Meta-Tyrosine (BioDeep_00000003083)

 

Secondary id: BioDeep_00001868717, BioDeep_00001883315

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


(2S)-2-Azaniumyl-3-(3-hydroxyphenyl)propanoate

化学式: C9H11NO3 (181.0738896)
中文名称: DL-m-酪氨酸, L-间酪氨酸
谱图信息: 最多检出来源 Viridiplantae(plant) 0.07%

分子结构信息

SMILES: C1=CC(=CC(=C1)O)CC(C(=O)O)N
InChI: InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-2-1-3-7(11)4-6/h1-4,8,11H,5,10H2,(H,12,13)

描述信息

Meta-Tyrosine, or M-Tyrosine for short, is a natural weed suppressant found in certain Fine fescue grass. M-tyrosine exudes out of the grass plants roots and is then absorbed by neighbouring weed seedlings. The weed plants will either die or be stunted from the toxic acid.
DL-m-Tyrosine shows effects on Arabidopsis root growth. Carbidopa combination with DL-m-tyrosine shows a potent hypotensive effect[1][2].

同义名列表

9 个代谢物同义名

(2S)-2-Azaniumyl-3-(3-hydroxyphenyl)propanoate; (2S)-2-amino-3-(3-hydroxyphenyl)propanoic acid; 3-(m-hydroxyphenyl)-L-alanine; Meta-Tyrosine; m-Tyrosine; L-m-Tyr; L-MTyr; DL-m-Tyrosine; L-m-Tyrosine



