Ergothioneine (BioDeep_00000018451)
Main id: BioDeep_00000003122
Secondary id: BioDeep_00000405812
human metabolite PANOMIX_OTCML-2023 blood metabolite Volatile Flavor Compounds
代谢物信息卡片
alpha-Carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium hydroxide inner salt
化学式: C9H15N3O2S (229.088493)
中文名称: 麦角硫因
谱图信息:
最多检出来源 Chinese Herbal Medicine(otcml) 0.65%
Reviewed
Last reviewed on 2024-09-14.
Cite this Page
Ergothioneine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China.
https://query.biodeep.cn/s/ergothioneine (retrieved
2024-11-22) (BioDeep RN: BioDeep_00000018451). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
分子结构信息
SMILES: C[N+](C)(C)C(CC1=CNC(=S)N1)C(=O)[O-]
InChI: 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)/p+1
描述信息
Ergothioneine is a naturally occurring metabolite of histidine that has antioxidant properties. -- Pubchem. Ergothioneine is a product of plant origin that accumulates in animal tissues. Ergothioneine is biosynthesized exclusively by fungi and mycobacteria and is captured by plants through their roots. As an ingredient of human food, ET is distributed very unevenly. By far, the highest levels of Ergothioneine have been found in mushrooms (0.1-1 mg/g dried material). Ergothioneine is rapidly cleared from the circulation and then avidly retained with minimal metabolism: the whole-body half-life of ingested Ergothioneine in rats is 1 month. The content of Ergothioneine varies greatly among tissues and is strongly dependent on its dietary level. In addition to erythrocytes and bone marrow, high Ergothioneine levels have also been found in seminal fluid. The precise physiological role of ET has remained elusive since its discovery in 1909. It is known that Ergothioneine is a powerful scavenger of hydroxyl radicals and an inhibitor of iron or copper ion-dependent generation of hydroxyl radicals from hydrogen peroxide (H2O2). A specific ergothioneine transporter has recently been identified (gene symbol SLC22A4 - PMID: 15795384). Ergothioneine appears to play a pivotal protective role in monocytes, because the occurrence of rheumatoid arthritis and Crohns disease has very recently been linked to variant ergothioneine transporter genes (PMID: 15795384). SLC22A4 is highly expressed in the kidney, where it is thought to aid in active secretion of organic cations, and may facilitate the active reabsorption of ergothioneine.
A naturally occurring metabolite of histidine that has antioxidant properties. -- Pubchem. Ergothioneine is a product of plant origin that accumulates in animal tissues. Ergothioneine is biosynthesized exclusively by fungi and mycobacteria and is captured by plants through their roots. As an ingredient of human food, ET is distributed very unevenly. By far, the highest levels of Ergothioneine have been found in mushrooms (0.1-1 mg/g dried material). Ergothioneine is rapidly cleared from the circulation and then avidly retained with minimal metabolism: the whole-body half-life of ingested Ergothioneine in rats is 1 month. The content of Ergothioneine varies greatly among tissues and is strongly dependent on its dietary level. In addition to erythrocytes and bone marrow, high Ergothioneine levels have also been found in seminal fluid. The precise physiological role of ET has remained elusive since its discovery in 1909. It is known that Ergothioneine is a powerful scavenger of hydroxyl radicals and an inhibitor of iron or copper ion-dependent generation of hydroxyl radicals from hydrogen peroxide (H2O2). A specific ergothioneine transporter has recently been identified (gene symbol SLC22A4 - PMID: 15795384). Ergothioneine appears to play a pivotal protective role in monocytes, because the occurrence of rheumatoid arthritis and Crohns disease has very recently been linked to variant ergothioneine transporter genes (PMID: 15795384). SLC22A4 is highly expressed in the kidney, where it is thought to aid in active secretion of organic cations, and may facilitate the active reabsorption of ergothioneine.
D020011 - Protective Agents > D000975 - Antioxidants
Ergothioneine is an imidazole-2-thione derivative with orally active histidine betaine. Ergothioneine is a specific inhibitor of p38-MAPK and Akt, which plays a protective role in cell apoptosis induced by stress. Ergothioneine has antioxidant activity[1][2].
Ergothioneine, an imidazole-2-thione derivative of histidine betaine, is synthesized by certain bacteria and fungi. Ergothioneine is generally considered an antioxidant[1].
