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L-Ergocryptine's Effects and Multi-industry Applications

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SeeBio's L-Ergothioneine(EGT, CAS: 497-30-3) is a rare chiral amino acid that has multiple cellular physiological protective functions, including clearing free radicals, detoxification, maintaining DNA biosynthesis, promoting normal cell growth, enhancing the cellular immune system, providing anti-radiation, skin-whitening and anti-aging properties. Due to its excellent performance, it can be applied in many fields. In the cosmetics field, it can be used for anti-aging and made into sunscreen products. In the pharmaceutical field, it can be used to treat inflammation and made into tablets, capsules, oral preparations, etc. In the health supplement field, it can prevent cancer occurrence and be made into functional foods, functional beverages, etc. It has been included in the EU's novel food resource list.
EGT is a rare natural chiral amino acid (a sulfur-containing histidine derivative) with the following chemical structure:
EGT is a compound discovered in 1909 that was detected in the fungus Claviceps purpurea. The pure compound is a white crystalline solid, exhibiting water solubility (soluble up to 0.9mol/L at room temperature). Under physiological pH conditions and in strongly alkaline solutions, EGT does not auto-oxidize. In its dissolved state, there exists an enolic-thiol tautomerism between the thiolone and thiol forms.
Isomerism of Thione and Thiol in L-Ergothioneine
Efficacy of L-Ergothioneine
Powerful Antioxidant:L-Ergothioneine has long been recognized as a potent low-molecular-weight antioxidant. It enters the human body mainly through dietary intake and can accumulate in cells under conditions of high oxidative stress. Compared to other antioxidants like resveratrol, L-Ergothioneine has higher bioavailability. This is because L-Ergothioneine possesses unique biological characteristics, allowing it to accumulate through the OCTN1 transporter (L-Ergothioneine transporter) in skin cells and tissues. In contrast to most water-soluble antioxidants, L-Ergothioneine cannot penetrate cell membranes but is transported through cells via OCTN1. The antioxidant effects of L-Ergothioneine in the body include direct scavenging of reactive oxygen species, chelation of various divalent metal cations, activation of antioxidant enzymes (such as glutathione reductase and mitochondrial superoxide dismutase), and inhibition of oxidation of hemoglobin (such as hemin and myoglobin).
Inhibition of UV-induced damage and cell apoptosis: UV radiation activates various growth factor and cell factor receptor-related signaling pathways, leading to damage to DNA, proteins, lipids, and cell apoptosis. L-Ergothioneine has the ability to inhibit the expression of genes induced by UV, such as MMP-1 (mainly degrading type I collagen) and TNF-α (promoting the production of inflammatory factors), thereby reducing the occurrence of these damages. It also possesses anti-photoaging abilities, effectively inhibiting the process of UV-induced DNA, protein, and lipid damage, as well as cell apoptosis.
Protective effects on cells: Ergothioneine can also effectively clear perchlorate and thus prevent inactivation of alpha-1 antitrypsin. Ergothioneine exerts antioxidant effects at certain concentrations in vivo, effectively protecting cells from oxidative damage. Its ability to clear perchlorate makes it a powerful protector, especially for perchlorate-sensitive enzymes like alpha-1 antitrypsin. Ergothioneine can effectively protect them from perchlorate-induced inactivation. Since neutrophils are the main source of perchlorate in the body, one of ergothioneine's roles is to protect red blood cells from damage by neutrophils from normal function or pathogenic inflammatory sites.
Anti-inflammatory effects:Ergothioneine can inhibit peroxynitrite anion-mediated amino acid oxidation, such as nitration of tryptophan, providing feasibility for treating inflammation-associated pathophysiology. In addition, ergothioneine may have various biological functions, including transporting cations and catalyzing carboxylation or decarboxylation reactions, regulating thyroid and anti-thyroid effects, regulating histaminergic or antihistaminergic effects, cholinergic functions or parasympathetic physiological effects, thereby providing feasibility for treating inflammation.
Product CAS NO. Grade Packing
L-Ergothioneine 497-30-3 Cosmetic Grade,98% 100g,1kg, 5kg,25kg
L-Ergothioneine 497-30-3 Food grade, 98% 100g,1kg, 5kg,25kg
For more product details, please contact us: service@seebio.cn or Phone: +86 21 58183719 or Wechat: +86 158 0195 7578
Application in the Cosmetic Industry
L-Ergothioneine is widely used in cosmetics as an antioxidant, especially in skincare products. It effectively reduces oxidative stress by eliminating free radicals, decreasing skin damage, and signs of aging caused by ultraviolet radiation. EGT enhances the resistance of skin cells, reduces damage to DNA, proteins, and lipids, facilitates DNA repair, increases cell survival rates, and promotes skin health. As a natural antioxidant ingredient, the application of EGT in cosmetics helps protect the skin from environmental stressors, maintaining a youthful and healthy complexion.
