Formation of Superoxide Anion during Ferrous Ion-Induced Decomposition of Linoleic Acid Hydroperoxide under Aerobic Conditions

Yasuhiro Kambayashi, Shozo Tero-Kubota, Yorihiro Yamamoto, Masashi Kato, Minoru Nakano, Kunio Yagi, Keiki Ogino

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

We studied the mechanism of formation of oxygen radicals during ferrous ion-induced decomposition of linoleic acid hydroperoxide using the spin trapping and chemiluminescence methods. The formation of the superoxide anion (O2.-) was verified in the present study. The hydroxyl radical is also generated through Fenton type decomposition of hydrogen peroxide produced on disproportionation of O2.-. A carbon-centered radical was detected using 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide (DEPMPO) as a spin trap. Alkoxyl radical formation is essential for the conversion of linoleic acid hydroperoxide into the peroxyl radical by ferrous ion. It is likely that the alkoxyl radical [R1CH(O.)R2] is converted into the hydroxylcarbon radical [R1C.(OH)R2] in water, and that this carbon radical reacts with oxygen to give the α-hydroxyperoxyl radical [R1R2C(OH)OO.], which decomposes into the carbocation [R1C+(OH)R 2] and O2.-.

Original languageEnglish
Pages (from-to)903-909
Number of pages7
JournalJournal of Biochemistry
Volume134
Issue number6
DOIs
Publication statusPublished - Dec 2003
Externally publishedYes

Fingerprint

Superoxides
Carbon
Ions
Decomposition
Spin Trapping
Chemiluminescence
Luminescence
Hydroxyl Radical
Hydrogen Peroxide
Reactive Oxygen Species
Oxygen
Water
linoleic acid hydroperoxide
alkoxyl radical
5-diethoxyphosphoryl-5-methyl-1-pyrroline N-oxide
perhydroxyl radical

Keywords

  • Ferrous ion-induced decomposition of linoleic acid hydroperoxide
  • Hydrogen peroxide
  • Hydroxyl radical
  • Linoleic acid alkoxyl radical
  • Superoxide anion

ASJC Scopus subject areas

  • Biochemistry

Cite this

Formation of Superoxide Anion during Ferrous Ion-Induced Decomposition of Linoleic Acid Hydroperoxide under Aerobic Conditions. / Kambayashi, Yasuhiro; Tero-Kubota, Shozo; Yamamoto, Yorihiro; Kato, Masashi; Nakano, Minoru; Yagi, Kunio; Ogino, Keiki.

In: Journal of Biochemistry, Vol. 134, No. 6, 12.2003, p. 903-909.

Research output: Contribution to journalArticle

Kambayashi, Y, Tero-Kubota, S, Yamamoto, Y, Kato, M, Nakano, M, Yagi, K & Ogino, K 2003, 'Formation of Superoxide Anion during Ferrous Ion-Induced Decomposition of Linoleic Acid Hydroperoxide under Aerobic Conditions', Journal of Biochemistry, vol. 134, no. 6, pp. 903-909. https://doi.org/10.1093/jb/mvg217
Kambayashi, Yasuhiro ; Tero-Kubota, Shozo ; Yamamoto, Yorihiro ; Kato, Masashi ; Nakano, Minoru ; Yagi, Kunio ; Ogino, Keiki. / Formation of Superoxide Anion during Ferrous Ion-Induced Decomposition of Linoleic Acid Hydroperoxide under Aerobic Conditions. In: Journal of Biochemistry. 2003 ; Vol. 134, No. 6. pp. 903-909.
@article{82f74ab0fab048208f9d5a318da38d39,
title = "Formation of Superoxide Anion during Ferrous Ion-Induced Decomposition of Linoleic Acid Hydroperoxide under Aerobic Conditions",
abstract = "We studied the mechanism of formation of oxygen radicals during ferrous ion-induced decomposition of linoleic acid hydroperoxide using the spin trapping and chemiluminescence methods. The formation of the superoxide anion (O2.-) was verified in the present study. The hydroxyl radical is also generated through Fenton type decomposition of hydrogen peroxide produced on disproportionation of O2.-. A carbon-centered radical was detected using 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide (DEPMPO) as a spin trap. Alkoxyl radical formation is essential for the conversion of linoleic acid hydroperoxide into the peroxyl radical by ferrous ion. It is likely that the alkoxyl radical [R1CH(O.)R2] is converted into the hydroxylcarbon radical [R1C.(OH)R2] in water, and that this carbon radical reacts with oxygen to give the α-hydroxyperoxyl radical [R1R2C(OH)OO.], which decomposes into the carbocation [R1C+(OH)R 2] and O2.-.",
keywords = "Ferrous ion-induced decomposition of linoleic acid hydroperoxide, Hydrogen peroxide, Hydroxyl radical, Linoleic acid alkoxyl radical, Superoxide anion",
author = "Yasuhiro Kambayashi and Shozo Tero-Kubota and Yorihiro Yamamoto and Masashi Kato and Minoru Nakano and Kunio Yagi and Keiki Ogino",
year = "2003",
month = "12",
doi = "10.1093/jb/mvg217",
language = "English",
volume = "134",
pages = "903--909",
journal = "Journal of Biochemistry",
issn = "0021-924X",
publisher = "Oxford University Press",
number = "6",