同义名列表
27 个代谢物同义名
alpha-Carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium hydroxide inner salt; (AlphaS)-alpha-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt; (AlphaS)-α-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt; (AlphaS)-a-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt; 3-(2-Sulphanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoic acid; 3-(2-Sulfanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoic acid; (S)-(1-Carboxy-2-(2-mercaptoimidazol-4-yl)ethyl)trimethylammonium hydroxide; 3-(2-Sulphanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoate; {5-[(2S)-2-carboxy-2-(trimethylazaniumyl)ethyl]-1H-imidazol-2-yl}sulfanide; 3-(2-Sulfanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoate; (2S)-3-(2-Mercapto-1H-imidazol-5-yl)-2-(trimethylammonio)propanoic acid; (2S)-3-(2-Mercapto-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate; 2-Mercaptohistidine trimethylbetaine; 2 Thiol L histidine betaine; 2-Thiol-L-histidine-betaine; Thiolhistidine-betaine; Thiolhistidinebetaine; Ergothioneine thiol; L-(+)-ERGOTHIONEINE; Erythrothioneine; L-Ergothioneine; Ergothioneine; Sympectothion; Ergothionine; L-Thioneine; Thioneine; Ergothioneine
数据库引用编号
21 个数据库交叉引用编号
- ChEBI: CHEBI:82707
- ChEBI: CHEBI:4828
- PubChem: 76551346
- PubChem: 5351619
- HMDB: HMDB0003045
- ChEMBL: CHEMBL5209630
- Wikipedia: Ergothioneine
- MeSH: Ergothioneine
- MetaCyc: CPD-15276
- KNApSAcK: C00053098
- foodb: FDB004217
- chemspider: 4508619
- CAS: 497-30-3
- PMhub: MS000008139
- RefMet: Ergothioneine
- medchemexpress: HY-N1914
- KEGG: C05570
- PubChem: 7896
- KNApSAcK: 4828
- LOTUS: LTS0190369
- wikidata: Q74411790
分类词条
相关代谢途径
Reactome(4)
BioCyc(0)
PlantCyc(0)
代谢反应
3 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(3)
- ergothioneine biosynthesis I (bacteria):
ergothioneine (thione form) ⟶ ergothioneine - ergothioneine biosynthesis II (fungi):
ergothioneine (thione form) ⟶ ergothioneine - ergothioneine biosynthesis I (bacteria):
ergothioneine (thione form) ⟶ ergothioneine
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Robert J Hondal. Selenium vitaminology: The connection between selenium, vitamin C, vitamin E, and ergothioneine.
Current opinion in chemical biology.
2023 May; 75(?):102328. doi:
10.1016/j.cbpa.2023.102328. [PMID: 37236134] - Yuting Zhang, Guizhu Cao, Xiaonan Li, Zhongyun Piao. Effects of Exogenous Ergothioneine on Brassica rapa Clubroot Development Revealed by Transcriptomic Analysis.
International journal of molecular sciences.
2023 Mar; 24(7):. doi:
10.3390/ijms24076380. [PMID: 37047350] - Dirk Gründemann, Lea Hartmann, Svenja Flögel. The ergothioneine transporter (ETT): substrates and locations, an inventory.
FEBS letters.
2022 May; 596(10):1252-1269. doi:
10.1002/1873-3468.14269. [PMID: 34958679] - Robert B Beelman, Allen T Phillips, John P Richie, Djibril M Ba, Sjoerd W Duiker, Michael D Kalaras. Health consequences of improving the content of ergothioneine in the food supply.
FEBS letters.
2022 05; 596(10):1231-1240. doi:
10.1002/1873-3468.14268. [PMID: 34954825] - William J Behof, Clayton A Whitmore, Justin R Haynes, Adam J Rosenberg, Mohammed N Tantawy, Todd E Peterson, Fiona E Harrison, Robert B Beelman, Printha Wijesinghe, Joanne A Matsubara, Wellington Pham. Improved synthesis of an ergothioneine PET radioligand for imaging oxidative stress in Alzheimer's disease.
FEBS letters.
2022 05; 596(10):1279-1289. doi:
10.1002/1873-3468.14303. [PMID: 35100442] - Li Wang, Yang Wang, Jianghua Li, Guocheng DU, Zhen Kang. [Construction and optimization of ergothioneine-producing Escherichia coli].
Sheng wu gong cheng xue bao = Chinese journal of biotechnology.
