Mimosine (BioDeep_00000000787)
Secondary id: BioDeep_00000398734
human metabolite PANOMIX_OTCML-2023 blood metabolite Chemicals and Drugs
代谢物信息卡片
化学式: C8H10N2O4 (198.064054)
中文名称: 含羞草碱
谱图信息:
最多检出来源 Macaca mulatta(otcml) 0.16%
分子结构信息
SMILES: C1=CN(C=C(C1=O)O)CC(C(=O)O)N
InChI: InChI=1S/C8H10N2O4/c9-5(8(13)14)3-10-2-1-6(11)7(12)4-10/h1-2,4-5,12H,3,9H2,(H,13,14)/t5-/m0/s1
描述信息
Mimosine is only found in individuals that have used or taken this drug. It is an antineoplastic alanine-substituted pyridine derivative isolated from Leucena glauca. [PubChem]Mimosine causes inhibition of DNA replication, changes in the progression of the cells in the cell cycle, and apoptosis. Mimosine appears to introduce breaks into DNA. Mimosine is an iron/zinc chelator. Iron depletion induces DNA double-strand breaks in treated cells, and activates a DNA damage response that results in focal phosphorylation of histones. This leads to inhibition of DNA replication and/or DNA elongation. Some studies indicate that mimosine prevents the initiation of DNA replication, whereas other studies indicate that mimosine disrupts elongation of the replication fork by impairing deoxyribonucleotide synthesis by inhibiting the activity of the iron-dependent enzyme ribonucleotide reductase and the transcription of the cytoplasmic serine hydroxymethyltransferase gene (SHMT). Inhibition of serine hydroxymethyltransferase is moderated by a zinc responsive unit located in front of the SHMT gene.
L-mimosine is an L-alpha-amino acid that is propionic acid substituted by an amino group at position 2 and a 3-hydroxy-4-oxopyridin-1(4H)-yl group at position 3 (the 2S-stereoisomer). It a non-protein plant amino acid isolated from Mimosa pudica. It has a role as an EC 1.14.18.1 (tyrosinase) inhibitor and a plant metabolite. It is a non-proteinogenic L-alpha-amino acid and a member of 4-pyridones. It is functionally related to a propionic acid. It is a conjugate acid of a L-mimosine(1-). It is a tautomer of a L-mimosine zwitterion.
Mimosine is an antineoplastic alanine-substituted pyridine derivative isolated from Leucena glauca.
3-Hydroxy-4-oxo-1(4H)-pyridinealanine. An antineoplastic alanine-substituted pyridine derivative isolated from Leucena glauca.
An L-alpha-amino acid that is propionic acid substituted by an amino group at position 2 and a 3-hydroxy-4-oxopyridin-1(4H)-yl group at position 3 (the 2S-stereoisomer). It a non-protein plant amino acid isolated from Mimosa pudica.
Mimosine, a tyrosine analog , can act as an antioxidant by its potent iron-binding activity[1]. Mimosine is a known chelator of Fe(III)[2]. Mimosine induces apoptosis through metal ion chelation, mitochondrial activation and ROS production in human leukemic cells[3]. Anti-cancer, antiinflammation.
Mimosine, a tyrosine analog , can act as an antioxidant by its potent iron-binding activity[1]. Mimosine is a known chelator of Fe(III)[2]. Mimosine induces apoptosis through metal ion chelation, mitochondrial activation and ROS production in human leukemic cells[3]. Anti-cancer, antiinflammation.
