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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H15N3O2S
Molecular Weight 229.299
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ERGOTHIONEINE

SMILES

C[N+](C)(C)[C@@H](CC1=CNC(=S)N1)C([O-])=O

InChI

InChIKey=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

HIDE SMILES / InChI

Description

ERGO (Ergothioneine) is naturally occurring antioxidant derived from the diet and abundantly contained in golden oyster mushroom (Pleurotus cornucopiae var. citrinopileatus. It is hydrophilic and membrane impermeable, but is well absorbed from the gastrointestinal tract due to the presence of a specific carrier‐mediated transport system, carnitine/organic cation transporter OCTN1/SLC22A4, essential for the beta-oxidation of fatty acids. Numerous in vitro assays have demonstrated the antioxidant and cytoprotective capabilities of ERGO against a wide range of cellular stressors, but an antioxidant role has yet to be fully verified in vivo. Nevertheless, the accumulation, tissue distribution, and scavenging properties, all highlight the potential for EGT to function as a physiological antioxidant. Because ERGO is highly distributed into the brain after oral ingestion, OCTN1 may contribute to the alleviation of oxidative stress and promotion of neuronal differentiation via the uptake of ERGO in the brain, perhaps abating symptoms of neurological disorders.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
in mice: To clarify the exposure of ERGO (ergothioneine) to brain and the possible antidepressant‐like effect after oral ingestion, ERGO or GOME (golden oyster mushroom extract) which contains 1.2% (w/w) ERGO was mixed with feed and provided to mice for 2 weeks, and then ERGO concentration and antidepressant‐like effect were evaluated by LC‐MS/MS and FST (forced swimming test) or TST (tail suspension test), respectively.
Route of Administration: Oral
In Vitro Use Guide
Human OCTN1 was expressed in 293 cells. Analysis of transport efficiency of stachydrine-related solutes, affinity, and Na+ dependence indicates that the physiological substrate is ergothioneine (ET). Efficiency of transport of ET was as high as 195 μl per min per mg of protein. By contrast, the carnitine transporter OCTN2 from rat did not transport ET at all