The Interaction of Dietary Carotenoids with Radical Species
Abstract
Dietary carotenoids react with a wide range of radicals such as CCl3O2*, RSO2*, NO2*, and various arylperoxyl radicals via electron transfer producing the radical cation of the carotenoid. Less strongly oxidizing radicals, such as alkylperoxyl radicals, can lead to hydrogen atom transfer generating the neutral carotene radical. Other processes can also arise such as adduct formation with sulphur-centered radicals. The oxidation potentials have been established, showing that, in Triton X-100 micelles, lycopene is the easiest carotenoid to oxidize to its radical cation and astaxanthin is the most difficult. The interaction of carotenoids and carotenoid radicals with other antioxidants is of importance with respect to anti- and possibly pro-oxidative reactions of carotenoids. In polar environments the vitamin E (alpha-tocopherol) radical cation is deprotonated (TOH*+ --> TO* + H+) and TO* does not react with carotenoids, whereas in nonpolar environments such as hexane, TOH*+ is converted to TOH by hydrocarbon carotenoids. However, the nature of the reaction between the tocopherol and various carotenoids shows a marked variation depending on the specific tocopherol homologue. The radical cations of the carotenoids all react with vitamin C so as to "repair" the carotenoid.
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Antioxidant properties of carotenoids are related to conjugated double bonds which can accommodate unpaired electrons and extensively delocalize them over the conjugated system of double bonds.
“The antioxidant properties of carotenoids are related to conjugated double bonds which can accommodate unpaired electrons and extensively delocalize them over the conjugated system of double bonds (Mortensen et al. 2001).”
From Reactive Oxygen Species, Toxicity, Oxidative Stress, and Antioxidants: Chronic Diseases and Aging (2023) · cites this paper as Mortensen et al. 2001
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- Authors
- Mortensen, A., Skibsted, L. H., & Truscott, T. G.
- Affiliations
- Keele University (GB)
- Corresponding author
- Truscott, T.G.
- Venue
- Archives of Biochemistry and Biophysics
- Publisher
- Elsevier BV
- Published
- 2001-01
- Volume
- 385
- Issue
- 1
- Pages
- 13-19
- ISSN
- 0003-9861 (ISSN-L)
- OpenAlex
- W1997144800
- Cited by
- 278
- References
- 38
- Citations by year
- 2026: 4 · 2025: 9 · 2024: 9 · 2023: 13 · 2022: 6 · 2021: 8 · 2020: 11 · 2019: 11 · 2018: 3 · 2017: 7 · 2016: 8 · 2015: 14 · 2014: 16 · 2013: 10 · 2012: 12
- FWCI
- 10.60
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Archives of Biochemistry and Biophysics (publishedVersion)
- PubMed (publishedVersion)
- Research at the University of Copenhagen (University of Copenhagen) (submittedVersion)
- Topics
- Health Sciences › Medicine › Biochemistry › Antioxidant Activity and Oxidative Stress
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Health Sciences › Medicine › Biochemistry › Phytochemicals and Antioxidant Activities
- Keywords
- dietary carotenoids, radical cations, electron transfer, hydrogen atom transfer, oxidation potential, lycopene, astaxanthin, Triton X-100 micelles, tocopherols, vitamin C, antioxidant interactions, pro-oxidant activity, carotenoid oxidation
- MeSH terms
- Lycopene, Adjuvants, Immunologic, Antioxidants, Carotenoids, Cations, Detergents, Diet, Electrons, Free Radicals, Kinetics, Models, Chemical, Protein Binding, Time Factors, Vitamin E, Octoxynol, beta Carotene, Xanthophylls
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