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E7521 Sigma

L-(+)-Ergothioneine

Synonym: (S)-α-Carboxy-N,N,N-trimethyl-2-mercapto-1H-imidazole-4-ethanaminium inner salt, Thioneine

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Properties

Related Categories Antioxidants and Cytoprotectants, Cell Biology, Cell Signaling and Neuroscience, Cell Stress, Nitric Oxide and Cell Stress More...
InChI Key   SSISHJJTAXXQAX-ZETCQYMHSA-N
storage temp.   −20°C

Description

Other Notes

Natural amino acid found in the fungus Claviceps purpurea

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Application

L-(+)-Ergothioneine has been used for the study of its reactivity with 2,2′- and 4,4′-dipyridyl disulphide (2-Py-S-S-2-Py and 4-Py-S-S-4-Py), for the incubation of experimental cells while performing in vitro kinase activity assays for ATM (Ataxia telangiectasia mutated) or ATR (ATM- and RAD3-related).

Biochem/physiol Actions

L-(+)-Ergothioneine (ET) has the maximum concentrations in tissues subjected to oxidative stress, with the highest being in blood, eye lens, bone marrow, semen and liver. It acts as an anti-oxidant and prevents apoptosis, by scavenging reactive oxygen and nitrogen species. The anti-oxidant activity is attributable to sulfhydryl groups. It acts as a substrate for SLC22A4 (solute carrier family 22, member 4) transporter. In alveolar macrophages, it prevents the release of interleukin-8 (IL-8) by tumor necrosis factor (TNF)α. IL-8 is an inflammatory cytokine. It also regulates the oxidative damage in liver and kidneys, and has a protective action against lipid peroxidation. It is also responsible for the conservation of endogenous glutathione and α-tocopherol. In UV-irradiated human dermal fibroblasts, it scavenges reactive oxygen species (ROS), and suppresses matrix metalloproteinases 1 (MMP1) expression. It might also have anti-ageing effects on skin caused by UV-radiation.

General description

L-(+)-Ergothioneine (ET) is a sulfur-containing amino acid, which is only produced by Actinomycetales bacteria and non-yeast like fungi belonging to the division Basidiomycota and Ascomycota. It was originally isolated from Claviceps purpurea or rye ergot. It is obtained from L-histidine, which is converted into betaine form called hercynine. It is found in both animals and plants, and mammals usually obtain it from their diet, e.g. through mushrooms or oats. It is tautomeric in nature, and in neutral aqueous solution exists in thione form.

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Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles
Peer-Reviewed Papers
15

References

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