Free radical oxidation of polyunsaturated lipids: new mechanistic insights and the development of peroxyl radical clocks
Open accessAbstract
The peroxidation of lipids in biological membranes has been implicated in both the onset and development of most degenerative diseases. The primary products of this autoxidation process are usually lipid hydroperoxides. They form as a consequence of a free radical chain reaction: lipid peroxyl radicals propagate the chain by rate-limiting H-atom abstraction from another lipid. Studies of the mechanism of lipid peroxidation are a specific part of a wider effort to understand the more general phenomenon of hydrocarbon autoxidation, which dates back some 70 years. However, the autoxidation of lipids is generally much more complicated than that of other hydrocarbons because of additional reaction pathways afforded by a variety of uniquely positioned unsaturated bonds. Indeed, polyunsaturation is an important aspect of many of the most relevant of physiological lipids, such as linoleate and arachidonate. In this Account, we present our current understanding of the mechanism of unsaturated lipid peroxidation, effectively updating our Account on the same topic published 25 years ago. Our more recent work has, in large part, been stimulated by the discovery of the nonconjugated linoleate hydroperoxide as a product under certain autoxidation conditions. The identification of this long-elusive bis-allylic hydroperoxide prompted our kinetic characterization of the reaction leading to its formation. The product distributions obtained from autoxidations of newly synthesized model compounds, which vary in either the substitution of the bis-allylic moiety or the configuration of the double bonds, have provided key insights into the overall mechanism. These insights have in turn been reinforced by the results of theoretical calculations. The picture that emerges is one wherein the delocalized carbon-centered radicals, which arise as intermediates in these reactions, first associate with dioxygen to form pre-reaction complexes. These complexes then collapse through transition state structures that maximize the orbital interactions between the delocalized radical SOMO and dioxygen. The energies of these transition states are influenced by steric effects; thus, there are distinct changes in product distribution in the autoxidation of dienes having different substitution patterns. The radical-dioxygen complexes are also intermediates in the isomerization of allylperoxyl and pentadienylperoxyls, helping explain the high regio- and stereochemical fidelity of these processes. We have taken advantage of the rapid fragmentation of nonconjugated peroxyl radicals to develop a powerful peroxyl radical clock methodology, which can be used to determine rate constants for reactions of peroxyl radicals with molecules having rate constants ranging from 1 to 10(7) M(-1) s(-1). We can make use of this methodology to address various questions, both fundamental and applied, relating to lipid peroxidation and its inhibition by radical-trapping antioxidants.
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Divalent metals, especially Fe(II), greatly speed up lipid peroxidation.
“This peroxidation reaction is dramatically accelerated by divalent metals, especially Fe(II) [7].”
From Ferroptosis: Death by Lipid Peroxidation (2016) · cites this paper as [7]
Membrane polyunsaturated lipids containing bis-allylic carbons are highly vulnerable to peroxidation when oxygen is present.
“The emergence of copious amounts of oxygen in the atmosphere was challenging for organisms with membranes having polyunsaturated lipids that contain bis-allylic carbons, because these are highly susceptible to lipid peroxidation in the presence of oxygen [7].”
From Ferroptosis: Death by Lipid Peroxidation (2016) · cites this paper as [7]
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- Authors
- Pratt, D. A., Tallman, K. A., & Porter, N. A.
- Affiliations
- University of Ottawa (CA)
- Vanderbilt University (US)
- Corresponding author
- Porter, Ned A.
- Venue
- Accounts of Chemical Research
- Publisher
- American Chemical Society (ACS)
- Published
- 2011-04-12
- Volume
- 44
- Issue
- 6
- Pages
- 458-467
- ISSN
- 0001-4842 (ISSN-L)
- 1520-4898
- PMC
- PMC3124811
- OpenAlex
- W2046658835
- Cited by
- 352
- References
- 38
- Citations by year
- 2026: 35 · 2025: 30 · 2024: 28 · 2023: 28 · 2022: 30 · 2021: 25 · 2020: 29 · 2019: 24 · 2018: 17 · 2017: 24 · 2016: 10 · 2015: 18 · 2014: 20 · 2013: 16 · 2012: 15
- FWCI
- 8.11
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- Accounts of Chemical Research (publishedVersion)
- PubMed (publishedVersion)
- PubMed Central (acceptedVersion)
- Funders
- National Institute of Environmental Health Sciences (ES013125, P01ES013125)
- Eunice Kennedy Shriver National Institute of Child Health and Human Development (R01HD064727, HD064727)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Health Sciences › Medicine › Biochemistry › Antioxidant Activity and Oxidative Stress
- Physical Sciences › Chemistry › Organic Chemistry › Edible Oils Quality and Analysis
- Keywords
- lipid peroxidation, peroxy radicals, lipid hydroperoxides, pre-reaction complex, transition state, steric effects, regioselectivity, stereochemistry, polyunsaturated lipids, linoleic acid
- MeSH terms
- Antioxidants, Fatty Acids, Unsaturated, Free Radicals, Models, Molecular, Oxidation-Reduction, Peroxides, Lipid Peroxidation, Neurodegenerative Diseases
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