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
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About This Item
Empirical Formula (Hill Notation):
C9H15N3O2S
CAS Number:
Molecular Weight:
229.30
NACRES:
NA.32
PubChem Substance ID:
UNSPSC Code:
12352209
EC Number:
207-843-5
MDL number:
InChI key
SSISHJJTAXXQAX-ZETCQYMHSA-N
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
SMILES string
C[N+](C)(C)[C@@H](Cc1c[nH]c(S)n1)C([O-])=O
biological source
fungus (Actinomycetales)
fungus (Ascomycota)
fungus (Basidiomycota)
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
Quality Level
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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). 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).
L-(+)-Ergothioneine has been used:
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
- as an antioxidant compound to test type 2 diabetes patients
- as a positive control in solute carrier protein 22 A4 (SLC22A4) transport assay
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. 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.
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.
Research area: Apoptosis
Research area: Apoptosis
Other Notes
Natural amino acid found in the fungus Claviceps purpurea
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Monica Deiana et al.
Clinical nutrition (Edinburgh, Scotland), 23(2), 183-193 (2004-03-20)
L-ergothioneine is a fungal metabolite exhibiting antioxidant functions in cells. The aim of this study was to assess the effect of oral administration of L-ergothioneine on the oxidative damage in vivo caused by the Fenton reagent ferric-nitrilotriacetate. Rats were supplemented
J Carlsson et al.
The Biochemical journal, 139(1), 221-235 (1974-04-01)
1. The reactions of 2,2'- and 4,4'-dipyridyl disulphide (2-Py-S-S-2-Py and 4-Py-S-S-4-Py) with l-ergothioneine (2-mercapto-l-histidine betaine), 2-mercaptoimidazole, 1-methyl-2-mercaptoimidazole, thiourea, thioacetamide, 2-thiopyridone (Py-2-SH) and 4-thiopyridone (Py-4-SH) were investigated spectrophotometrically in the pH range approx. 1-9. 2. These reactions involve two sequential reversible
Irwin K Cheah et al.
Biochimica et biophysica acta, 1822(5), 784-793 (2011-10-18)
Since its discovery, the unique properties of the naturally occurring amino acid, L-ergothioneine (EGT; 2-mercaptohistidine trimethylbetaine), have intrigued researchers for more than a century. This widely distributed thione is only known to be synthesized by non-yeast fungi, mycobacteria and cyanobacteria
C Sao Emani et al.
Journal of biomedical science, 25(1), 55-55 (2018-07-13)
Three low molecular weight thiols are synthesized by Mycobacterium tuberculosis (M.tb), namely ergothioneine (ERG), mycothiol (MSH) and gamma-glutamylcysteine (GGC). They are able to counteract reactive oxygen species (ROS) and/or reactive nitrogen species (RNS). In addition, the production of ERG is
Kei Obayashi et al.
Journal of cosmetic science, 56(1), 17-27 (2005-03-04)
Ergothioneine (EGT) is a sulfur-containing amino acid, and is presumed to function as a natural antioxidant. The purpose of this study was to identify the nature of the antioxidant activity and investigate the effects of EGT on UV-induced cellular response.
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