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The Pecking Order of Free Radicals and Antioxidants: Lipid Peroxidation, α-Tocopherol, and Ascorbate
Abstract
Free radicals vary widely in their thermodynamic properties, ranging from very oxidizing to very reducing. These thermodynamic properties can be used to predict a pecking order, or hierarchy, for free radical reactions. Using one-electron reduction potentials, the predicted pecking order is in agreement with experimentally observed free radical electron (hydrogen atom) transfer reactions. These potentials are also in agreement with experimental data that suggest that vitamin E, the primary lipid soluble small molecule antioxidant, and vitamin C, the terminal water soluble small molecule antioxidant, cooperate to protect lipids and lipid structures against peroxidation. Although vitamin E is located in membranes and vitamin C is located in aqueous phases, vitamin C is able to recycle vitamin E; i.e., vitamin C repairs the tocopheroxyl (chromanoxyl) radical of vitamin E, thereby permitting vitamin E to function again as a free radical chain-breaking antioxidant. This review discusses: (i) the thermodynamics of free radical reactions that are of interest to the health sciences; (ii) the fundamental thermodynamic and kinetic properties that are associated with chain-breaking antioxidants; (iii) the unique interfacial nature of the apparent reaction of the tocopherol free radical (vitamin E radical) and vitamin C; and (iv) presents a hierarchy, or pecking order, for free radical electron (hydrogen atom) transfer reactions.
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“physiological ascorbate at micromolar concentrations can reduce harmful ROS9”
From Targeting cancer vulnerabilities with high-dose vitamin C (2019) · cites this paper as [9]
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“Ascorbic acid can interact with α-tocopherol at a membrane surface and converting the tocopheroxyl radical to its hydroxyl form, essentially recycling it, and the more stable ascorbyl radical (Figure 2) is enzymatically reduced [75], preventing lipid oxidation much more effectively, than in systems without ascorbic ac…”
BackgroundInfluentialPrognostic Significance of Uric Acid Serum Concentration in Patients With Acute Ischemic Stroke
Chamorro, Á., Obach, V., Cervera, Á., Revilla, M., Deulofeu, R., & Aponte, J. H. (2002) · Stroke · doi:10.1161/hs0402.105927 · Cited by 261
Vitamin C in Health and Disease: Its Role in the Metabolism of Cells and Redox State in the Brain
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“The ascorbyl radical is a relatively stable molecule with an average life of 10–5 s (Buettner, 1993; Padayatty et al., 2003).”
BackgroundAntioxidant Activity of Eugenol and Related Monomeric and Dimeric Compounds.
Ogata, M., Hoshi, M., Urano, S., & Endō, T. (2000) · Chemical and Pharmaceutical Bulletin · doi:10.1248/cpb.48.1467 · Cited by 265
Lipid oxidation and its implications to meat quality and human health
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“The hydrogen atoms of methylene groups located in between double bonds have the weakest bond energy (Buettner, 1993; Koppenol, 1990).”
BackgroundPossible Role of Oxidative Damage in Metal-Induced Carcinogenesis
Kasprzak, K. S. (1995) · Cancer Investigation · doi:10.3109/07357909509031921 · Cited by 262
Metadata
- Authors
- Buettner, G. R.
- Affiliations
- University of Iowa (US)
- Corresponding author
- Buettner, G.R.
- ORCID
- Buettner, G.R.
- Venue
- Archives of Biochemistry and Biophysics
- Publisher
- Elsevier BV
- Published
- 1993-02
- Volume
- 300
- Issue
- 2
- Pages
- 535-543
- ISSN
- 0003-9861 (ISSN-L)
- OpenAlex
- W2061242359
- Cited by
- 2,417
- References
- 0
- Citations by year
- 2026: 46 · 2025: 41 · 2024: 58 · 2023: 72 · 2022: 81 · 2021: 87 · 2020: 76 · 2019: 74 · 2018: 73 · 2017: 68 · 2016: 66 · 2015: 82 · 2014: 100 · 2013: 90 · 2012: 101
- FWCI
- 39.15
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Archives of Biochemistry and Biophysics (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Health Sciences › Medicine › Biochemistry (medical) › Antioxidant Activity and Oxidative Stress
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Health Sciences › Medicine › Biochemistry (medical) › Phytochemicals and Antioxidant Activities
- Keywords
- free radicals, pecking order, redox potential, hydrogen atom transfer, lipid peroxidation, alpha-tocopherol, vitamin E, vitamin C, tocopheroxyl radical, chain-breaking antioxidants
- MeSH terms
- Antioxidants, Ascorbic Acid, Fatty Acids, Unsaturated, Free Radicals, Kinetics, Membrane Lipids, Oxidation-Reduction, Thermodynamics, Vitamin E, Lipid Peroxidation
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