2022 Feb; 38(2):796-806. doi:
10.13345/j.cjb.210166. [PMID: 35234399] - Lan Pang, Ting Wang, Qian Liao, Yanfen Cheng, Di Wang, Jingjing Li, Chaomei Fu, Chen Zhang, Jinming Zhang. Protective role of ergothioneine isolated from Pleurotus ostreatus against dextran sulfate sodium-induced ulcerative colitis in rat model.
Journal of food science.
2022 Jan; 87(1):415-426. doi:
10.1111/1750-3841.15982. [PMID: 34873706] - Ayobami Dare, Ahmed A Elrashedy, Mahendra L Channa, Anand Nadar. Cardioprotective Effects and in-silico Antioxidant Mechanism of L-Ergothioneine in Experimental Type-2 Diabetic Rats.
Cardiovascular & hematological agents in medicinal chemistry.
2022; 20(2):133-147. doi:
10.2174/1871525719666210809122541. [PMID: 34370646] - Jaeyoung Choi, Eunsu Song, Hyeeun Gwon, Eunju Song, Michael D Kalaras, Robert B Beelman, Jinah Hwang. Aqueous Extracts of Pleurotus ostreatus and Hericium erinaceus Protect against Ultraviolet A-Induced Damage in Human Dermal Fibroblasts.
International journal of medicinal mushrooms.
2022; 24(2):63-74. doi:
10.1615/intjmedmushrooms.2021042348. [PMID: 35446523] - Liu-Yun Wu, Irwin K Cheah, Joyce Ruifen Chong, Yuek Ling Chai, Jia Yun Tan, Saima Hilal, Henri Vrooman, Christopher P Chen, Barry Halliwell, Mitchell K P Lai. Low plasma ergothioneine levels are associated with neurodegeneration and cerebrovascular disease in dementia.
Free radical biology & medicine.
2021 12; 177(?):201-211. doi:
10.1016/j.freeradbiomed.2021.10.019. [PMID: 34673145] - Sahar Abdalkarim Salih, Hossein Daghigh-Kia, Mahdieh Mehdipour, Abouzar Najafi. Does ergothioneine and thawing temperatures improve rooster semen post-thawed quality?.
Poultry science.
2021 Oct; 100(10):101405. doi:
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Scientific reports.
2021 09; 11(1):18450. doi:
10.1038/s41598-021-97925-w. [PMID: 34531467] - Ayobami Dare, Mahendra L Channa, Anand Nadar. L-ergothioneine and its combination with metformin attenuates renal dysfunction in type-2 diabetic rat model by activating Nrf2 antioxidant pathway.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2021 Sep; 141(?):111921. doi:
10.1016/j.biopha.2021.111921. [PMID: 34346315] - Samir A Salama, Gamil M Abd-Allah, Ahmed M Mohamadin, Mostafa M Elshafey, Hesham S Gad. Ergothioneine mitigates cisplatin-evoked nephrotoxicity via targeting Nrf2, NF-κB, and apoptotic signaling and inhibiting γ-glutamyl transpeptidase.
Life sciences.
2021 Aug; 278(?):119572. doi:
10.1016/j.lfs.2021.119572. [PMID: 33964294] - Shohei Makiishi, Kengo Furuichi, Yuta Yamamura, Keisuke Sako, Yasuyuki Shinozaki, Tadashi Toyama, Shinji Kitajima, Yasunori Iwata, Norihiko Sakai, Miho Shimizu, Tomoko Hirose-Sugiura, Shuichi Kaneko, Yukio Kato, Takashi Wada. Carnitine/organic cation transporter 1 precipitates the progression of interstitial fibrosis through oxidative stress in diabetic nephropathy in mice.
Scientific reports.
2021 04; 11(1):9093. doi:
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International journal of molecular sciences.
2021 Mar; 22(6):. doi:
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Neuromolecular medicine.
2021 03; 23(1):184-198. doi:
10.1007/s12017-020-08620-4. [PMID: 33067719] - Stefano Fornasaro, Elisa Gurian, Sofia Pagarin, Elena Genova, Gabriele Stocco, Giuliana Decorti, Valter Sergo, Alois Bonifacio. Ergothioneine, a dietary amino acid with a high relevance for the interpretation of label-free surface enhanced Raman scattering (SERS) spectra of many biological samples.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.
2021 Feb; 246(?):119024. doi:
10.1016/j.saa.2020.119024. [PMID: 33049471] - Noritaka Nakamichi, Shunsuke Nakao, Misa Nishiyama, Yuka Takeda, Takahiro Ishimoto, Yusuke Masuo, Satoshi Matsumoto, Makoto Suzuki, Yukio Kato. Oral Administration of the Food-Derived Hydrophilic Antioxidant Ergothioneine Enhances Object Recognition Memory in Mice.