同义名列表
39 个代谢物同义名
1(4H)-Pyridinepropanoic acid, .alpha.-amino-3-hydroxy-4-oxo-, (.alpha.S)-; (2S)-2-amino-3-(3-hydroxy-4-oxo-1,4-dihydropyridin-1-yl)propanoic acid; 1(4H)-Pyridinepropanoic acid, alpha-amino-3-hydroxy-4-oxo-, (alphaS)-; 1(4H)-Pyridinepropanoic acid, alpha-amino-3-hydroxy-4-oxo-, (S)-; (2S)-2-azaniumyl-3-(4-hydroxy-3-oxidopyridinium-1-yl)propanoate; (2S)-2-amino-3-(3-hydroxy-4-oxopyridin-1(4H)-yl)propanoic acid; (S)-2-Amino-3-(3-hydroxy-4-oxopyridin-1(4H)-yl)propanoic acid; (S)-2-Amino-3-(3-hydroxy-4-oxo-4H-pyridin-1-yl)propanoic acid; (2S)-2-Amino-3-[3-hydroxy-4-oxo-1(4H)-pyridyl]propanoic acid; (S)-alpha-Amino-3-hydroxy-4-oxo-1(4H)-pyridylpropionic acid; (2S)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoic acid; (S)-2-Amino-3-(3-hydroxy-4-oxo-4H-pyridin-1-yl)propanoate; (2S)-2-amino-3-(3-hydroxy-4-oxo-1-pyridyl)propanoic acid; 3-(3-hydroxy-4-oxopyridin-1(4H)-yl)-L-alanine; L-Mimosine from Koa hoale seeds, >=98\\%; L-Mimosine from Koa hoale seeds; WZNJWVWKTVETCG-YFKPBYRVSA-N; MIMOSINE [WHO-DD]; Prestwick3_000379; UNII-Z46B1LUI5N; BPBio1_000591; MIMOSINE [MI]; Minosine, L-; (L)-MIMOSINE; Tox21_501238; Bio1_001334; Bio1_000845; Bio1_000356; L-Leucinine; L-mimosine; Leucaenine; Z46B1LUI5N; 1-mimosine; Leucaenol; AI3-51821; Leucenine; Leucenol; Mimosine; Mimosin
数据库引用编号
21 个数据库交叉引用编号
- ChEBI: CHEBI:29063
- KEGG: C04771
- PubChem: 440473
- HMDB: HMDB0015188
- Metlin: METLIN43986
- DrugBank: DB01055
- ChEMBL: CHEMBL245416
- Wikipedia: Mimosine
- MeSH: Mimosine
- ChemIDplus: 0000500447
- MetaCyc: AMINO-ETCETERA-PYRIDIN-1-YL-PROPANOATE
- KNApSAcK: C00001383
- chemspider: 389405
- CAS: 500-44-7
- medchemexpress: HY-N0928
- PMhub: MS000012824
- MetaboLights: MTBLC29063
- PubChem: 7336
- PDB-CCD: MMS
- NIKKAJI: J9.396C
- RefMet: Mimosine
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
3 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
- Mizael Machado, Cintia R R Queiroz-Machado, Dale R Gardner, Márcio B Castro, Antônio Carlos L Câmara, Luciano A Pimentel, Glauco J N Galiza, Franklin Riet-Correa. Leucaena leucocephala toxicity in Brazilian horses.
Toxicon : official journal of the International Society on Toxinology.
2024 Mar; 240(?):107655. doi:
10.1016/j.toxicon.2024.107655
. [PMID: 38382883] - Isis Machado Hueza, Vanius Vinicius Dipe, André Tadeu Gotardo, Dale R Gardner, Elaine Renata Motta de Almeida, Silvana Lima Górniak. Potential immunomodulatory response associated with L-mimosine in male Wistar rats.
Toxicon : official journal of the International Society on Toxinology.
2023 Apr; 226(?):107084. doi:
10.1016/j.toxicon.2023.107084
. [PMID: 36905965] - Einar Artiles-Ortega, Pedro Yoelvys de la Fé-Rodríguez, Beydis Reguera-Barreto, Raciel Lima-Orozco, Veerle Fievez. In vitro rumen degradability of tropical legumes and their secondary metabolites depends on inoculum source.
Tropical animal health and production.
2022 Sep; 54(5):330. doi:
10.1007/s11250-022-03327-z
. [PMID: 36173493] - Amal Widaad, Ihsan Nazurah Zulkipli, Mark I R Petalcorin. Anthelmintic Effect of Leucaena leucocephala Extract and Its Active Compound, Mimosine, on Vital Behavioral Activities in Caenorhabditis elegans.
