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J. Biochem, 2003, Vol. 134, No. 6 903-909
© 2003 Japanese Biochemical Society

BIOCHEMISTRY

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

Yasuhiro Kambayashi*,1,2, Shozo Tero-Kubota3, Yorihiro Yamamoto4, Masashi Kato2, Minoru Nakano1, Kunio Yagi5 and Keiki Ogino2

1 Department of Photon and Free Radical Research, Japan Immunoresearch Laboratories, 351-1 Nishiyokote-cho, Takasaki 370-0021; 2 Department of Environmental and Preventive Medicine, Graduate School of Medical Science, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-8640; 3 Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, Sendai 980-8577; 4 School of Bionics, Tokyo University of Technology, 1404-1 Katakura, Hachioji, Tokyo 192-0982; and 5 Institute of Applied Biochemistry, Yagi Memorial Park, Mitake, Gifu 505-0116

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 {alpha}-hydroxyperoxyl radical [R1R2C(OH)OO·], which decomposes into the carbocation [R1C+(OH)R2] and O2·–.

* To whom correspondence should be addressed. Tel: +81-76-265-2217, Fax: +81-76-234-4233, E-mail: kambayashi{at}pub.m.kanazawa-u.ac.jp


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