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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The effect of turmeric (Curcuma longa) extract on the functionality of the solute carrier protein 22 A4 (SLC22A4) and interleukin-10 (IL-10) variants associated with inflammatory bowel disease
McCann M, et al.
Nutrients, 6(10), 4178-4190 (2014)
Marco H Bello et al.
Fungal genetics and biology : FG & B, 49(2), 160-172 (2012-01-03)
Ergothioneine (EGT) is a histidine derivative with sulfur on the imidazole ring and a trimethylated amine; it is postulated to have an antioxidant function. Although EGT apparently is only produced by fungi and some prokaryotes, it is acquired by animals
Akshamal M Gamage et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, fj201800716-fj201800716 (2018-06-12)
Bacteria use various endogenous antioxidants for protection against oxidative stress associated with environmental survival or host infection. Although glutathione (GSH) is the most abundant and widely used antioxidant in Proteobacteria, ergothioneine (EGT) is another microbial antioxidant, mainly produced by fungi
Irwin K Cheah et al.
Antioxidants (Basel, Switzerland), 9(7) (2020-07-11)
Infection with SARS-CoV-2 causes the coronavirus infectious disease 2019 (COVID-19), a pandemic that has, at present, infected more than 11 million people globally. Some COVID-19 patients develop a severe and critical illness, spurred on by excessive inflammation that can lead
B D Paul et al.
Cell death and differentiation, 17(7), 1134-1140 (2009-11-17)
Ergothioneine (ET) is an unusual sulfur-containing derivative of the amino acid, histidine, which is derived exclusively through the diet. Although ET was isolated a century ago, its physiologic function has not been clearly established. Recently, a highly specific transporter for
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