Regeneration of ergothioneine after reaction with singlet oxygen
Abstract
Ergothioneine (ET), an imidazole-2-thione derivative of histidine betaine, is generally considered an antioxidant. Important antioxidants are typically regenerated from their oxidized products, to prevent the interceptors from being lost after a single chemical reaction with a reactive oxygen species. However, no mechanism for the complete regeneration of ET has yet been uncovered. Here we define a non-enzymatic multi-step cycle for the regeneration of ET after reaction with singlet oxygen (1 O 2). All reaction steps were verified by density functional theory computations. Four molecules of GSH are used per turn to detoxify 1 O 2 to water. Pure 1 O 2 was generated by thermolysis at 37 °C of the endoperoxide DHPNO 2. Addition of 1 mM ET to 10 mM DHPNO 2 and 10 mM GSH increased the production of oxidized GSH (GSSG), measured by LC-MS/MS, by a factor of 26 (water) and 28 (D 2 O), respectively. In the same assay, the ring of ET alone was able to drive the cycle at equal speed; thus, the zwitterionic amino acid backbone was not involved. Our data suggest that ET reacts at least 4-fold faster with 1 O 2 than ascorbic acid. ET must now be viewed as tightly linked with the GSH/GSSG redox couple. The necessary thiol foundation is present in all mammalian and vertebrate cells, and also in all species that generate ET, such as cyanobacteria, mycobacteria, and fungi. Regeneration provides a decisive advantage for ET over other reactive, but non-recoverable, compounds. Our findings substantiate the importance of ET for the eradication of noxious 1 O 2.
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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 [233]
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- Authors
- Oumari, M., Goldfuss, B., Stoffels, C., Schmalz, H.-G., & Gründemann, D.
- Affiliations
- University of Cologne (DE)
- Corresponding author
- Gründemann, Dirk
- Venue
- Free Radical Biology and Medicine
- Publisher
- Elsevier BV
- Published
- 2019-04
- Volume
- 134
- Pages
- 498-504
- ISSN
- 0891-5849 (ISSN-L)
- OpenAlex
- W2911430216
- Cited by
- 39
- References
- 41
- Citations by year
- 2026: 6 · 2025: 2 · 2024: 5 · 2023: 8 · 2022: 2 · 2021: 8 · 2020: 6 · 2019: 2
- FWCI
- 1.49
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Free Radical Biology and Medicine (publishedVersion)
- PubMed (publishedVersion)
- Kölner Universitäts PublikationsServer (Universität zu Köln) (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Sulfur Compounds in Biology
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Keywords
- ergothioneine, singlet oxygen, antioxidant regeneration, glutathione, glutathione disulfide, reactive oxygen species scavenging
- MeSH terms
- Antioxidants, Ergothioneine, Glutathione, Oxidation-Reduction, Reactive Oxygen Species, Singlet Oxygen
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