Current molecular pharmacology.
2021; 14(2):220-233. doi:
10.2174/1874467213666200212102710. [PMID: 32048982] - Julia Tschirka, Markus Bach, Ilmars Kisis, Julia Lemmen, Mark Jean Gnoth, Dirk Gründemann. Transporter tandems: precise tools for normalizing active transporter in the plasma membrane.
The Biochemical journal.
2020 11; 477(21):4191-4206. doi:
10.1042/bcj20200666. [PMID: 33073844] - Misa Nishiyama, Noritaka Nakamichi, Tomoyuki Yoshimura, Yusuke Masuo, Tomoe Komori, Takahiro Ishimoto, Jun-Ichi Matsuo, Yukio Kato. Homostachydrine is a Xenobiotic Substrate of OCTN1/SLC22A4 and Potentially Sensitizes Pentylenetetrazole-Induced Seizures in Mice.
Neurochemical research.
2020 Nov; 45(11):2664-2678. doi:
10.1007/s11064-020-03118-8. [PMID: 32844295] - Yoshiki Matsuda, Nobuyuki Ozawa, Takiko Shinozaki, Ken-Ichi Wakabayashi, Kosuke Suzuki, Yusuke Kawano, Iwao Ohtsu, Yoshitaka Tatebayashi. Ergothioneine, a metabolite of the gut bacterium Lactobacillus reuteri, protects against stress-induced sleep disturbances.
Translational psychiatry.
2020 05; 10(1):170. doi:
10.1038/s41398-020-0855-1. [PMID: 32467627] - Einar Smith, Filip Ottosson, Sophie Hellstrand, Ulrika Ericson, Marju Orho-Melander, Céline Fernandez, Olle Melander. Ergothioneine is associated with reduced mortality and decreased risk of cardiovascular disease.
Heart (British Cardiac Society).
2020 05; 106(9):691-697. doi:
10.1136/heartjnl-2019-315485. [PMID: 31672783] - Rachel D Williamson, Fergus P McCarthy, Samprikta Manna, Emer Groarke, Douglas B Kell, Louise C Kenny, Cathal M McCarthy. L-(+)-Ergothioneine Significantly Improves the Clinical Characteristics of Preeclampsia in the Reduced Uterine Perfusion Pressure Rat Model.
Hypertension (Dallas, Tex. : 1979).
2020 02; 75(2):561-568. doi:
10.1161/hypertensionaha.119.13929. [PMID: 31865793] - Pachara Thananurak, Napapach Chuaychu-Noo, Aurore Thélie, Yupin Phasuk, Thevin Vongpralub, Elisabeth Blesbois. Different concentrations of cysteamine, ergothioneine, and serine modulate quality and fertilizing ability of cryopreserved chicken sperm.
Poultry science.
2020 Feb; 99(2):1185-1198. doi:
10.1016/j.psj.2019.10.040. [PMID: 32029149] - Aude-Claire Morillon, Rachel D Williamson, Philip N Baker, Douglas B Kell, Louise C Kenny, Jane A English, Fergus P McCarthy, Cathal McCarthy. Effect of L-Ergothioneine on the metabolic plasma profile of the RUPP rat model of pre-eclampsia.
PloS one.
2020; 15(3):e0230977. doi:
10.1371/journal.pone.0230977. [PMID: 32231385] - Robert B Beelman, Michael D Kalaras, Allen T Phillips, John P Richie. Is ergothioneine a 'longevity vitamin' limited in the American diet?.
Journal of nutritional science.
2020; 9(?):e52. doi:
10.1017/jns.2020.44. [PMID: 33244403] - Raquel G Loreto, David P Hughes. The metabolic alteration and apparent preservation of the zombie ant brain.
Journal of insect physiology.
2019 10; 118(?):103918. doi:
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Free radical biology & medicine.
2019 09; 141(?):34-46. doi:
10.1016/j.freeradbiomed.2019.05.034. [PMID: 31163255] - Jade Pahila, Yuki Ishikawa, Toshiaki Ohshima. Effects of Ergothioneine-Rich Mushroom Extract on the Oxidative Stability of Astaxanthin in Liposomes.
Journal of agricultural and food chemistry.
2019 Mar; 67(12):3491-3501. doi:
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Journal of bioscience and bioengineering.
