E7521

L-(+)-Ergothioneine

• Synonym(s): 2-mercaptohistidine trimethyl betaine, Ergothioneine, Sympectothion, Thiasine, Thiolhistidine-betaine, Thioneine, (S)-α-Carboxy-N,N,N-trimethyl-2-mercapto-1H-imidazole-4-ethanaminium inner salt
• Empirical Formula (Hill Notation): C₉H₁₅N₃O₂S
• CAS Number: 497-30-3
• Molecular Weight: 229.30
• EC Number: 207-843-5
• MDL number: MFCD00167474
• UNSPSC Code: 12352209
• PubChem Substance ID: 24894650
• NACRES: NA.32

Properties

• biological source: fungus (Actinomycetales); fungus (Ascomycota); fungus (Basidiomycota)
• Quality Level: 200
• assay: ≥98.0%
• form: powder
• mol wt: 229.30
• storage condition: (Keep container tightly closed in a dry and well-ventilated place)
• technique(s): protein quantification: suitable
• solubility: water: 50 mg/mL, clear, colorless
• storage temp.: −20°C
• SMILES string: C[N+](C)(C)[C@@H](Cc1c[nH]c(S)n1)C([O-])=O
• InChI: 1S/C9H15N3O2S/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/m0/s1
• InChI key: SSISHJJTAXXQAX-ZETCQYMHSA-N

Description

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.[1]

Research area: Apoptosis

Application

L-(+)-Ergothioneine is suitable for use in 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).[2] It may also be used for the incubation of experimental cells while performing in vitro kinase activity assays for ATM (Ataxia telangiectasia mutated) or ATR (ATM- and RAD3-related).[3]
L-(+)-Ergothioneine has been used:

• as a component of the maturation medium for cumulus-oocyte complexes (COCs) to test protective function on lipid peroxide formation[4]
• as an antioxidant compound to test type 2 diabetes patients[5]
• as a positive control in solute carrier protein 22 A4 (SLC22A4) transport assay[6]

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.[1] 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.[7] ET being an antioxidant, protects against γ and UV radiation. 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.[8]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Natural amino acid found in the fungus Claviceps purpurea

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)