N1-acetyl-N2-formyl-5-methoxykynuramine, a biogenic amine and melatonin metabolite, functions as a potent antioxidant.

D. X. Tan, L. C. Manchester, S. Burkhardt, R. M. Sainz, J. C. Mayo, R. Kohen, E. Shohami, Y. S. Huo, R. Hardeland, Russel J Reiter

Research output: Contribution to journalArticle

221 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)2294-2296
Number of pages3
JournalThe FASEB journal : official publication of the Federation of American Societies for Experimental Biology
Volume15
Issue number12
StatePublished - 2001

Fingerprint

Biogenic Amines
Melatonin
Metabolites
Free Radicals
Antioxidants
Electrons
Lipids
Molecules
DNA
Scavenging
Cell culture
Amyloid
Oxidants
Liver
Hydrogen Peroxide
Lipid Peroxidation
DNA Damage
Cyclic voltammetry
Rats
Chemical reactions

Cite this

N1-acetyl-N2-formyl-5-methoxykynuramine, a biogenic amine and melatonin metabolite, functions as a potent antioxidant. / Tan, D. X.; Manchester, L. C.; Burkhardt, S.; Sainz, R. M.; Mayo, J. C.; Kohen, R.; Shohami, E.; Huo, Y. S.; Hardeland, R.; Reiter, Russel J.

In: The FASEB journal : official publication of the Federation of American Societies for Experimental Biology, Vol. 15, No. 12, 2001, p. 2294-2296.

Research output: Contribution to journalArticle

Tan, D. X. ; Manchester, L. C. ; Burkhardt, S. ; Sainz, R. M. ; Mayo, J. C. ; Kohen, R. ; Shohami, E. ; Huo, Y. S. ; Hardeland, R. ; Reiter, Russel J. / N1-acetyl-N2-formyl-5-methoxykynuramine, a biogenic amine and melatonin metabolite, functions as a potent antioxidant. In: The FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2001 ; Vol. 15, No. 12. pp. 2294-2296.
@article{23403b05518645af93e4af0477def8b0,
title = "N1-acetyl-N2-formyl-5-methoxykynuramine, a biogenic amine and melatonin metabolite, functions as a potent antioxidant.",
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.",
author = "Tan, {D. X.} and Manchester, {L. C.} and S. Burkhardt and Sainz, {R. M.} and Mayo, {J. C.} and R. Kohen and E. Shohami and Huo, {Y. S.} and R. Hardeland and Reiter, {Russel J}",
year = "2001",
language = "English (US)",
volume = "15",
pages = "2294--2296",
journal = "FASEB Journal",
issn = "0892-6638",
publisher = "FASEB",
number = "12",

}

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, Russel J

PY - 2001

Y1 - 2001

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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0035487508&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035487508&partnerID=8YFLogxK

M3 - Article

C2 - 11511530

AN - SCOPUS:0035487508

VL - 15

SP - 2294

EP - 2296

JO - FASEB Journal

JF - FASEB Journal

SN - 0892-6638

IS - 12

ER -