}

TY - JOUR

T1 - Formation of Superoxide Anion during Ferrous Ion-Induced Decomposition of Linoleic Acid Hydroperoxide under Aerobic Conditions

AU - Kambayashi, Yasuhiro

AU - Tero-Kubota, Shozo

AU - Yamamoto, Yorihiro

AU - Kato, Masashi

AU - Nakano, Minoru

AU - Yagi, Kunio

AU - Ogino, Keiki

PY - 2003/12

Y1 - 2003/12

N2 - We studied the mechanism of formation of oxygen radicals during ferrous ion-induced decomposition of linoleic acid hydroperoxide using the spin trapping and chemiluminescence methods. The formation of the superoxide anion (O2.-) was verified in the present study. The hydroxyl radical is also generated through Fenton type decomposition of hydrogen peroxide produced on disproportionation of O2.-. A carbon-centered radical was detected using 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide (DEPMPO) as a spin trap. Alkoxyl radical formation is essential for the conversion of linoleic acid hydroperoxide into the peroxyl radical by ferrous ion. It is likely that the alkoxyl radical [R1CH(O.)R2] is converted into the hydroxylcarbon radical [R1C.(OH)R2] in water, and that this carbon radical reacts with oxygen to give the α-hydroxyperoxyl radical [R1R2C(OH)OO.], which decomposes into the carbocation [R1C+(OH)R 2] and O2.-.

AB - We studied the mechanism of formation of oxygen radicals during ferrous ion-induced decomposition of linoleic acid hydroperoxide using the spin trapping and chemiluminescence methods. The formation of the superoxide anion (O2.-) was verified in the present study. The hydroxyl radical is also generated through Fenton type decomposition of hydrogen peroxide produced on disproportionation of O2.-. A carbon-centered radical was detected using 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide (DEPMPO) as a spin trap. Alkoxyl radical formation is essential for the conversion of linoleic acid hydroperoxide into the peroxyl radical by ferrous ion. It is likely that the alkoxyl radical [R1CH(O.)R2] is converted into the hydroxylcarbon radical [R1C.(OH)R2] in water, and that this carbon radical reacts with oxygen to give the α-hydroxyperoxyl radical [R1R2C(OH)OO.], which decomposes into the carbocation [R1C+(OH)R 2] and O2.-.

KW - Ferrous ion-induced decomposition of linoleic acid hydroperoxide

KW - Hydrogen peroxide

KW - Hydroxyl radical

KW - Linoleic acid alkoxyl radical

KW - Superoxide anion

UR - http://www.scopus.com/inward/record.url?scp=1342283141&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=1342283141&partnerID=8YFLogxK

U2 - 10.1093/jb/mvg217

DO - 10.1093/jb/mvg217

M3 - Article

C2 - 14769880

AN - SCOPUS:1342283141

VL - 134

SP - 903

EP - 909

JO - Journal of Biochemistry

JF - Journal of Biochemistry

SN - 0021-924X

IS - 6

ER -