One-electron oxidation of ergothioneine and analogues investigated by pulse radiolysis: redox reaction involving ergothioneine and vitamin C.
AffiliationRadiation Laboratory, University of Notre Dame, IN 46556, USA.
MetadataShow full item record
AbstractRedox 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 x 10(8) 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.
CitationOne-electron oxidation of ergothioneine and analogues investigated by pulse radiolysis: redox reaction involving ergothioneine and vitamin C. 1996, 315 ( Pt 2):625-9 Biochem. J.
JournalThe Biochemical Journal
- Heterocyclic thiols as antioxidants: why ovothiol C is a better antioxidant than ergothioneine.
- Authors: Marjanovic B, Simic MG, Jovanovic SV
- Issue date: 1995 Apr
- Ergothioneine prevents copper-induced oxidative damage to DNA and protein by forming a redox-inactive ergothioneine-copper complex.
- Authors: Zhu BZ, Mao L, Fan RM, Zhu JG, Zhang YN, Wang J, Kalyanaraman B, Frei B
- Issue date: 2011 Jan 14
- Pulse Radiolysis Studies for Mechanism in Biochemical Redox Reactions.
- Authors: Kobayashi K
- Issue date: 2019 Mar 27
- Oxidation of tetrahydrobiopterin by biological radicals and scavenging of the trihydrobiopterin radical by ascorbate.
- Authors: Patel KB, Stratford MR, Wardman P, Everett SA
- Issue date: 2002 Feb 1
- Redox reactions of tocopherol monoglucoside in aqueous solutions: a pulse radiolysis study.
- Authors: Kapoor S, Mukherjee T, Kagiya TV, Nair CK
- Issue date: 2002 Mar