Molecules (Basel, Switzerland).
2022 Mar; 27(6):. doi:
10.3390/molecules27061875
. [PMID: 35335240] - Kelly Cristine da Silva Rodrigues-Honda, Michael David Hideo Honda, Dulal Borthakur, Arthur G Fett-Neto. Methods of Mimosine Extraction from Leucaena leucocephala (Lam.) de Wit Leaves.
Methods in molecular biology (Clifton, N.J.).
2022; 2469(?):231-237. doi:
10.1007/978-1-0716-2185-1_19
. [PMID: 35508843] - André Tadeu Gotardo, Vânius Vinicius Dipe, Elaine Renata Motta de Almeida, Isis Machado Hueza, James Alan Pfister, Silvana Lima Górniak. Potential toxic effects produced by L-mimosine in the thyroid and reproductive systems. Evaluation in male rats.
Toxicon : official journal of the International Society on Toxinology.
2021 Nov; 203(?):121-128. doi:
10.1016/j.toxicon.2021.10.003
. [PMID: 34662629] - Sotiris Kyriakou, William Cheung, Theodora Mantso, Melina Mitsiogianni, Ioannis Anestopoulos, Stephany Veuger, Dimitris T Trafalis, Rodrigo Franco, Aglaia Pappa, David Tetard, Mihalis I Panayiotidis. A novel methylated analogue of L-Mimosine exerts its therapeutic potency through ROS production and ceramide-induced apoptosis in malignant melanoma.
Investigational new drugs.
2021 08; 39(4):971-986. doi:
10.1007/s10637-021-01087-5
. [PMID: 33624234] - Jaime N Wertman, Nicole Melong, Matthew R Stoyek, Olivia Piccolo, Stewart Langley, Benno Orr, Shelby L Steele, Babak Razaghi, Jason N Berman. The identification of dual protective agents against cisplatin-induced oto- and nephrotoxicity using the zebrafish model.
eLife.
2020 07; 9(?):. doi:
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. [PMID: 32720645] - Michael D H Honda, Dulal Borthakur. Mimosine facilitates metallic cation uptake by plants through formation of mimosine-cation complexes.
Plant molecular biology.
2020 Mar; 102(4-5):431-445. doi:
10.1007/s11103-019-00956-1
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Journal of plant research.
2020 Jan; 133(1):95-108. doi:
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. [PMID: 31828681] - Akm Moyeenul Huq, Lam Kok Wai, Kamal Rullah, Mohd Fadhlizil Fasihi Mohd Aluwi, Johnson Stanslas, Jamia Azdina Jamal. Oestrogenic activity of mimosine on MCF-7 breast cancer cell line through the ERα-mediated pathway.
Chemical biology & drug design.
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2019 Mar; 132(2):263-271. doi:
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. [PMID: 30637553] - Kelly Cristine da Silva Rodrigues-Corrêa, Michael D H Honda, Dulal Borthakur, Arthur Germano Fett-Neto. Mimosine accumulation in Leucaena leucocephala in response to stress signaling molecules and acute UV exposure.
Plant physiology and biochemistry : PPB.
2019 Feb; 135(?):432-440. doi:
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Applied biochemistry and biotechnology.
2018 Nov; 186(3):613-632. doi:
10.1007/s12010-018-2745-z
. [PMID: 29691793] - Yiwen Xu, Lin Cai. L‑mimosine induces caspase‑9‑mediated apoptosis in human osteosarcoma cells.
Molecular medicine reports.
2018 03; 17(3):4695-4701. doi:
10.3892/mmr.2018.8403
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Journal of plant research.
2018 Mar; 131(2):319-329. doi:
10.1007/s10265-017-0986-5
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BioMed research international.
2018; 2018(?):5872865. doi:
10.1155/2018/5872865
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2017 Apr; 15(4):1847-1852. doi:
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Physiology & behavior.
2016 10; 164(Pt A):1-10. doi:
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Oncotarget.
2016 08; 7(34):54317-54328. doi:
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International journal of molecular medicine.
