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L-(+)-麦角硫因,L-(+)-Ergothioneine [ET];≥98.0%

别名:硫因;(S)-α-羧基-N,N,N-三甲基-2-巯基-1H-咪唑-4-乙胺内盐;Thioneine;(S)-α-Carboxy-N,N,N-trimethyl-2-mercapto-1H-imidazole-4-ethanaminium inner salt

Empirical Formula (Hill Notation): C9H15N3O2S CAS号: 497-30-3 分子量: 229.30 EC 号: 207-843-5 MDL编号: MFCD00167474 PubChem化学物质编号: 24894650 NACRES: NA.32
制造商品牌: 西格玛 Sigma-Aldrich
货号(SKU): E7521
CAS号: 497-30-3
MDL号: MFCD00167474
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¥1,615.90

说明

L-(+)-麦角硫因 (ET) 是一种含硫氨基酸,仅由属于担子菌门和子囊菌门的放线菌目细菌和非酵母类真菌产生。它最初是从 Claviceps purpurea 或黑麦麦角中分离出来的。它是从 L-组氨酸中获得的,L-组氨酸被转化为甜菜碱形式,称为海西宁。它存在于动物和植物中,哺乳动物通常从它们的饮食中获得它,例如通过蘑菇或燕麦。本质上是互变异构体,在中性水溶液中以硫酮形式存在。

L-(+)-麦角硫因适用于研究其与 2,2'- 和 4,4'-二吡啶基二硫化物(2-Py-S-S-2-Py 和 4-Py-S-S-4-)的反应性派)。它还可用于培养实验细胞,同时对 ATM(Ataxia telangiectasia mutated)或 ATR(ATM 和 RAD3 相关)进行体外激酶活性测定。


L-(+)-麦角硫因已用于:

作为卵丘-卵母细胞复合物 (COC) 成熟培养基的一种成分,以测试对脂质过氧化物形成的保护功能
作为一种抗氧化化合物来测试 2 型糖尿病患者
作为溶质载体蛋白 22 A4 (SLC22A4) 转运试验的阳性对照

L-(+)-麦角硫因 (ET) 在遭受氧化应激的组织中浓度最高,在血液、晶状体、骨髓、精液和肝脏中浓度最高。它通过清除活性氧和氮物质,起到抗氧化剂和防止细胞凋亡的作用。抗氧化活性归因于巯基。它充当 SLC22A4(溶质载体家族 22,成员 4)转运蛋白的底物。在肺泡巨噬细胞中,它阻止肿瘤坏死因子 (TNF)α 释放白细胞介素 8 (IL-8)。 IL-8 是一种炎症细胞因子。它还调节肝脏和肾脏的氧化损伤,并对脂质过氧化具有保护作用。它还负责保护内源性谷胱甘肽和α-生育酚。 ET 是一种抗氧化剂,可防止 γ 和紫外线辐射。在紫外线照射的人真皮成纤维细胞中,它清除活性氧 (ROS),并抑制基质金属蛋白酶 1 (MMP1) 的表达。它还可能对由紫外线辐射引起的皮肤产生抗衰老作用。

一般描述

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.
 

应用

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). It may also be used for the incubation of experimental cells while performing in vitro kinase activity assays for ATM (Ataxia telangiectasia mutated) or ATR (ATM- and RAD3-related).
L-(+)-Ergothioneine has been used:
  • as a component of the maturation medium for cumulus-oocyte complexes (COCs) to test protective function on lipid peroxide formation
  • as an antioxidant compound to test type 2 diabetes patients
  • as a positive control in solute carrier protein 22 A4 (SLC22A4) transport assay
  •  

生化/生理作用

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.
 

其他说明

Natural amino acid found in the fungus Claviceps purpurea
 
 

属性

质量水平

200

储存温度

−20°C

SMILES string

C[N+](C)(C)[C@@H](Cc1c[nH]c(S)n1)C([O-])=O

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

InChI key

SSISHJJTAXXQAX-ZETCQYMHSA-N

 

安全信息

储存分类代码

13 - Non Combustible Solids

WGK

WGK 3

个人防护装备

Eyeshields, Gloves, type N95 (US)

商品规格
属性名称属性值
储存温度 Storage temp.-20°C低温冷冻
全球实时库存 Availability √美国St. Louis ≥ 60 | 欧洲Eur. ≥ 21 | 東京Tokyo ≥ 5 | 香港与北京 ≥ 10