One-electron oxidation of ergothioneine and analogues investigated by pulse radiolysis: redox reaction involving ergothioneine and vitamin C
Open accessAbstract
Redox reactions of endogenous and exogenous sulphur-containing compounds are involved in protection against oxidative damage arising from the incidence and/or treatment of many diseases, including cancer. We have investigated, via pulse radiolysis, the one-electron oxidation of ergothioneine, a molecule with antioxidant properties which is detected at millimolar concentrations in certain tissues and fluids subject to oxidative stress, including erythrocytes and plasma. The spectrum of the transient species, assigned to the product of one-electron oxidation, observed after reaction of ergothioneine with the oxidizing radicals OH•, N3• and CCl3O2• has a maximum absorption at 520 nm and is very similar to that obtained by oxidation of analogous molecules such as 2-mercaptoimidazole, 1-methyl-2-mercaptoimidazole, S-methyl- and S,N-dimethyl-ergothioneine. In the presence of vitamin C, the oxidized form of ergothioneine is repaired by a rapid reduction (k = 6.3×108 M-1·s-1) producing ascorbyl radicals. This co-operative interaction between ergothionine and ascorbate, similar to that previously observed between vitamin E and ascorbate, may contribute to essential biological redox protection.
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
ERG can react with and detoxify, or prevent the formation of, hydroxyl radicals, singlet oxygen, ozone, superoxide, peroxide, hypochlorite and peroxynitrite.
“Although the literature is somewhat scattered and heterogeneous, it seems clear that as well as hydroxyl radicals(228–232), ERG can also react with and detoxify, or prevent the formation of, singlet oxygen(233–242), ozone(243), superoxide(231,241,244–246), peroxide(32,124,247,248), hypochlorite(32,232,249) and peroxynitrite(224,231,250,251).”
From The biology of ergothioneine, an antioxidant nutraceutical (2020) · cites this paper as [229]
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Cites
The antioxidant action of ergothioneine
Akanmu, D., Cecchini, R., Aruoma, O. I., & Halliwell, B. (1991) · Archives of Biochemistry and Biophysics · doi:10.1016/0003-9861(91)90158-f · Cited by 251 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
The biology of ergothioneine, an antioxidant nutraceutical
Borodina, I., Kenny, L. C., McCarthy, C. M., Paramasivan, K., Pretorius, E., Roberts, T. J., van der Hoek, S. A., & Kell, D. B. (2020) · Nutrition Research Reviews · doi:10.1017/s0954422419000301 · Cited by 296 · see citing works
Fahey, R. C. (2001) · Annual Review of Microbiology · doi:10.1146/annurev.micro.55.1.333 · Cited by 266 · see citing works
Ergothioneine, an adaptive antioxidant for the protection of injured tissues? A hypothesis
Halliwell, B., Cheah, I. K., & Drum, C. L. (2016) · Biochemical and Biophysical Research Communications · doi:10.1016/j.bbrc.2015.12.124 · Cited by 123 · see citing works
Zhu, B.-Z., Mao, L., Fan, R.-M., Zhu, J.-G., Zhang, Y.-N., Wang, J., Kalyanaraman, B., & Frei, B. (2011) · Chemical Research in Toxicology · doi:10.1021/tx100214t · Cited by 122 · see citing works
- Authors
- ASMUS, K.-D., BENSASSON, R. V., BERNIER, J.-L., HOUSSIN, R., & LAND, E. J.
- Affiliations
- University of Notre Dame (US)
- Muséum national d'Histoire naturelle (FR)
- Institute de Chimie Pharmaceutique, rue du Professor Laguesse, 59045 Lille Cedex, France
- Cancer Research UK Manchester Institute (GB)
- Venue
- Biochemical Journal
- Publisher
- Portland Press Ltd.
- Published
- 1996-04-15
- Volume
- 315
- Issue
- 2
- Pages
- 625-629
- ISSN
- 0264-6021 (ISSN-L)
- 1470-8728
- PMC
- PMC1217242
- OpenAlex
- W1773776221
- Cited by
- 89
- References
- 1
- Citations by year
- 2026: 5 · 2025: 2 · 2024: 4 · 2023: 4 · 2022: 4 · 2021: 2 · 2020: 2 · 2019: 9 · 2018: 2 · 2017: 3 · 2016: 4 · 2015: 4 · 2014: 6 · 2013: 1 · 2012: 5
- FWCI
- 1.50
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Locations
- Biochemical Journal (publishedVersion)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
- Health Sciences › Medicine › Biochemistry › Antioxidant Activity and Oxidative Stress
- Keywords
- ergothioneine, one-electron oxidation, vitamin C, ascorbyl radical, oxidative stress, antioxidants, sulfur compounds, 2-mercaptoimidazole, hydroxyl radicals, nitrosyl radicals, transient species
- MeSH terms
- Antioxidants, Ascorbic Acid, Azides, Carbon Tetrachloride, Dehydroascorbic Acid, Electrons, Ergothioneine, Free Radicals, Humans, Kinetics, Oxidation-Reduction, Pulse Radiolysis, Molecular Structure, Hydroxyl Radical, Oxidative Stress, In Vitro Techniques
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