数据库引用编号

20 个数据库交叉引用编号

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

  • Geraldine Gueron, Nicolás Anselmino, Paula Chiarella, Emiliano G Ortiz, Sofia Lage Vickers, Alejandra V Paez, Jimena Giudice, Mario D Contin, Daiana Leonardi, Felipe Jaworski, Verónica Manzano, Ariel Strazza, Daniela R Montagna, Estefania Labanca, Javier Cotignola, Norma D Accorso, Anna Woloszynska-Read, Nora Navone, Roberto P Meiss, Raúl Ruggiero, Elba Vazquez. Game-changing restraint of Ros-damaged phenylalanine, upon tumor metastasis. Cell death & disease. 2018 02; 9(2):140. doi: 10.1038/s41419-017-0147-8. [PMID: 29396431]
  • Olga Andrzejczak, Urszula Krasuska, Joanna Olechowicz, Paweł Staszek, Katarzyna Ciacka, Renata Bogatek, Kim Hebelstrup, Agnieszka Gniazdowska. Destabilization of ROS metabolism in tomato roots as a phytotoxic effect of meta-tyrosine. Plant physiology and biochemistry : PPB. 2018 Feb; 123(?):369-377. doi: 10.1016/j.plaphy.2017.12.024. [PMID: 29304482]
  • Urszula Krasuska, Olga Andrzejczak, Paweł Staszek, Wojciech Borucki, Agnieszka Gniazdowska. meta-Tyrosine induces modification of reactive nitrogen species level, protein nitration and nitrosoglutathione reductase in tomato roots. Nitric oxide : biology and chemistry. 2017 Aug; 68(?):56-67. doi: 10.1016/j.niox.2016.10.008. [PMID: 27810375]
  • Stefano Dall'Acqua, Matteo Stocchero, Irene Boschiero, Mariano Schiavon, Samuel Golob, Jalal Uddin, Dario Voinovich, Stefano Mammi, Elisabetta Schievano. New findings on the in vivo antioxidant activity of Curcuma longa extract by an integrated (1)H NMR and HPLC-MS metabolomic approach. Fitoterapia. 2016 Mar; 109(?):125-31. doi: 10.1016/j.fitote.2015.12.013. [PMID: 26712080]
  • Damián Machuca, Paula Chiarella, Daniela Montagna, Graciela Dran, Roberto P Meiss, Raúl A Ruggiero. Meta-tyrosine. A powerful anti-metastatic factor with undetectable toxic-side effects. Medicina. 2015; 75(1):1-5. doi: . [PMID: 25637892]
  • Tengfang Huang, Ludmila Rehak, Georg Jander. meta-Tyrosine in Festuca rubra ssp. commutata (Chewings fescue) is synthesized by hydroxylation of phenylalanine. Phytochemistry. 2012 Mar; 75(?):60-6. doi: 10.1016/j.phytochem.2011.09.018. [PMID: 22192329]
  • Raúl A Ruggiero, Juan Bruzzo, Paula Chiarella, Oscar D Bustuoabad, Roberto P Meiss, Christiane D Pasqualini. Concomitant tumor resistance: the role of tyrosine isomers in the mechanisms of metastases control. Cancer research. 2012 Mar; 72(5):1043-50. doi: 10.1158/0008-5472.can-11-2964. [PMID: 22315349]
  • Yusuke Iwasaki, Keisuke Mochizuki, Yuki Nakano, Natsumi Maruya, Masato Goto, Yosuke Maruyama, Rie Ito, Koichi Saito, Hiroyuki Nakazawa. Comparison of fluorescence reagents for simultaneous determination of hydroxylated phenylalanine and nitrated tyrosine by high-performance liquid chromatography with fluorescence detection. Biomedical chromatography : BMC. 2012 Jan; 26(1):41-50. doi: 10.1002/bmc.1623. [PMID: 21387354]
  • Raúl A Ruggiero, Juan Bruzzo, Paula Chiarella, Pedro di Gianni, Martín A Isturiz, Susana Linskens, Norma Speziale, Roberto P Meiss, Oscar D Bustuoabad, Christiane D Pasqualini. Tyrosine isomers mediate the classical phenomenon of concomitant tumor resistance. Cancer research. 2011 Nov; 71(22):7113-24. doi: 10.1158/0008-5472.can-11-0581. [PMID: 22084446]
  • Nady Braidy, Gilles J Guillemin, Hussein Mansour, Tailoi Chan-Ling, Anne Poljak, Ross Grant. Age related changes in NAD+ metabolism oxidative stress and Sirt1 activity in wistar rats. PloS one. 2011 Apr; 6(4):e19194. doi: 10.1371/journal.pone.0019194. [PMID: 21541336]
  • Ruei-Lan Tsai, Bing-Ying Ho, Tzu-Ming Pan. Red Mold Rice Mitigates Oral Carcinogenesis in 7,12-Dimethyl-1,2-Benz[a]anthracene-Induced Oral Carcinogenesis in Hamster. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):245209. doi: 10.1093/ecam/nep215. [PMID: 20019075]
  • Tengfang Huang, Takayuki Tohge, Anna Lytovchenko, Alisdair R Fernie, Georg Jander. Pleiotropic physiological consequences of feedback-insensitive phenylalanine biosynthesis in Arabidopsis thaliana. The Plant journal : for cell and molecular biology. 2010 Sep; 63(5):823-35. doi: 10.1111/j.1365-313x.2010.04287.x. [PMID: 20598094]
  • Harleen Kaur, Rajwant Kaur, Surinder Kaur, Ian T Baldwin, Inderjit. Taking ecological function seriously: soil microbial communities can obviate allelopathic effects of released metabolites. PloS one. 2009; 4(3):e4700. doi: 10.1371/journal.pone.0004700. [PMID: 19277112]
  • Cécile Bertin, Leslie A Weston, Tengfang Huang, Georg Jander, Thomas Owens, Jerrold Meinwald, Frank C Schroeder. Grass roots chemistry: meta-tyrosine, an herbicidal nonprotein amino acid. Proceedings of the National Academy of Sciences of the United States of America. 2007 Oct; 104(43):16964-9. doi: 10.1073/pnas.0707198104. [PMID: 17940026]
  • Chutima Matayatsuk, Anne Poljak, Sonia Bustamante, George A Smythe, Ruchaneekorn W Kalpravidh, Pornpan Sirankapracha, Suthat Fucharoen, Prapin Wilairat. Quantitative determination of ortho- and meta-tyrosine as biomarkers of protein oxidative damage in beta-thalassemia. Redox report : communications in free radical research. 2007; 12(5):219-28. doi: 10.1179/135100007x200272. [PMID: 17925094]
