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E7521

Sigma-Aldrich

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
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.32

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

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

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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

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:
  • 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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Natural amino acid found in the fungus Claviceps purpurea

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ling-Zhi Wang et al.
Journal of mass spectrometry : JMS, 48(3), 406-412 (2013-03-16)
A sensitive analytical method has been developed and validated for the quantification of L-ergothioneine in human plasma and erythrocytes by liquid chromatography-tandem mass spectrometry. A commercially available isotope-labeled L-ergothioneine-d9 is used as the internal standard. A simple protein precipitation with
L-Ergothioneine improves the developmental potential of in vitro sheep embryos without influencing OCTN1-mediated cross-membrane transcript expression
Mishra A, et al.
Zygote, 26(2), 149-161 (2018)
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
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

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