2018 Dec; 126(6):715-722. doi:
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FEBS letters.
2018 10; 592(20):3357-3366. doi:
10.1002/1873-3468.13123. [PMID: 29851075] - Kentaro Nishida, Kazuya Takeuchi, Ayami Hosoda, Shohei Sugano, Eri Morisaki, Akihiro Ohishi, Kazuki Nagasawa. Ergothioneine ameliorates oxaliplatin-induced peripheral neuropathy in rats.
Life sciences.
2018 Aug; 207(?):516-524. doi:
10.1016/j.lfs.2018.07.006. [PMID: 29981320] - Robert N Kerley, Cathal McCarthy, Douglas B Kell, Louise C Kenny. The potential therapeutic effects of ergothioneine in pre-eclampsia.
Free radical biology & medicine.
2018 03; 117(?):145-157. doi:
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Scientific reports.
2018 01; 8(1):1601. doi:
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International journal of medicinal mushrooms.
2018; 20(4):381-392. doi:
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Kidney international.
2017 12; 92(6):1356-1369. doi:
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Free radical biology & medicine.
2017 12; 113(?):385-394. doi:
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Food chemistry.
2017 Oct; 233(?):273-281. doi:
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Food chemistry.
2017 Oct; 233(?):429-433. doi:
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Scientific reports.
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Antioxidants & redox signaling.
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International journal of medicinal mushrooms.
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Biochemical and biophysical research communications.
2016 09; 478(1):162-167. doi:
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International journal of toxicology.
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Plant foods for human nutrition (Dordrecht, Netherlands).
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Biochimica et biophysica acta.
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Brain and behavior.
2016 06; 6(6):e00477. doi:
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Scientific reports.
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European journal of clinical investigation.
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Cell reports.
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Drug metabolism and pharmacokinetics.
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Free radical biology & medicine.
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Chembiochem : a European journal of chemical biology.
2015 Jan; 16(1):119-25. doi:
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International journal of medicinal mushrooms.
2015; 17(8):749-61. doi:
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International journal of medicinal mushrooms.
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Fungal genetics and biology : FG & B.
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Food chemistry.
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Free radical research.
2014 Sep; 48(9):1049-60. doi:
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Cryobiology.
2014 Aug; 69(1):68-73. doi:
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British journal of clinical pharmacology.
2014 Jul; 78(1):129-34. doi:
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PloS one.
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Molecular pharmaceutics.
2013 Jul; 10(7):2509-16. doi:
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Journal of mass spectrometry : JMS.
2013 Mar; 48(3):406-12. doi:
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PloS one.
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Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2012 Nov; 50(11):3902-11. doi:
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Preventive medicine.
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Preventive medicine.
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Fungal genetics and biology : FG & B.
2012 Feb; 49(2):160-72. doi:
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Journal of physiology and pharmacology : an official journal of the Polish Physiological Society.
2011 Aug; 62(4):411-9. doi:
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Cryobiology.
2011 Aug; 63(1):1-6. doi:
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Journal of bacteriology.
2011 Apr; 193(8):1981-90. doi:
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Chemical research in toxicology.
2011 Jan; 24(1):30-4. doi:
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Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2010 Dec; 48(12):3492-9. doi:
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Drug metabolism and disposition: the biological fate of chemicals.
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Cell death and differentiation.
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Journal of agricultural and food chemistry.
2010 Feb; 58(4):2577-85. doi:
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Reproductive sciences (Thousand Oaks, Calif.).
2009 Nov; 16(11):1040-51. doi:
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Free radical biology & medicine.
2009 Apr; 46(8):1168-76. doi:
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Journal of food science.
2009 Mar; 74(2):C162-9. doi:
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Journal of agricultural and food chemistry.
2008 Nov; 56(21):10032-40. doi:
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The Journal of surgical research.
2008 Jan; 144(1):36-42. doi:
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Journal of cosmetic dermatology.
2007 Sep; 6(3):183-8. doi:
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Journal of agricultural and food chemistry.
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Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
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Toxicology and applied pharmacology.
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Proceedings of the National Academy of Sciences of the United States of America.
2005 Apr; 102(14):5256-61. doi:
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The Journal of surgical research.
2004 Nov; 122(1):96-102. doi:
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Clinical nutrition (Edinburgh, Scotland).
2004 Apr; 23(2):183-93. doi:
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Free radical biology & medicine.
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Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
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The Biochemical journal.
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Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
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The Biochemical journal.
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