Skin Protection: L-Ergothioneine (EGT) is widely used in cosmetics as an antioxidant, especially in skincare products. By scavenging free radicals, it effectively reduces oxidative stress, mitigates skin damage, and decreases signs of aging caused by UV exposure. EGT also enhances the resistance of skin cells, reducing DNA, protein, and lipid damage, aiding in DNA repair, increasing cell survival, and promoting skin health. As a natural antioxidant ingredient, EGT's application in cosmetics helps protect the skin from environmental stressors, maintaining its youthful and healthy appearance.
Preventing UV-induced ROS Damage: L-Ergothioneine (EGT) is a natural antioxidant found in food plants and tissues exposed to relatively high levels of oxidative stress. Compared to coenzyme Q10 as an antioxidant analogue, both are widely used in skincare products, but their relative efficacy has been lacking detailed descriptions. Studies suggest that OCTN-1, a specific receptor/transporter protein for EGT, is present in cultured human fibroblast cells and easily detectable. EGT shows higher efficiency in inhibiting lipid peroxidation compared to coenzyme Q10, and samples treated with EGT exhibit significantly fewer peroxides within 120 minutes after the addition of the antioxidant H2O2 when compared to those treated with coenzyme Q10. Additionally, EGT captures reactive oxygen species (ROS) more rapidly and effectively after exposure to UVA340 irradiation. Thus, due to the presence of OCTN-1 in fibroblast cells, EGT is considered a natural skin antioxidant. Relative to coenzyme Q10 and idebenone, EGT directly eliminates free radicals more efficiently, protecting cells from UV-induced ROS damage.
Delaying Skin Aging: L-Ergothioneine (EGT) is a sulfur-containing amino acid regarded as a natural antioxidant in nature. This unique amino acid has the ability to eliminate free radicals while also protecting cells from oxidative stress induced by UV radiation. In related studies, EGT was found to eliminate superoxide radicals (•O2–) and singlet oxygen (1O2). In cell cultures, EGT successfully inhibited the upregulation of tumor necrosis factor-α (TNF-α) induced by UVB irradiation. Furthermore, EGT significantly inhibited approximately 50% of matrix metalloproteinase-1 (MMP-1) protein expression in fibroblasts exposed to UV-A and reduced the expression levels of MMP-1 mRNA. This study suggests that EGT can eliminate reactive oxygen species generated by type I and type II photosensitization while inhibiting the expression of TNF-α and MMP-1, thereby reducing the aging effects induced by UV radiation.
Skin Care and Anti-Photoaging Ingredient: Changes associated with aging at the cellular level are often closely related to the physiological status of mitochondria. In these changes, a common type of mitochondrial DNA damage is the so-called "common deletion," referring to the loss of 4977 base pairs in mitochondrial DNA. In skin cells, this phenomenon is typically caused by UV-induced oxidative damage to mitochondrial DNA. The aim of the study was to assess the impact of the antioxidant L-Ergothioneine on UV-induced skin cell damage. The study also focused on the influence of L-Ergothioneine on the levels of reduced glutathione and detected the presence of "common deletions" in human fibroblast cells through polymerase chain reaction. The results showed that L-Ergothioneine increased intracellular levels of reduced glutathione and effectively protected cells from UV-induced mitochondrial DNA "common deletions." Considering the overall study results, L-Ergothioneine could be an effective component in skin care and anti-photoaging formulations.
Protecting Epidermal Keratinocytes: L-Ergothioneine has long been considered a potent and stable low-molecular-weight antioxidant. Humans intake L-Ergothioneine through diet, and it accumulates in cells that typically experience high levels of oxidative stress. However, as L-Ergothioneine cannot penetrate cell membranes, its protective function is limited to cells expressing the specific receptor/transporter protein OCTN1 for L-Ergothioneine. It has been observed that epidermal keratinocytes in skin cells also have the ability to synthesize OCTN1, allowing them to internalize and accumulate L-Ergothioneine. This accumulation imparts stronger antioxidant capabilities to cells, reducing levels of reactive oxygen species, DNA, proteins, and lipid damage in epidermal keratinocytes under simulated solar UV oxidative stress. L-Ergothioneine not only prevents oxidative damage but also potentially promotes cell DNA repair under UV radiation. This reduces oxidative damage to cellular components, limits apoptotic responses, and improves cell survival. The ability of cells to absorb, accumulate, and utilize the potent antioxidant L-Ergothioneine makes this natural amino acid and its receptor/transporter protein vital components of the skin's antioxidant defense system.
