E7521
L-(+)-麦角硫因
别名:
2-巯基组氨酸三甲基甜菜碱, 硫代组氨酸甜菜碱, 硫因, 硫氨酸, 麦角硫因, 麦角硫碱, (S)-α-羧基-N,N,N-三甲基-2-巯基-1H-咪唑-4-乙酰胆碱 内盐
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关于此项目
经验公式（希尔记法）:
C9H15N3O2S
化学文摘社编号:
分子量:
229.30
NACRES:
NA.32
PubChem Substance ID:
UNSPSC Code:
12352209
EC Number:
207-843-5
MDL number:
InChI key
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
SMILES string
C[N+](C)(C)[C@@H](Cc1c[nH]c(S)n1)C([O-])=O
biological source
fungus (Actinomycetales), fungus (Ascomycota), fungus (Basidiomycota)
assay
≥98.0%
form
powder
mol wt
229.30
storage condition
(Keep container tightly closed in a dry and well-ventilated place)
technique(s)
protein quantification: suitable
solubility
water: 50 mg/mL, clear, colorless
storage temp.
−20°C
Quality Level
General description
L-(+)-麦角硫因(ET)是一种含硫氨基酸，仅由担子菌科和子囊菌科的放线菌和非酵母类真菌产生。它最初是从紫麦角菌或黑麦麦角菌中分离出来的。它是从L-组氨酸中获得的，该组氨酸被转化为甜菜碱形式，称为组氨酸甜菜碱。它存在于动物和植物中，哺乳动物通常从它们的饮食中获取，例如通过蘑菇或燕麦。它的性质是互变异构的，在中性水溶液中以硫酮形式存在。
研究领域：细胞凋亡
研究领域：细胞凋亡
Application
L-(+)-麦角硫因适用于研究它与2,2′- 和4,4′-联吡啶二硫化物（2-Py-S-S-2-Py和4-Py-S-S-4-Py）的反应性。它也可用于实验细胞的孵育，同时进行ATM（Ataxia毛细血管扩张症突变）或ATR （ATM-和RAD3-相关）的体外激酶活性测定。
L-(+)-麦角硫因已被用于：
L-(+)-麦角硫因已被用于：
- 作为卵丘-卵母细胞复合物(COC)成熟培养基的组成部分，检测其对脂质过氧化形成的保护作用
- 作为一种抗氧化化合物用于检测2型糖尿病患者
- 作为可溶性载体蛋白22A4 (SLC22A4)转运检测的阳性对照
Biochem/physiol Actions
L-(+)-麦角硫因(ET)在氧化应激组织中浓度最高，在血液、晶状体、骨髓、精液和肝脏中浓度最高。它是一种抗氧化剂，通过清除活性氧和活性氮，防止细胞凋亡。抗氧化活性主要来源于巯基。它是SLC22A4（溶质载体族22，成员4）转运体的底物。在肺泡巨噬细胞中，阻止肿瘤坏死因子(TNF)α释放白细胞介素-8 (IL-8)。IL-8是一种炎性细胞因子。它还能调节肝、肾的氧化损伤，并对脂质过氧化有保护作用。它还负责内源性谷胱甘肽和α-生育酚的保存。ET是一种抗氧化剂，可以抵御γ和紫外线辐射。在紫外线照射的人皮肤成纤维细胞中，它可以清除活性氧(ROS)，并抑制基质金属蛋白酶1 (MMP1)的表达。它还可能防止紫外线辐射引起的皮肤衰老。
Packaging
无底玻璃瓶。内含物装在锥底内插管中。
Other Notes
存在于紫锁骨菌中的天然氨基酸
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Irina Borodina et al.
Nutrition research reviews, 33(2), 190-217 (2020-02-14)
Ergothioneine (ERG) is an unusual thio-histidine betaine amino acid that has potent antioxidant activities. It is synthesised by a variety of microbes, especially fungi (including in mushroom fruiting bodies) and actinobacteria, but is not synthesised by plants and animals who
Substantial fibrin amyloidogenesis in type 2 diabetes assessed using amyloid-selective fluorescent stains
Pretorius E, et al.
Cardiovascular Diabetology, 16(1), 141-141 (2017)
J Carlsson et al.
The Biochemical journal, 139(1), 221-235 (1974-04-01)
1. The reactions of 2,2'- and 4,4'-dipyridyl disulphide (2-Py-S-S-2-Py and 4-Py-S-S-4-Py) with l-ergothioneine (2-mercapto-l-histidine betaine), 2-mercaptoimidazole, 1-methyl-2-mercaptoimidazole, thiourea, thioacetamide, 2-thiopyridone (Py-2-SH) and 4-thiopyridone (Py-4-SH) were investigated spectrophotometrically in the pH range approx. 1-9. 2. These reactions involve two sequential reversible
Monica Deiana et al.
Clinical nutrition (Edinburgh, Scotland), 23(2), 183-193 (2004-03-20)
L-ergothioneine is a fungal metabolite exhibiting antioxidant functions in cells. The aim of this study was to assess the effect of oral administration of L-ergothioneine on the oxidative damage in vivo caused by the Fenton reagent ferric-nitrilotriacetate. Rats were supplemented
Irwin K Cheah et al.
Biochimica et biophysica acta, 1822(5), 784-793 (2011-10-18)
Since its discovery, the unique properties of the naturally occurring amino acid, L-ergothioneine (EGT; 2-mercaptohistidine trimethylbetaine), have intrigued researchers for more than a century. This widely distributed thione is only known to be synthesized by non-yeast fungi, mycobacteria and cyanobacteria
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