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Perhydroxyl radical (HOO.) initiated lipid peroxidation. The role of fatty acid hydroperoxides
Open accessAbstract
It is demonstrated that the perhydroxyl radical (HOO., the conjugate acid of superoxide (O2-], initiates fatty acid peroxidation (a model for biological lipid peroxidation) by two parallel pathways: fatty acid hydroperoxide (LOOH)-independent and LOOH-dependent. Previous workers (Gebicki, J. M., and Bielski, B. H. J. (1981) J. Am. Chem. Soc. 103, 7020-7025) demonstrated that HOO., generated by pulse radiolysis, initiates peroxidation in ethanol/water fatty acid dispersions by abstraction of the bis-allylic hydrogen atom from a polyunsaturated fatty acid. Addition of O2 to the fatty acid radicals forms peroxyl radicals (LOO.s), the chain-propagating species of lipid peroxidation. In this work it is demonstrated that HOO., generated either chemically (KO2) or enzymatically (xanthine oxidase), is a good initiator of fatty acid peroxidation in linoleic acid ethanol/water dispersions; O2- serves only as the source of HOO., and HOO. initiation can be observed at physiologically relevant pH values. In contrast to the previous results, the initiating effectiveness of HOO. is related directly to the initial concentrations of LOOHs in the lipids to be peroxidized. This defines a LOOH-dependent mechanism for fatty acid peroxidation initiation by HOO., which parallels the previously established LOOH-independent pathway. Since the LOOH-dependent pathway is much more facile than the LOOH-independent pathway, LOOH is the kinetically preferred site of HOO. attack in these systems. Experiments comparing HOO./LOOH-dependent fatty acid peroxidation with transition metal- and peroxyl radical-initiated peroxidation rule out the participation of the latter two species as initiators, which defines the HOO./LOOH initiation system as mechanistically unique. LOOH product studies are consistent with either a direct or indirect hydrogen atom transfer between LOOH and HOO. to yield LOO.s, which propagate peroxidation. The LOOH-dependent pathway of HOO.-initiated fatty acid peroxidation may be relevant to mechanisms of lipid peroxidation initiation in vivo.
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“The superoxide radical is the conjugate base of a weak acid, the hydroperoxide radical HOO•, whose pKa is 4.88 [18].”
From Superoxide Anion Chemistry—Its Role at the Core of the Innate Immunity (2023) · cites this paper as [18]
In the citing paper
“Superoxide can also become protonated to form the hydroperoxyl radical that can promote lipid peroxidation (7) and subsequent oxidative modification of proteins, low-molecular-weight thiols, and membrane lipids.”
From Redox regulation of mitochondrial function (2012) · cites this paper as [7]
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Metadata
- Authors
- Aikens, J., & Dix, T. A.
- Affiliations
- University of California, Irvine (US)
- ORCID
- Dix, T.A.
- Venue
- Journal of Biological Chemistry
- Publisher
- Elsevier BV
- Published
- 1991-08
- Volume
- 266
- Issue
- 23
- Pages
- 15091-15098
- ISSN
- 0021-9258 (ISSN-L)
- OpenAlex
- W1574445997
- Cited by
- 228
- References
- 44
- Citations by year
- 2026: 9 · 2025: 9 · 2024: 5 · 2023: 4 · 2022: 7 · 2021: 4 · 2020: 4 · 2019: 8 · 2018: 3 · 2017: 10 · 2016: 9 · 2015: 8 · 2014: 5 · 2013: 11 · 2012: 10
- FWCI
- 3.50
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- Locations
- Journal of Biological Chemistry (publishedVersion, cc-by)
- PubMed (publishedVersion)
- Funders
- National Institutes of Health (5r01gm040338-06)
- National Institute of General Medical Sciences (GM-40338)
- Topics
- Health Sciences › Medicine › Biochemistry (medical) › Antioxidant Activity and Oxidative Stress
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
- Keywords
- hydroperoxyl radical, lipid peroxidation, fatty acid hydroperoxides, linoleic acid, superoxide, xanthine oxidase, peroxy radicals, hydrogen atom transfer
- MeSH terms
- Chromatography, High Pressure Liquid, Fatty Acids, Free Radicals, Kinetics, Lipid Peroxides, Oxidation-Reduction, Lipid Peroxidation
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