Application in the Biopharmaceuticals Industry
L-Ergothioneine (EGT) finds extensive applications in the field of biopharmaceuticals. EGT demonstrates potential antioxidant and anti-inflammatory effects, particularly in the treatment of type 2 diabetes and its complications. Studies have indicated that the use of EGT alone or in combination with metformin can reduce kidney and liver damage, improve blood glucose control, decrease oxidative stress, and mitigate inflammatory responses, offering potential relief from complications associated with type 2 diabetes. Further research is still needed to address issues such as the therapeutic dosage of EGT, the regulatory mechanisms of the OCTN1 receptor, and its impact on intestinal microbiota.
Potential Antioxidant and Anti-Inflammatory Effects: L-Ergothioneine (EGT) finds extensive application in the biopharmaceutical field, showing potential antioxidant and anti-inflammatory effects, especially in the treatment of type 2 diabetes and its complications. Research indicates that EGT, either alone or in combination with metformin, can reduce kidney and liver damage, improve blood glucose control, decrease oxidative stress and inflammatory responses, potentially alleviating complications associated with type 2 diabetes. Further research is needed to address issues such as the therapeutic dosage of EGT, the regulatory mechanisms of the OCTN1 receptor, and its impact on gut microbiota.
Alleviating Renal Function Impairment: L-Ergothioneine (L-EGT) is an approved supplement by the Food and Drug Administration (FDA), possessing cellular protection, antioxidant, and anti-inflammatory properties. A study investigated its renal protective effect in a rat model of type 2 diabetes (T2D), assessing the protective effects of L-EGT alone or in combination with metformin on renal damage in a T2D rat model induced by fructose-streptozotocin. The results demonstrated that L-EGT, alone or in combination with metformin, could alleviate renal function impairment, lower hyperglycemia, improve therapeutic effects, and enhance the expression of antioxidant and anti-inflammatory genes. Therefore, the combined use of L-EGT and metformin may serve as an adjunct therapy for alleviating renal damage in type 2 diabetes.
Treatment of Hepatic Complications: A study evaluated the hepatoprotective effects of L-Ergothioneine (L-EGT) alone and in combination with metformin in rats with type 2 diabetes (T2D). The results indicated that L-EGT alone or in combination with metformin could reduce liver enlargement, liver damage, triglyceride levels, oxidative stress, and inflammation in rats with T2D. Additionally, the co-administration of L-EGT and metformin in diabetic rats led to a reduction in blood glucose and insulin resistance. These research findings support the potential role of L-EGT in the treatment of liver complications associated with T2D.
Addressing UV-Induced Cellular Responses: Ergothioneine (EGT), a sulfur-containing amino acid, is considered to have natural antioxidant properties. The aim of this study was to determine the nature of its antioxidant activity and investigate the impact of EGT on UV-induced cellular responses. In chemical studies, EGT scavenged superoxide anion radicals (O-2(-)) and singlet oxygen (O-1(2)). In cultured fibroblast cells, EGT inhibited the upregulation of TNF-α following UVB irradiation. Furthermore, in fibroblast cells exposed to UV-A, EGT inhibited the expression of matrix metalloproteinase-1 (MMP-1) protein by nearly 50% and reduced the expression of MMP-1 mRNA. From these results, it can be concluded that EGT clears reactive oxygen species generated by type I and type II photosensitization and inhibits the transcriptional expression of TNF-α and MMP-1. EGT may reduce the anti-aging effects of skin after UV radiation by clearing O-2(-) and O-1(2), thereby limiting the signals of proteases and inflammation activity.
Preventing Oxidative Stress-Related Diseases: Ergothioneine (EGT), as a natural antioxidant, has shown remarkable potential in the treatment or prevention of oxidative stress-related diseases. Its antioxidant function is significantly superior to other natural antioxidants. Despite widespread use in the pharmaceutical and cosmetic industries, challenges still exist in the application of EGT. These challenges include researching other potentially beneficial components in mushrooms, clarifying the relationship between the therapeutic dosage of EGT and diseases, exploring the regulatory mechanisms of OCTN1 expression, and revealing other potential mechanisms of action for EGT. Additionally, more research is needed to understand the impact of EGT on gut microbiota.