2016 Feb; 37(2):533-41. doi:
10.3892/ijmm.2016.2452
. [PMID: 26744072] - Vishal Singh Negi, Dulal Borthakur. Heterologous Expression and Characterization of Mimosinase from Leucaena leucocephala.
Methods in molecular biology (Clifton, N.J.).
2016; 1405(?):59-77. doi:
10.1007/978-1-4939-3393-8_7
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Tropical animal health and production.
2015 Dec; 47(8):1481-6. doi:
10.1007/s11250-015-0887-3
. [PMID: 26210396] - Ann M Fallon. Effects of mimosine on Wolbachia in mosquito cells: cell cycle suppression reduces bacterial abundance.
In vitro cellular & developmental biology. Animal.
2015 Oct; 51(9):958-63. doi:
10.1007/s11626-015-9918-7
. [PMID: 26019119] - Binh Cao Quan Nguyen, Jamnian Chompoo, Shinkichi Tawata. Insecticidal and Nematicidal Activities of Novel Mimosine Derivatives.
Molecules (Basel, Switzerland).
2015 Sep; 20(9):16741-56. doi:
10.3390/molecules200916741
. [PMID: 26389870] - Graham Crawford, Birgit Puschner, Verena Affolter, Ilse Stalis, Autumn Davidson, Tomas Baker, John Tahara, Alison Jolly, Susan Ostapak. Systemic effects of Leucaena leucocephala ingestion on ringtailed lemurs (Lemur catta) at Berenty Reserve, Madagascar.
American journal of primatology.
2015 Jun; 77(6):633-41. doi:
10.1002/ajp.22386
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Kidney international.
2015 Apr; 87(4):761-70. doi:
10.1038/ki.2014.362
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Plant & cell physiology.
2014 May; 55(5):913-27. doi:
10.1093/pcp/pcu026
. [PMID: 24492257] - Shinjiro Ogita, Misako Kato, Shin Watanabe, Hiroshi Ashihara. The co-occurrence of two pyridine alkaloids, mimosine and trigonelline, in Leucaena leucocephala.
Zeitschrift fur Naturforschung. C, Journal of biosciences.
2014 Mar; 69(3-4):124-32. doi:
10.5560/znc.2013-0137
. [PMID: 24873033] - Vishal Singh Negi, Jon-Paul Bingham, Qing X Li, Dulal Borthakur. A carbon-nitrogen lyase from Leucaena leucocephala catalyzes the first step of mimosine degradation.
Plant physiology.
2014 Feb; 164(2):922-34. doi:
10.1104/pp.113.230870
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Archives of animal nutrition.
2013 Jun; 67(3):169-84. doi:
10.1080/1745039x.2013.801139
. [PMID: 23742642] - Yi Fang, Xiaofang Yu, Yong Liu, Alison J Kriegel, Yanyan Heng, Xialian Xu, Mingyu Liang, Xiaoqiang Ding. miR-29c is downregulated in renal interstitial fibrosis in humans and rats and restored by HIF-α activation.
American journal of physiology. Renal physiology.
2013 May; 304(10):F1274-82. doi:
10.1152/ajprenal.00287.2012
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Tropical animal health and production.
2012 Dec; 44(8):1873-8. doi:
10.1007/s11250-012-0150-0
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Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association.
2012 Aug; 27(8):3110-9. doi:
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. [PMID: 22399494] - Kiyoshi Nokihara, Akiyoshi Hirata, Tetsuya Sogon, Takafumi Ohyama. Preparative scale isolation, purification and derivatization of mimosine, a non-proteinogenic amino acid.
Amino acids.
2012 Jul; 43(1):475-82. doi:
10.1007/s00726-011-1104-y
. [PMID: 21993536] - Thongsuk Jetana, Sirima Thongruay, Sawong Uswang, Runchuan Hengtrakulsin. A comparative study on mimosine, 3,4-dihydroxy pyridone (3,4-DHP) and 2,3-dihydroxy pyridone (2,3-DHP), purine derivatives (PD) excretion in the urine, thyroid hormone and blood metabolites profiles of Thai swamp buffalo (Bubalus bubalis) and Murrah buffalo (Bubalus bubalis).
