Page last updated: 2024-12-10

ergothioneine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Occurs in Manufacturing Related Drugs Related Conditions Protein Interactions Research Growth

Description

ergothioneine thione form : A L-histidine derivative that is N(alpha),N(alpha),N(alpha)-trimethyl-L-histidine in which the hydrogen at position 2 on the imdazole ring is replaced by a thioxo group. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID5351619
CHEMBL ID5209630
CHEBI ID4828
CHEBI ID82707
SCHEMBL ID188140
SCHEMBL ID9985141
MeSH IDM0007666

Synonyms (57)

Synonym
unii-bdz3dqm98w
bdz3dqm98w ,
1h-imidazole-4-ethanaminium, alpha-carboxy-2,3-dihydro-n,n,n-trimethyl-2-thioxo-, inner salt, (alphas)-
AB01275464-01
sympectothion
thiolhistidine-betaine
l-thioneine
l-ergothioneine ,
497-30-3
ergothioneine ,
l-(+)-ergothioneine
ergothionine
(s)-(1-carboxy-2-(2-mercaptoimidazol-4-yl)ethyl)trimethylammonium hydroxide
1h-imidazole-4-ethaniminium, alpha-carboxy-2,3-dihydro-n,n,n-trimethyl-2-thioxo-, hydroxide, inner salt, (s)-
ai3-23492
einecs 207-843-5
nsc 7175
1h-imidazole-4-ethanaminium, alpha-carboxy-2,3-dihydro-n,n,n-trimethyl-2-thioxo-, inner salt, (s)-
1h-imidazole-4-ethanaminium, alpha-carboxy-2,3-dihydro-n,n,n-trimethyl-2-thioxo-, hydroxide, inner salt, (s)-
ammonium, (1-carboxy-2-(2-mercaptoimidazol-4-yl)ethyl)trimethyl-, hydroxide, inner salt, l-(+)-
HMS2089D04
(alphas)-alpha-carboxy-2,3-dihydro-n,n,n-trimethyl-2-thioxo-1h-imidazole-4-ethanaminium inner salt
(2s)-3-(2-mercapto-1h-imidazol-5-yl)-2-(trimethylammonio)propanoate
2-mercaptohistidine trimethylbetaine
erythrothioneine
thiolhistidinebetaine
ergothioneine thiol
CHEBI:4828
(2s)-3-(2-mercapto-1h-imidazol-5-yl)-2-(trimethylazaniumyl)propanoate
3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoate
(2s)-3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-(trimethylazaniumyl)propanoate
ergothioneine [inci]
(.alpha.s)-.alpha.-carboxy-2,3-dihydro-n,n,n-trimethyl-2-thioxo-1h-imidazole-4-ethanaminium inner salt
ergothioneine [mi]
1h-imidazole-4-ethanaminium, .alpha.-carboxy-2,3-dihydro-n,n,n-trimethyl-2-thioxo-, inner salt, (.alpha.s)-
CCG-207908
SCHEMBL188140
ergothioneine thione form
ergothioneine thione
CHEBI:82707
(2s)-3-(2-thioxo-2,3-dihydro-1h-imidazol-4-yl)-2-(trimethylazaniumyl)propanoate
nalpha,nalpha,nalpha-trimethyl-2-sulfanylidene-2,3-dihydro-l-histidine
ergothioneine (thione form)
SCHEMBL9985141
mfcd00167474
(2s)-3-(2-sulfanylidene-2,3-dihydro-1h-imidazol-4-yl)-2-(trimethylazaniumyl)propanoate
AKOS027325505
(s)-3-(2-thioxo-2,3-dihydro-1h-imidazol-4-yl)-2-(trimethylammonio)propanoate
CS-0018211
HY-N1914
Q614788
DTXSID901020082
D83035
ergothionine;l-(+)-ergothioneine;erythrothioneine
ergothioneine l-(+)
A930109
CHEMBL5209630

Research Excerpts

Toxicity

L-Ergothioneine was well tolerated and without adverse effects on the reproductive parameters evaluated. No adverse clinical, body weight/gain, food consumption and efficiency, clinical pathology, or histopathological changes associated with the administration of the nature-identical ergothsioneine were observed.

ExcerptReferenceRelevance
" In conclusion, L-Ergothioneine was well tolerated and without adverse effects on the reproductive parameters evaluated."( Reproductive safety evaluation of L-Ergothioneine.
Erdelmeier, I; Forster, R; Moutet, M; Papineau, D; Sabadie, C; Spézia, F; Yadan, JC, 2015
)
0.42
" Following a preliminary 28-day study, a repeated dose 90-day gavage study at dose levels of 0, 400, 800, and 1,600 mg/kg body weight (bw)/d in Sprague Dawley rats, in which dose-proportional systemic absorption was confirmed by plasma analysis, no adverse clinical, body weight/gain, food consumption and efficiency, clinical pathology, or histopathological changes associated with the administration of the nature-identical ergothioneine were observed."( A Safety Evaluation of a Nature-Identical l-Ergothioneine in Sprague Dawley Rats.
Marone, PA; Trampota, J; Weisman, S, 2016
)
0.43
" Equally important, ergothioneine inhibited γ-glutamyl transpeptidase that plays crucial roles in biotransformation of cisplatin into a toxic metabolite."( Ergothioneine mitigates cisplatin-evoked nephrotoxicity via targeting Nrf2, NF-κB, and apoptotic signaling and inhibiting γ-glutamyl transpeptidase.
Abd-Allah, GM; Elshafey, MM; Gad, HS; Mohamadin, AM; Salama, SA, 2021
)
0.62