Food Industry Applications:
Ergothioneine (EGT) has obtained novel food approval in Europe, confirming its safety in the food industry. Relevant studies have estimated the daily intake of EGT from novel foods in various age groups, and the results indicate levels below the established safe threshold (NOAEL). Furthermore, research highlights the preventive effects of EGT on embryonic development abnormalities in diabetic pregnant mice, supporting its use as an indicator for milk heat treatment. This series of research findings solidify the position of EGT as a safe and effective ingredient in the field of food.
Ergothioneine (EGT) has obtained novel food approval in Europe, confirming its safety in the food industry. Relevant studies have estimated the daily intake of EGT from novel foods in various age groups, and the results indicate levels below the established safe threshold (NOAEL). Furthermore, research highlights the preventive effects of EGT on embryonic development abnormalities in diabetic pregnant mice, supporting its use as an indicator for milk heat treatment. This series of research findings solidify the position of EGT as a safe and effective ingredient in the field of food.
Studies have estimated the daily intake of L-Ergothioneine from Novel Foods for various age groups, finding it to be below the no-observed-adverse-effect level (NOAEL). Furthermore, research highlights the preventive effects of L-Ergothioneine on embryonic development abnormalities in diabetic pregnant mice and supports its use as an indicator for milk heat treatment. These studies affirm the status of L-Ergothioneine as a safe and effective ingredient in the food industry.
In response to the European Commission's request, the Panel on Dietetic Products, Nutrition, and Allergies (NDA) assessed the supplementary dietary intake and safety of synthetic L-Ergothioneine as a Novel Food. The committee estimated the maximum daily intake of L-Ergothioneine from Novel Foods for various population groups, in addition to background dietary intake. The results indicated that the proposed use of synthetic L-Ergothioneine in Novel Foods for infants, children, and adults (including pregnant and lactating women) is safe. The safety margins were considered large enough for infants (284), children (236), and adults (including pregnant and lactating women, with a margin of 610). Therefore, the committee concluded that the proposed use of synthetic L-Ergothioneine as a Novel Food is safe for infants, children, pregnant women, and lactating women.
Reproductive Safety Studies: Reproductive safety of naturally occurring L-Ergothioneine was evaluated in rats through dietary intake. Daily supplementation of diabetic pregnant rats with 1.147 mg/kg body weight of L-Ergothioneine during the first 10 weeks of pregnancy reduced the incidence of embryo malformations, approaching levels observed in non-diabetic animals. L-Ergothioneine did not affect plasma glucose levels in diabetic and control animals. The conclusion drawn was that L-Ergothioneine plays a crucial role in antioxidant prevention by inhibiting glucose-mediated free radical-dependent embryonic malformations, potentially assisting in managing diabetes-induced embryonic lesions, especially when combined with vitamin E.
Impact on Embryonic Development: The study investigated the effects of the natural antioxidant ergothioneine on embryonic development abnormalities in diabetic pregnant mice. Supplementation of 1.147 mg/kg body weight of L-Ergothioneine to diabetic pregnant mice for only the first 11.5 days of pregnancy successfully reduced the incidence of embryonic malformations to levels similar to non-diabetic animals. L-Ergothioneine had no impact on plasma glucose levels in both diabetic and control animals. The conclusion was that L-Ergothioneine plays a crucial role in antioxidant prevention by inhibiting glucose-mediated free radical-dependent embryonic malformations, potentially assisting in managing diabetes-induced embryonic lesions, especially when combined with vitamin E.
Indicator for Milk Heat Treatment: A highly efficient and sensitive high-performance liquid chromatography (HILIC-UPLC) method was developed to determine L-Ergothioneine (ERT) in commercial milk. After derivatization of ERT, chromatographic separation was achieved using a Waters Cortecs UPLC HILIC 1.6 μm column with a mixture of 30 mmol/L ammonium acetate/acetonitrile (10:90, v/v) as the isocratic mobile phase, in less than 5 minutes. The detection and quantification limits were 0.03 and 0.10 μmol/L, respectively. The method exhibited linearity in the concentration range of 0.16 to 5.08 μmol/L. The average detected concentration of ERT in different categories of commercial milk was 0.442 ± 0.191 μmol/L, with the highest content in ultra-high-temperature-treated milk and lower levels in untreated and high-temperature short-time full-fat milk. The study suggests that ERT can serve as an indicator for milk heat treatment.