Tropical animal health and production.
2012 Apr; 44(4):887-97. doi:
10.1007/s11250-011-9983-1
. [PMID: 21928129] - Soon-Young Park, Jun-Sub Im, Sung-Rye Park, Sang-Eun Kim, Hoe-Jeong Wang, Joon-Kyu Lee. Mimosine arrests the cell cycle prior to the onset of DNA replication by preventing the binding of human Ctf4/And-1 to chromatin via Hif-1α activation in HeLa cells.
Cell cycle (Georgetown, Tex.).
2012 Feb; 11(4):761-6. doi:
10.4161/cc.11.4.19209
. [PMID: 22374673] - Shanlou Qiao, Keiko Murakami, Qinghong Zhao, Baoling Wang, Hisao Seo, Hitoshi Yamashita, Xiaotao Li, Takashi Iwamoto, Masatoshi Ichihara, Masataka Yoshino. Mimosine-induced apoptosis in C6 glioma cells requires the release of mitochondria-derived reactive oxygen species and p38, JNK activation.
Neurochemical research.
2012 Feb; 37(2):417-27. doi:
10.1007/s11064-011-0628-6
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Nephrology (Carlton, Vic.).
2012 Jan; 17(1):58-67. doi:
10.1111/j.1440-1797.2011.01498.x
. [PMID: 21777345] - Atul Upadhyay, Jamnian Chompoo, Nozomi Taira, Masakazu Fukuta, Shinichi Gima, Shinkichi Tawata. Solid-phase synthesis of mimosine tetrapeptides and their inhibitory activities on neuraminidase and tyrosinase.
Journal of agricultural and food chemistry.
2011 Dec; 59(24):12858-63. doi:
10.1021/jf203494t
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Pharmaceutical biology.
2010 Jun; 48(6):716-21. doi:
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BMC cell biology.
2010 Apr; 11(?):26. doi:
10.1186/1471-2121-11-26
. [PMID: 20398392] - Sandro L R Jube, Dulal Borthakur. Transgenic Leucaena leucocephala expressing the Rhizobium gene pydA encoding a meta-cleavage dioxygenase shows reduced mimosine content.
Plant physiology and biochemistry : PPB.
2010 Apr; 48(4):273-8. doi:
10.1016/j.plaphy.2010.01.005
. [PMID: 20138776] - Panlada Tittabutr, Jonathan D Awaya, Qing X Li, Dulal Borthakur. The cloned 1-aminocyclopropane-1-carboxylate (ACC) deaminase gene from Sinorhizobium sp. strain BL3 in Rhizobium sp. strain TAL1145 promotes nodulation and growth of Leucaena leucocephala.
Systematic and applied microbiology.
2008 Jun; 31(2):141-50. doi:
10.1016/j.syapm.2008.03.001
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Journal of the American Society of Nephrology : JASN.
2008 Jan; 19(1):39-46. doi:
10.1681/asn.2006090998
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Phytotherapy research : PTR.
2007 Nov; 21(11):1076-81. doi:
10.1002/ptr.2216
. [PMID: 17661331] - Mario Galindo, Rachel A Kahler, Nadiya M Teplyuk, Janet L Stein, Jane B Lian, Gary S Stein, Jennifer J Westendorf, Andre J van Wijnen. Cell cycle related modulations in Runx2 protein levels are independent of lymphocyte enhancer-binding factor 1 (Lef1) in proliferating osteoblasts.
Journal of molecular histology.
2007 Oct; 38(5):501-6. doi:
10.1007/s10735-007-9143-0
. [PMID: 17885813] - K Lalitha, S R Kulothungan. Mimosine mitigates oxidative stress in selenium deficient seedlings of Vigna radiata. Part II: mitochondrial uptake of 75selenium and mimosine.
Biological trace element research.
2007 Sep; 118(3):269-86. doi:
10.1007/s12011-007-0032-x
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Journal of chemical ecology.
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