Pharmacokinetics

ExcerptReferenceRelevance
"These data suggest that diet-drug pharmacokinetic interactions may occur during co-exposure to gabapentin and mushroom constituents."( Effect of mushroom diet on pharmacokinetics of gabapentin in healthy Chinese subjects.
Goh, BC; Lee, EJ; Limenta, LM; Murray, M; Toh, DS; Wang, LZ; Yee, JY, 2014
)
0.4

Compound-Compound Interactions

ExcerptReferenceRelevance
" Therefore, the present study investigated the protective effect of L-egt alone, or combined with metformin, on renal damage in a type-2 diabetic (T2D) rat model."( L-ergothioneine and its combination with metformin attenuates renal dysfunction in type-2 diabetic rat model by activating Nrf2 antioxidant pathway.
Channa, ML; Dare, A; Nadar, A, 2021
)
0.62

Bioavailability

ExcerptReferenceRelevance
" The bioavailability of ET from mushrooms in humans remains unclear."( The bioavailability of ergothioneine from mushrooms (Agaricus bisporus) and the acute effects on antioxidant capacity and biomarkers of inflammation.
Beelman, RB; Kris-Etherton, PM; Weigand-Heller, AJ, 2012
)
0.38
"We evaluated the bioavailability of ET in healthy men (n=10) in a pilot study, using a randomized, cross-over, dose-response, postprandial time-course design, conducted at the General Clinical Research Center at Pennsylvania State University in 2009."( The bioavailability of ergothioneine from mushrooms (Agaricus bisporus) and the acute effects on antioxidant capacity and biomarkers of inflammation.
Beelman, RB; Kris-Etherton, PM; Weigand-Heller, AJ, 2012
)
0.38
" Dietary supplementation with extracts from mushroom processing waste significantly improved ERG bioavailability in the blood of yellowtail fish and muscle tissue of cattle."( A rapid HPLC post-column reaction analysis for the quantification of ergothioneine in edible mushrooms and in animals fed a diet supplemented with extracts from the processing waste of cultivated mushrooms.
Giri, A; Nguyen, TH; Ohshima, T, 2012
)
0.38
" Retrospectively, we studied 37 subjects who had participated in a dietary intervention focused on vitamin D bioavailability from white button mushrooms (WBM)."( A Retrospective Study in Adults with Metabolic Syndrome: Diabetic Risk Factor Response to Daily Consumption of Agaricus bisporus (White Button Mushrooms).
Beelman, RB; Cai, W; Calvo, MS; Goh, BC; Kalaras, MD; Mehrotra, A; Nadkarni, G; Uribarri, J; Wang, L, 2016
)
0.43
"Ergothioneine (ERGO) is a potent antioxidant and anti-inflammatory amino acid that is highly bioavailable to humans from the diet."( Health consequences of improving the content of ergothioneine in the food supply.
Ba, DM; Beelman, RB; Duiker, SW; Kalaras, MD; Phillips, AT; Richie, JP, 2022
)
0.72

Dosage Studied

ExcerptRelevanceReference
" Ergothioneine, independently from the dosage used, failed to: (i) increase recovery of developed pressure upon reperfusion (14."( In vitro administration of ergothioneine failed to protect isolated ischaemic and reperfused rabbit heart.
Bernocchi, P; Cargnoni, A; Ceconi, C; Curello, S; Ferrari, R, 1995
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Occurs in Manufacturing (2 Product(s))

Product Categories

Product CategoryProducts
Beauty & Personal Care2

Products

ProductBrandCategoryCompounds Matched from IngredientsDate Retrieved
MyChelle Dermaceuticals Brighten Perfect C Cleansing Oil -- 4.2 fl ozMyChelle DermaceuticalsBeauty & Personal Careascorbic acid, ergothioneine, sodium lauroyl sarcosinate, sodium bicarbonate2024-11-29 10:47:42
MyChelle Dermaceuticals Protect Replenishing Solar Defense Sunscreen SPF 30 -- 2.3 fl ozMyChelle DermaceuticalsBeauty & Personal Cared-alpha, citric acid, cetearyl alcohol, citric acid, tocopherol, behenyl alcohol, ergothioneine, tocopherol, glyceryl stearate, glycerin, malic acid, phytic acid, sodium lactate2024-11-29 10:47:42

Roles (5)

RoleDescription
antioxidantA substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
fungal metaboliteAny eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
xenobiotic metaboliteAny metabolite produced by metabolism of a xenobiotic compound.
chelatorA ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.
fungal metaboliteAny eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
xenobiotic metaboliteAny metabolite produced by metabolism of a xenobiotic compound.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (4)

