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L-(+)-Ergothioneine
Ergothionein is a natural antioxidant that can protect cells in the human body and is an important active substance in the body. Natural antioxidants are safe, non-toxic, and have become a hot research topic. As a natural antioxidant, ergothionein has entered people's field of vision. It has various physiological functions such as clearing free radicals, detoxification, maintaining DNA biosynthesis, normal cell growth, and cellular immunity.
Antioxidant effect
Ergothionein is a natural amino acid derived from plants and can accumulate in animals. Studies have shown that it has antioxidant properties. It can effectively clear - OH, chelate divalent iron and copper ions, prevent H2O2 from generating - OH under the action of iron or copper ions, and inhibit the oxidation of copper dependent oxygenated hemoglobin. It can also inhibit the peroxidation reaction of arachidonic acid that occurs when myoglobin (or hemoglobin) is mixed with H2O2. Ergothionein can also strongly scavenge hypochlorous acid, thereby preventing the inactivation of A1- antiprotease. However, it cannot inhibit the peroxidation reaction of lipid particles in the presence of iron ions. AKanmu D et al. found that a certain concentration of ergothionein can act as an antioxidant in the body.
Protective effect on cells
Ergothionein is a powerful hypochlorous acid scavenger (HOCl), and although many compounds can react with hypochlorous acid, few can react as rapidly as ergothionein. A1- Anti protease inhibitors (APIs), such as elastase, are particularly sensitive to hypochlorous acid, and physiological concentrations of ergotamine can effectively protect APIs against inactivation caused by hypochlorous acid. As neutrophils are the main source of hypochlorous acid in the body, one of the functions of ergotamine is to protect red blood cells from harm from neutrophils in normal functioning or pathological inflammatory sites.
anti-inflammatory effect
Peroxynitrite is the endogenous formation of the limited diffusion reaction of NO and superoxide, and is a strong oxidant related to the pathophysiology of inflammation, such as ischemia reperfusion injury, atherosclerosis, acute pneumonia and sepsis. Ergothionein can inhibit amino acid oxidation mediated by peroxynitrite anions, such as tyrosine nitration, thus providing feasibility for the treatment of inflammation.
Other biological functions
Since the discovery of ergothionein, many people have attempted to explain its physiological functions, but none have been able to fully define its physiological functions. Brummel. m.c's research found that ergothionein may also have the following functions: catalytic action for transporting cations and carbon dioxide carboxylation or decarboxylation reactions; Regulating thyroid and anti thyroid effects; Regulating histamine or antihistamine effects; Choline like function or anti parasympathetic neurophysiological effects; It can regulate the reaction activity of other acyl carriers or act as an acid based carrier itself. Epand R M et al also studied the effect of ergotin on diabetes.
It has strong antioxidant activity: clearing reactive oxygen species, chelating divalent metal ions, activating antioxidant enzymes, inhibiting superoxide dismutase, and inhibiting oxidation reactions of various heme proteins. Due to these characteristics of ergothionein, it has a wide range of applications and market prospects in fields such as medicine, food and beverage, functional foods, animal feed, cosmetics, and biotechnology.
the new supersedes the old
Studies have shown that ergothionein cannot be synthesized in animal bodies, but it has been clearly demonstrated in plants and microorganisms that histidine, the sulforam, and the methyl groups of methionine can be incorporated into ergothionein. D. Yanasugondha and M D. Appleman studied the catabolism of ergothionein in microorganisms and found that ergothionein can be converted into trimethylamine and mercaptan imidazolium acrylic acid; Heath [3] found that ergothionein labeled with [S] was distributed in the bone marrow, red blood cells, liver, kidneys, and other parts of rats after feeding them with food containing [S] ergothionein for 21 days. George Wolf et al. first injected [α - S] ergotamine into mice, and then studied the distribution of radioactive energy and its metabolites. It has been proven that herzynine is a precursor for the synthesis of ergothionein.
| L-(+)-Ergothioneine Basic information |
| Product Name: | L-(+)-Ergothioneine |
| Synonyms: | L-(+)-ERGOTHIONEINE INNER SALT;ERGOLD;2-MERCAPTOHISTIDINE BETAINE;(S)-ALPHA-CARBOXY-2,3-DIHYDRO-N,N,N-TRIMETHYL-2-THIOXO-1H-IMIDAZOLE-4-ETHANAMINIUM INNER SALT;THIONEINE;(S)-[1-carboxy-2-(2-mercaptoimidazol-4-yl)ethyl]trimethylammonium hydroxide;1H-Imidazole-4-ethanaminium, .alpha.-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-, inner salt, (.alpha.S)-;3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoate |
| CAS: | 497-30-3 |
| MF: | C9H15N3O2S |
| MW: | 229.3 |
| EINECS: | 207-843-5 |
| Product Categories: | Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;cosmetics |
| Mol File: | 497-30-3.mol |
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| L-(+)-Ergothioneine Chemical Properties |
| Melting point | 275-277°C (dec.) |
| density | 1.2541 (rough estimate) |
| refractive index | 1.6740 (estimate) |
| storage temp. | -20°C |
| solubility | Soluble in Water (up to 10 mg/ml) |
| form | White solid. |
| color | White or off-white |
| PH | +47^o (c=1 in water) |
| Stability: | Stable for 1 year from date of purchase as supplied. Solutions in water may be stored at -20°C for no more then 1 day. |
| InChI | InChI=1/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-/s3 |
| InChIKey | SSISHJJTAXXQAX-KPOCXSGKNA-N |
| SMILES | [N+](C)(C)(C)[C@@H](CC1=CNC(S)=N1)C([O-])=O |&1:4,r| |
| EPA Substance Registry System | 1H-Imidazole-4-ethanaminium, .alpha.-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-, inner salt, (.alpha.S)- (497-30-3) |
| Safety Information |
| WGK Germany | 3 |
| HS Code | 2933299090 |
| MSDS Information |