L-(+) Ergothioneine is a naturally occurring thiol amino acid with antioxidant properties and potential benefits as a dietary supplement. Recent research has investigated its toxicology and mutagenic potential, with results indicating that L-(+) Ergothioneine and its natural biomimetic did not demonstrate toxicity or mutagenicity in various experiments, including bacterial mutation tests and animal experiments. Therefore, the substance exhibits good tolerance in animals at recommended doses, supporting its potential as a safe dietary supplement.
Other applications:
For organ transplantation: The preservation quantity and time of existing tissues plays a decisive role in the success of organ transplantation surgery. Glutathione is the most widely used antioxidant for preserving organs for transplantation. However, when exposed to the environment, it is easily oxidized. Even under refrigerated or liquid conditions, its antioxidant capacity is greatly reduced, causing toxicity to cells and inflammation, inducing proteolysis of tissues. Ergothioneine is an antioxidant that is stable in aqueous solution and can also chelate heavy metal ions. In the field of organ protection, it can serve as an alternative to glutathione to better achieve organ transplant protection.
Ophthalmological applications: In recent years, research has discovered that ergothioneine plays a critical role in protecting the eyes. Therefore, many researchers hope to develop an ophthalmic product to promote the development of ophthalmic surgical procedures. Ophthalmic surgery is generally performed locally, and the water solubility and stability of ergothioneine provide feasibility for such surgeries, with great application value.
References:
[1]. K. Bazela, et al. L-Ergothioneine Protects Skin Cells against UV-Induced Damage—A Preliminary Study. DOI:10.3390/COSMETICS1010051
[2]. Kei Obayashi, et al. L-Ergothioneine scavenges superoxide and singlet oxygen and suppresses TNF-alpha and MMP-1 expression in UV-irradiated human dermal fibroblasts. DOI:10.1111/J.0142-5463.2005.00265_2.X
[3]. K. Dong, et al. A comparison of the relative antioxidant potency of L‐ergothioneine and idebenone. DOI:10.1111/j.1473-2165.2007.00330.x
[4]. N. Markova, et al. Skin cells and tissue are capable of using L-ergothioneine as an integral component of their antioxidant defense system. DOI:10.1016/j.freeradbiomed.2009.01.021
[5]. A. Dare, et al. L-ergothioneine and its combination with metformin attenuates renal dysfunction in type-2 diabetic rat model by activating Nrf2 antioxidant pathway. DOI:10.1016/j.biopha.2021.111921
[6]. A. Dare, et al. L-ergothioneine and metformin alleviates liver injury in experimental type-2 diabetic rats via reduction of oxidative stress, inflammation, and hypertriglyceridemia. DOI:10.21203/RS.3.RS-480961/V1
[7]. Kei Obayashi, et al. L-Ergothioneine scavenges superoxide and singlet oxygen and suppresses TNF-alpha and MMP-1 expression in UV-irradiated human dermal fibroblasts. DOI:10.1111/J.0142-5463.2005.00265_2.X
[8]. Tong-Tong Fu, et al. Ergothioneine as a Natural Antioxidant Against Oxidative Stress-Related Diseases. DOI:10.3389/fphar.2022.850813
[9]. D. Turck, et al. Safety of synthetic l-ergothioneine (Ergoneine®) as a novel food pursuant to Regulation (EC) No 258/97. DOI:10.2903/J.EFSA.2016.4629
[10]. D. Turck, et al. Statement on the safety of synthetic l‐ergothioneine as a novel food – supplementary dietary exposure and safety assessment for infants and young children, pregnant and breastfeeding women. DOI:10.2903/j.efsa.2017.5060
[11]. R. Forster, et al. Reproductive safety evaluation of L-Ergothioneine. DOI:10.1016/j.fct.2015.02.019
[12]. M. Guijarro, et al. Effects of ergothioneine on diabetic embryopathy in pregnant rats. DOI:10.1016/S0278-6915(02)00177-1
[13]. S. Sotgia, et al. Ultra-performance liquid chromatographic determination of L-ergothioneine in commercially available classes of cow milk. DOI:10.1111/1750-3841.12564
[14]. P. Marone, et al. A Safety Evaluation of a Nature-Identical l-Ergothioneine in Sprague Dawley Rats. DOI:10.1177/1091581816653375