ClassDescription
amino-acid betaineAny amino acid-derived zwitterion - such as glycine betaine (N,N,N-trimethylammonioacetate) - in which the ammonium nitrogen carries methyl substituents and bears no hydrogen atoms.
L-histidine derivativeA proteinogenic amino acid derivative resulting from the formal reaction of L-histidine at the amino group, carboxy group, or the imidazolyl moiety, or from the replacement of any hydrogen of L-histidine by a heteroatom.
sulfur-containing amino acid
amino-acid betaineAny amino acid-derived zwitterion - such as glycine betaine (N,N,N-trimethylammonioacetate) - in which the ammonium nitrogen carries methyl substituents and bears no hydrogen atoms.
L-histidine derivativeA proteinogenic amino acid derivative resulting from the formal reaction of L-histidine at the amino group, carboxy group, or the imidazolyl moiety, or from the replacement of any hydrogen of L-histidine by a heteroatom.
1,3-dihydroimidazole-2-thionesA member of the class of imidazoles that is 1,3-dihydroimidazole-2-thione and its derivatives by substitution.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (7)

PathwayProteinsCompounds
Transport of small molecules39295
SLC-mediated transmembrane transport13567
Transport of bile salts and organic acids, metal ions and amine compounds4928
Organic cation/anion/zwitterion transport67
Organic cation transport54
ergothioneine biosynthesis I (bacteria)522
ergothioneine biosynthesis II (fungi)215

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Solute carrier family 22 member 4Homo sapiens (human)IC50 (µMol)40.000040.000040.000040.0000AID1794816
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (10)

Processvia Protein(s)Taxonomy
carnitine transportSolute carrier family 22 member 4Homo sapiens (human)
triglyceride metabolic processSolute carrier family 22 member 4Homo sapiens (human)
sodium ion transportSolute carrier family 22 member 4Homo sapiens (human)
neurotransmitter transportSolute carrier family 22 member 4Homo sapiens (human)
carnitine metabolic processSolute carrier family 22 member 4Homo sapiens (human)
quaternary ammonium group transportSolute carrier family 22 member 4Homo sapiens (human)
xenobiotic transportSolute carrier family 22 member 4Homo sapiens (human)
amino acid import across plasma membraneSolute carrier family 22 member 4Homo sapiens (human)
acetate ester transportSolute carrier family 22 member 4Homo sapiens (human)
carnitine transmembrane transportSolute carrier family 22 member 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
acetylcholine transmembrane transporter activitySolute carrier family 22 member 4Homo sapiens (human)
protein bindingSolute carrier family 22 member 4Homo sapiens (human)
ATP bindingSolute carrier family 22 member 4Homo sapiens (human)
secondary active organic cation transmembrane transporter activitySolute carrier family 22 member 4Homo sapiens (human)
amino acid transmembrane transporter activitySolute carrier family 22 member 4Homo sapiens (human)
amino-acid betaine transmembrane transporter activitySolute carrier family 22 member 4Homo sapiens (human)
carnitine transmembrane transporter activitySolute carrier family 22 member 4Homo sapiens (human)
symporter activitySolute carrier family 22 member 4Homo sapiens (human)
quaternary ammonium group transmembrane transporter activitySolute carrier family 22 member 4Homo sapiens (human)
PDZ domain bindingSolute carrier family 22 member 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
mitochondrionSolute carrier family 22 member 4Homo sapiens (human)
plasma membraneSolute carrier family 22 member 4Homo sapiens (human)
basal plasma membraneSolute carrier family 22 member 4Homo sapiens (human)
apical plasma membraneSolute carrier family 22 member 4Homo sapiens (human)
mitochondrial membraneSolute carrier family 22 member 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Research

Studies (511)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990180 (35.23)18.7374
1990's23 (4.50)18.2507
2000's51 (9.98)29.6817
2010's154 (30.14)24.3611
2020's103 (20.16)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (0.96%)5.53%
Reviews46 (8.85%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other469 (90.19%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (4)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Investigating the Efficacy of Ergothioneine to Delay Cognitive Decline in Mild Cognitively Impaired Subjects [NCT03641404]Phase 3106 participants (Anticipated)Interventional2018-08-31Not yet recruiting
A Pilot Study of Dietary Taxifolin/Dihydroquercetin and Ergothioneine and Immune Biomarkers in Healthy Volunteers [NCT05190432]90 participants (Actual)Interventional2021-11-10Active, not recruiting
Clinical Study on Rapid Antioxidant Protection and Immune Modulating Effects. [NCT05042674]24 participants (Anticipated)Interventional2021-09-20Recruiting
A Placebo-controlled, Randomized, Double-blind Trial to Assess the Effects of Ergothioneine on Cognition, Mood, and Sleep in Healthy Adult Men and Women [NCT04556032]4 participants (Actual)Interventional2020-09-09Terminated(stopped due to Sponsor terminated study due to unforeseen recruitment circumstances amidst the COVID19 pandemic.)
[information is prepared from clinicaltrials.gov, extracted Sep-2024]