L-(+)-Ergothioneine (EGT) is a natural chiral amino-acid antioxidant biosynthesized in certain bacteria and fungi. It is an important bioactive compound which has been used as a radical scavenger, an ultraviolet ray filter, a regulator of oxidation-reduction reactions and cellular bioenergetics, and a physiological cytoprotector, etc.
|Chemical name||(α-S)-α-Carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt|
|Melting Point||255-259° C|
|Half Life||around 30 days|
|Solubility||Soluble in water (50 mg/ml), acetone, hot ethanol, and methanol.|
|Storage Condition||-20°C (des.)|
|Application||An antioxidant and free radical scavenger|
L-Ergothioneine is a stable antioxidant that can be found under conditions of excessive oxidative stress in plant and animal tissue. L-ergothioneine has the ability to scavenge free radicals and protect cells from UV-induced ROS with higher efficiency than antioxidants coenzyme Q(10) or idebenone, thus making it more effective antioxidant. The compound has been shown to be a non-toxic thiol buffering antioxidant, enhance cell viability induced by hydrogen peroxide (H2O2), and inhibit DNA oxidation by peroxynitrite (ONOO-) in the human neuronal hybridoma cell line (N-18-RE-105).
EGT is made in relatively few organisms, notably Actinobacteria, Cyanobacteria, and certain fungi. Ergothioneine was discovered in 1909 and named after the ergot fungus from which it was first purified, with its structure being determined in 1911.
l-(+) Ergothioneine is a naturally occurring thiol amino acid with antioxidant properties and potential benefits as a dietary supplement. Despite its century-old identification and wide distribution in human food, little is known of its mechanism of action and safety.
L-(+)-Ergothioneine has been used:
L-Ergothioneine–a new type of natural antioxidant
EGT is a natural chiral amino-acid antioxidant biosynthesized in certain bacteria and fungi. It is an important bioactive compound which has been used as a radical scavenger, an ultraviolet ray filter, a regulator of oxidation-reduction reactions and cellular bioenergetics, and a physiological cytoprotector, etc.
L-Ergothioneine( EGT, ERGO, CAS: 497-30-3), also known as (S)-α-Carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt, was initially extracted from ergot by Tanret C in 1909, then it was also discovered in animal blood. Pure EGT is white crystal, soluble in water, (dissolved 0.9mol/L at room temperature). Autoxidation cannot occur at physiological pH value or in strong alkaline solution. EGT can exist in two isomer forms — a thiol form and a thione form, as shown below:
With advantages of multi-functions, EGT stands out among many other antioxidants.Advantages (compared with glutathione, cysteine etc.):
——EGT is easier to accumulate in cells and the concentration is more stable than other antioxidants.
——EGT is more effective on reducing cell death caused by pyrogallol.
——EGT mainly scavenges ROS to prevent oxidation, while glutathione and others scavenge free radicals, that is, other antioxidants scavenge oxidation products.
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), for the incubation of experimental cells while performing in vitro kinase activity assays for ATM (Ataxia telangiectasia mutated) or ATR (ATM- and RAD3-related).
COMPARISON OF ANTIOXIDATION
Results: EGT was the most active scavenger of free radicals as compared to classic antioxidants as GSH, uric acid and trolox. In particular, the highest antioxidant capacity exhibited by EGT vs. peroxyl radicals resulted 25% higher than the value obtained with the reference antioxidant trolox. The scavenging capacity of EGT towards hydroxyl radicals was 60% higher, as compared to uric acid,which represent the reference antioxidant vs. hydroxyl radicals. Finally, EGT showed the highest antioxidant activity also towards peroxynitrite, with a scavenging capacity 10% higher than that of uric acid.
EGT also has effects on regulating intracellular energy,
improving the survival rate of sperm,
protecting the liver from injury,
developmental defects and cataract.
5-10mg per unit for an adult and 2-3 units continuous intake is essential in your daily diet.
Source: Li Yiqun, Zhou Nianbo. Biology Functions and Applications of EGT [J]. Food Engineering，2010，9（3）：26-28.
■ Intakes are listed as follows:
Data source: Tetrahedron when applying for US NDI
■Data suggest: 10.5mg/g for OXIS’s ADI (Acceptable Daily Intake).