMK is a metabolite generated through either an enzymatic or a chemical reaction pathway from melatonin. The physiological function of AFMK remains unknown. To our knowledge, this report is the first to document the potent antioxidant action of this biogenic amine. Cyclic voltammetry (CV) shows that AFMK donates two electrons at potentials of 456 mV and 668 mV, and therefore it functions as a reductive force. This function contrasts with all other physiological antioxidants that donate a single electron only when they neutralize free radicals. AFMK reduced 8-hydroxydeoxyguanosine formation induced by the incubation of DNA with oxidants significantly. Lipid peroxidation resulting from free radical damage to rat liver homogenates was also prevented by the addition of AFMK. The inhibitory effects of AFMK on both DNA and lipid damage appear to be dose-response related. In cell culture, AFMK efficiently reduced hippocampal neuronal death induced by either hydrogen peroxide, glutamate, or amyloid b25-35 peptide. AFMK is a naturally occurring molecule with potent free radical scavenging capacity (donating two electrons/molecule) and thus may be a valuable new antioxidant for preventing and treating free radical-related disorders. SN - 1530-6860 UR - https://www.unboundmedicine.com/medline/citation/11511530/N1_acetyl_N2_formyl_5_methoxykynuramine_a_biogenic_amine_and_melatonin_metabolite_functions_as_a_potent_antioxidant_ L2 - https://doi.org/10.1096/fj.01-0309fje DB - PRIME DP - Unbound Medicine ER -