A mushroom-derived amino acid, ergothioneine, is a potential inhibitor of inflammation-related DNA halogenation

Asahi, Takashi; Wu, Xiaohong; Shimoda, Hiroshi; Hisaka, Shinsuke; Harada, Eijiro; Kanno, Tomomi; Nakamura, Yoshimasa; Kato, Yoji; Osawa, Toshihiko

doi:10.1080/09168451.2015.1083396

Cited by 45 publications

(29 citation statements)

References 20 publications

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“…In evaluating the antioxidant potency of ERG or anything else, it is molecules such as these that are normally assessed. Although the literature is somewhat scattered and heterogeneous, it seems clear that as well as hydroxyl radicals (228)(229)(230)(231)(232) , ERG can also react with and detoxify, or prevent the formation of, singlet oxygen (233)(234)(235)(236)(237)(238)(239)(240)(241)(242) , ozone (243) , superoxide (231,241,(244)(245)(246) , peroxide (32,124,247,248) , hypochlorite (32,232,249) and peroxynitrite (224,231,250,251) . Consequently, it is a potent antioxidant.…”

Section: Oxidative Stressmentioning

confidence: 99%

The biology of ergothioneine, an antioxidant nutraceutical

et al. 2020

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Ergothioneine (ERG) is an unusual thio-histidine betaine amino acid that has potent antioxidant activities. It is synthesised by a variety of microbes, especially fungi (including in mushroom fruiting bodies) and actinobacteria, but is not synthesised by plants and animals who acquire it via the soil and their diet, respectively. Animals have evolved a highly selective transporter for it, known as solute carrier family 22, member 4 (SLC22A4) in humans, signifying its importance, and ERG may even have the status of a vitamin. ERG accumulates differentially in various tissues, according to their expression of SLC22A4, favouring those such as erythrocytes that may be subject to oxidative stress. Mushroom or ERG consumption seems to provide significant prevention against oxidative stress in a large variety of systems. ERG seems to have strong cytoprotective status, and its concentration is lowered in a number of chronic inflammatory diseases. It has been passed as safe by regulatory agencies, and may have value as a nutraceutical and antioxidant more generally.

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Section: Oxidative Stressmentioning

confidence: 99%

The biology of ergothioneine, an antioxidant nutraceutical

et al. 2020

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“…Several types of evidence imply that it has an important role in vivo as a natural antioxidant [50][51][52]. First this activity may be measured directly [53][54][55]. Secondly, decreasing it leads to the accumulation of the products of the interaction of macromolecules with hydroxyl radicals [56][57][58] and a decreased lifespan in model organisms [59].…”

Section: Some Mammalian Transporters With Known Selectivity For Exogementioning

confidence: 99%

Consensus rank orderings of molecular fingerprints illustrate the most genuine similarities between marketed drugs and small endogenous human metabolites, but highlight exogenous natural products as the most important ‘natural’ drug transporter substrates

O’Hagan¹,

Kell

2017

ADMET DMPK

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We compare several molecular fingerprint encodings for marketed, small molecule drugs, and assess how their rank order varies with the fingerprint in terms of the Tanimoto similarity to the most similar endogenous human metabolite as taken from Recon2. For the great majority of drugs, the rank order varies very greatly depending on the encoding used, and also somewhat when the Tanimoto similarity (TS) is replaced by the Tversky similarity. However, for a subset of such drugs, amounting to some 10 % of the set and a Tanimoto similarity of ~0.8 or greater, the similarity coefficient is relatively robust to the encoding used. This leads to a metric that, while arbitrary, suggests that a Tanimoto similarity of 0.75-0.8 or greater genuinely does imply a considerable structural similarity of two molecules in the drug-endogenite space. Although comparatively few (<10 % of) marketed drugs are, in this sense, robustly similar to an endogenite, there is often at least one encoding with which they are genuinely similar (e.g. TS > 0.75). This is referred to as the Take Your Pick Improved Cheminformatic Analytical Likeness or TYPICAL encoding, and on this basis some 66 % of drugs are within a TS of 0.75 to an endogenite.We next explicitly recognise that natural evolution will have selected for the ability to transport dietary substances, including plant, animal and microbial ‘secondary’ metabolites, that are of benefit to the host. These should also be explored in terms of their closeness to marketed drugs. We thus compared the TS of marketed drugs with the contents of various databases of natural products. When this is done, we find that some 80 % of marketed drugs are within a TS of 0.7 to a natural product, even using just the MACCS encoding. For patterned and TYPICAL encodings, 80 % and 98 % of drugs are within a TS of 0.8 to (an endogenite or) an exogenous natural product. This implies strongly that it is these exogeneous (dietary and medicinal) natural products that are more to be seen as the ‘natural’ substrates of drug transporters (as is recognised, for instance, for the solute carrier SLC22A4 and ergothioneine). This novel analysis casts an entirely different light on the kinds of natural molecules that are to be seen as most like marketed drugs, and hence potential transporter substrates, and further suggests that a renewed exploitation of natural products as drug scaffolds would be amply rewarded.

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“…EGT rich Coprinus extract inhibited both MPO activity and HOBr-induced DNA damage by measuring 8-BrdG formation in vivo in addition to inhibition of UV-B-induced inflammatory responses. The HOBr scavenging effect of EGT was also found to be higher than those of ascorbic acid and glutathione [43].…”

Section: Application Of Oxidative Stress Biomarkers For Functional Fomentioning

confidence: 84%

Development and application of oxidative stress biomarkers

Osawa

2018

Bioscience, Biotechnology, and Biochemistry

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Oxidative stress may cause a wide variety of free radical reactions to produce deleterious modifications in membranes, proteins, enzymes, and DNA. Reactive Oxygen Species (ROS) generated by myeloperoxidase (MPO) can induce lipid peroxidation and also play an important role in the generation of reactive chlorinating and brominating species. As the universal biomarkers, chemical, and immunochemical approach on oxidatively modified and halogenated tyrosines has been carried out. As amido-type adduct biomarkers, chemical, and immunochemical evaluation of hexanoyl- and propanoyl-lysines, hexanoyl- and propanoyl-dopamines and phospholipids were prepared and developed for application of evaluation of novel antioxidative functional food factors. We have also involved in application of oxidatively modified DNAs such as 8-hydroxy- and 8-halogenated deoxyguanosines as the useful biomarkers for age-related diseases using both in vitro and in vivo systems. Application of these oxidative stress biomarkers for novel type of functional food development and recent approach for development of novel evaluation systems are also discussed.

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A mushroom-derived amino acid, ergothioneine, is a potential inhibitor of inflammation-related DNA halogenation

Cited by 45 publications

References 20 publications

The biology of ergothioneine, an antioxidant nutraceutical

The biology of ergothioneine, an antioxidant nutraceutical

Consensus rank orderings of molecular fingerprints illustrate the most genuine similarities between marketed drugs and small endogenous human metabolites, but highlight exogenous natural products as the most important ‘natural’ drug transporter substrates

Development and application of oxidative stress biomarkers

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