| Provider | Language |
|---|---|
| SigmaAldrich | English |
| L-(+)-Ergothioneine Usage And Synthesis |
| Description | L-(+)-Ergothioneine is a naturally-occurring amino acid derived from histidine via hercynine. Ergothioneine is a stable antioxidant that scavenges and detoxifies free radicals and oxidants, increases intracellular thiol levels, controls nuclear factor-κB activation, and inhibits inflammatory gene expression. In addition, it inhibits the peroxynitrite-dependent nitration of nitrotyrosine, blocks oxidative DNA damage and cell death, and prevents the formation of xanthine and hypoxanthine. Ergothioneine is transported by the organic cation/carnitine transporter 1, which has been linked with autoimmune diseases, including rheumatoid arthritis and Crohn’s disease. |
| Chemical Properties | White Solid |
| Uses | L-(+)-Ergothioneine is a natural molecule isolated from the rye ergot fungus and later identified in rat erythrocytes and liver and in numerous other animal tissues. Its antioxidizing properties may afford the compound therapeutic potential or it may be used as a food additive or in cosmetics. |
| Definition | ChEBI: Ergothioneine is 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 mercapto group. A naturally occurring metabolite of histidine synthesized by bacteria and fungi with antioxidant properties. It is found ubiquitously in plants and animals and is present in many human foodstuffs. It has a role as an antioxidant, a fungal metabolite, a plant metabolite, a xenobiotic metabolite and a chelator. It is an amino-acid betaine, a L-histidine derivative and a sulfur-containing amino acid. It is a conjugate base of an ergothioneine(1+). It is a tautomer of an ergothioneine thione form. |
| Origin | Ergothioneine was discovered in 1909 by Charles Tanret, a French pharmacist and chemist. Tanret was examining the ergot fungus, which had recently been responsible for destroying crops, and he discovered the compound by using a purification process. The amino acid name ergothioneine originates from this fungus. Though this discovery is relatively recent, scientists speculate that ergothioneine may have originated from ancient earth. Due to its anaerobic nature (it does not require oxygen to function), it may have manifested in the earth's oxygen-free atmosphere more than three billion years ago While ergothioneine is not classified as one of the nine essential amino acids. |
| benefits | L-(+)-Ergothioneine is a natural antioxidant, which has various physiological functions such as scavenging free radicals, detoxification, maintaining DNA biosynthesis, normal cell growth and cellular immunity. |
| General Description | L-(+)-Ergothioneine (ERG) is a substance that cannot be synthesized by humans and must be obtained from food. It has cytoprotective and antioxidant properties. |
| 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. |
| 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. |
| Synthesis | The synthesis of L-(+)-Ergothioneine (ET; marketed as Ergoneine®) is performed in water and includes the following steps. First, l-hercynine is reacted with bromine and then with cysteine. The intermediate obtained is transformed into ET by heating in the presence of mercaptopropionic acid. Finally, the raw product is purified by crystallisation. |
| Synthesis | L-(+)-Ergothioneine is prepared by the reaction of hercynine. The steps are as follows: 15g of compound was added to 150ml of water, and 15.6g of concentrated hydrochloric acid was added, add 10.9g dibromohydantoin, stir for 20min, add D-cysteine, Continue to stir for 1 hour, add sodium thiosulfate, raise the temperature to 90-100°C, and continue the reaction for 15 hours. After the reaction, cool down and filter, adjust the pH to neutral, desalt, concentrate, crystallize with 5ml of water and 75ml of isopropanol, and dissolve the solid Filter and dry at 70-80°C to obtain 88% ergothioneine product with a yield of 81%.  |
| References | [1] Williamson R, et al. L-(+)-Ergothioneine Significantly Improves the Clinical Characteristics of Preeclampsia in the Reduced Uterine Perfusion Pressure Rat Model. Hypertension , 2022; 75. [2] Hoek S, et al. Engineering the Yeast Saccharomyces cerevisiae for the Production of L-(+)-Ergothioneine. Frontiers in Bioengineering and Biotechnology, 2019. |
Application areas of ergothionein
1. Pharmaceutical field
The application prospects of ergothionein in the pharmaceutical field are broad. As a natural antioxidant, it can be used to prevent and treat various diseases related to oxidative stress, such as cardiovascular disease, cancer, neurodegenerative diseases, etc. In addition, ergotamine also has insecticidal, skin disease treatment, and neuropathic headache relief effects. Its insecticidal effect is mainly reflected in the destruction of the parasite's neural transmission system, leading to paralysis and death of the parasite; In the treatment of skin diseases, the antifungal and anti-inflammatory effects of ergotamine can reduce the scope of infection, alleviate itching and inflammation; In the treatment of neuropathic headaches, it relieves pain by constricting blood vessels and inhibiting the release of serotonin.
2. Health products and food industry
With the improvement of health awareness, health products and foods rich in ergotamine are increasingly favored by consumers. As a safe and non-toxic natural antioxidant, ergotamine is widely used in various health products and functional foods. It not only provides antioxidant protection, but also enhances immunity and delays aging. In the field of food processing, ergotamine is also used as an antioxidant to extend the shelf life of food and maintain its nutritional value.
3. Cosmetics field
The application of ergotamine in the field of cosmetics is becoming increasingly widespread. Due to its effective resistance to free radical damage, ergotamine is added to various skincare products to delay the aging process of the skin. It can protect skin cells from external factors such as ultraviolet radiation, reduce the formation of wrinkles and pigmentation, and keep the skin youthful.