  • Ping-Ho Chen, Chi-Cheng Tsai, Ying-Chu Lin, Ying-Chin Ko, Yi-Hsin Yang, Tien-Yu Shieh, Pei-Shan Ho, Chien-Ming Li, Albert Min-Shan Ko, Chung-Ho Chen. Ingredients contribute to variation in production of reactive oxygen species by areca quid. Journal of toxicology and environmental health. Part A. 2006 Jun; 69(11):1055-69. doi: 10.1080/15287390500360224. [PMID: 16840253]
  • Philip H Elsinga, Kentaro Hatano, Kiichi Ishiwata. PET tracers for imaging of the dopaminergic system. Current medicinal chemistry. 2006; 13(18):2139-53. doi: 10.2174/092986706777935258. [PMID: 16918344]
  • Subramaniam Pennathur, Yasuo Ido, Jozsef I Heller, Jaeman Byun, Ratna Danda, Pablo Pergola, Joseph R Williamson, Jay W Heinecke. Reactive carbonyls and polyunsaturated fatty acids produce a hydroxyl radical-like species: a potential pathway for oxidative damage of retinal proteins in diabetes. The Journal of biological chemistry. 2005 Jun; 280(24):22706-14. doi: 10.1074/jbc.m500839200. [PMID: 15855169]
  • Tobias Böttcher, Hao Ren, Michel Goiny, Joachim Gerber, Jens Lykkesfeldt, Ulrich Kuhnt, Miriam Lotz, Stephanie Bunkowski, Carola Werner, Ingmar Schau, Annette Spreer, Stephan Christen, Roland Nau. Clindamycin is neuroprotective in experimental Streptococcus pneumoniae meningitis compared with ceftriaxone. Journal of neurochemistry. 2004 Dec; 91(6):1450-60. doi: 10.1111/j.1471-4159.2004.02837.x. [PMID: 15584921]
  • Brian Reed, Nianhang Chen, Joseph B Justice. Dual-electrode voltammetry of catecholamine transport: simultaneous monitoring of uptake and efflux. Journal of neuroscience methods. 2003 Jun; 126(2):127-35. doi: 10.1016/s0165-0270(03)00073-6. [PMID: 12814837]
  • Mark M Huycke, Danny R Moore. In vivo production of hydroxyl radical by Enterococcus faecalis colonizing the intestinal tract using aromatic hydroxylation. Free radical biology & medicine. 2002 Sep; 33(6):818-26. doi: 10.1016/s0891-5849(02)00977-2. [PMID: 12208369]
  • P Dandona, P Mohanty, W Hamouda, H Ghanim, A Aljada, R Garg, V Kumar. Inhibitory effect of a two day fast on reactive oxygen species (ROS) generation by leucocytes and plasma ortho-tyrosine and meta-tyrosine concentrations. The Journal of clinical endocrinology and metabolism. 2001 Jun; 86(6):2899-902. doi: 10.1210/jcem.86.6.7745. [PMID: 11397907]
  • S Pennathur, J D Wagner, C Leeuwenburgh, K N Litwak, J W Heinecke. A hydroxyl radical-like species oxidizes cynomolgus monkey artery wall proteins in early diabetic vascular disease. The Journal of clinical investigation. 2001 Apr; 107(7):853-60. doi: 10.1172/jci11194. [PMID: 11285304]
  • C H Magsino, W Hamouda, V Bapna, H Ghanim, I A Abu-Reish, A Aljada, P Dandona. Nadolol inhibits reactive oxygen species generation by leukocytes and linoleic acid oxidation. The American journal of cardiology. 2000 Aug; 86(4):443-8. doi: 10.1016/s0002-9149(00)00962-0. [PMID: 10946040]
  • C H Magsino, W Hamouda, H Ghanim, R Browne, A Aljada, P Dandona. Effect of triiodothyronine on reactive oxygen species generation by leukocytes, indices of oxidative damage, and antioxidant reserve. Metabolism: clinical and experimental. 2000 Jun; 49(6):799-803. doi: 10.1053/meta.2000.6263. [PMID: 10877210]
  • L G Flores, K Kawai, M Nakagawa, N Shikano, S Jinnouchi, S Tamura, K Watanabe, A Kubodera. A new radiopharmaceutical for the cerebral dopaminergic presynaptic function: 6-radioiodinated L-meta-tyrosine. Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism. 2000 Jan; 20(1):207-12. doi: 10.1097/00004647-200001000-00026. [PMID: 10616810]
  • S Ishimitsu, S Fujimoto, A Ohara. High-performance liquid chromatographic determination of m-tyrosine and o-tyrosine in rat urine. Journal of chromatography. 1989 Apr; 489(2):377-83. doi: 10.1016/s0378-4347(00)82917-5. [PMID: 2753962]
  • D J Edwards, D Sorisio, S Knopf, S Mujumdar. Assay for L-p-tyrosine in plasma and brain by column liquid chromatography with electrochemical detection using m-tyrosine as the internal standard. Journal of chromatography. 1986 Nov; 383(1):142-7. doi: 10.1016/s0378-4347(00)83452-0. [PMID: 3818832]
  • S Ishimitsu, S Fujimoto, A Ohara. Determination of m-tyrosine and o-tyrosine in human serum by high-performance liquid chromatography with fluorimetric detection. Journal of chromatography. 1986 May; 378(1):222-5. doi: 10.1016/s0378-4347(00)80716-1. [PMID: 3733974]
  • J A Hoskins, A M Greenway. The metabolism of L-m-tyrosine: the use of a putative precursor to investigate the increased production of m-hydroxymandelic acid in phenylketonuria. Clinica chimica acta; international journal of clinical chemistry. 1983 Jun; 130(3):329-38. doi: 10.1016/0009-8981(83)90307-8. [PMID: 6872265]
  • J H Tong, R G Smyth, N L Benoiton, A D'Iorio. In vivo studies on the conversion of m-tyrosine to 3,4-dihydroxyphenylalanine in the rat. Canadian journal of biochemistry. 1977 Oct; 55(10):1103-7. doi: 10.1139/o77-163. [PMID: 912602]