E7521

L-(+)-Ergothioneine

• Sinónimos: 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
• Fórmula empírica (notación de Hill): C₉H₁₅N₃O₂S
• Número de CAS: 497-30-3
• Peso molecular: 229.30
• Número CE: 207-843-5
• Número MDL: MFCD00167474
• Código UNSPSC: 12352209
• ID de la sustancia en PubChem: 24894650
• NACRES: NA.32

Propiedades

• origen biológico: fungus (Actinomycetales); fungus (Ascomycota); fungus (Basidiomycota)
• Ensayo: ≥98.0%
• Formulario: powder
• mol peso: 229.30
• condiciones de almacenamiento: (Keep container tightly closed in a dry and well-ventilated place)
• técnicas: protein quantification: suitable
• solubilidad: water: 50 mg/mL, clear, colorless
• temp. de almacenamiento: −20°C
• cadena SMILES: 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
• Clave InChI: SSISHJJTAXXQAX-ZETCQYMHSA-N

Descripción

Descripción general

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

Aplicación

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]

Acciones bioquímicas o fisiológicas

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]

Envase

Bottomless glass bottle. Contents are inside inserted fused cone.

Otras notas

Natural amino acid found in the fungus Claviceps purpurea

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable
• Equipo de protección personal: Eyeshields, Gloves, type N95 (US)