Xanthurenic acid (BioDeep_00000399992)

Main id: BioDeep_00000001489

Secondary id: BioDeep_00000412689

natural product PANOMIX_OTCML-2023 BioNovoGene_Lab2019


代谢物信息卡片


Xanthurenic acid

化学式: C10H7NO4 (205.0375)
中文名称: 黄尿酸, 黄原酸
谱图信息: 最多检出来源 Homo sapiens(plant) 27.53%

分子结构信息

SMILES: C1=CC2=C(C(=C1)O)NC(=CC2=O)C(=O)O
InChI: InChI=1S/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)

描述信息

A quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by hydroxy groups at C-4 and C-8.
D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents
D009676 - Noxae > D000963 - Antimetabolites
Xanthurenic acid is a putative endogenous Group II metabotropic glutamate receptor agonist, on sensory transmission in the thalamus.
Xanthurenic acid is a putative endogenous Group II metabotropic glutamate receptor agonist, on sensory transmission in the thalamus.

同义名列表

3 个代谢物同义名

Xanthurenic acid; Xanthurenic acid; Xanthurenic acid



数据库引用编号

75 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)

29 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。

亚细胞结构定位 关联基因列表
Cytoplasm 6 AHR, CASP3, CASP9, GSN, IDO1, KYNU
Nucleus 3 AHR, CASP3, CASP9
cytosol 9 AHR, CASP3, CASP9, GPT, GSN, IDO1, KMO, KYNU, TDO2
dendrite 1 GRM2
phagocytic vesicle 1 GSN
nucleoplasm 3 AHR, CASP3, KYNU
Cell membrane 3 GRM2, GRM3, TNF
lamellipodium 1 GSN
Multi-pass membrane protein 6 ABCC3, GRM2, GRM3, KMO, SLC22A6, SLC22A8
Synapse 1 GRM2
cell surface 1 TNF
glutamatergic synapse 3 CASP3, GRM2, GRM3
Golgi membrane 1 INS
neuronal cell body 2 CASP3, TNF
presynaptic membrane 2 GRM2, GRM3
Cytoplasm, cytosol 2 IDO1, KYNU
plasma membrane 8 ABCC3, GRM2, GRM3, GSN, IFNLR1, SLC22A6, SLC22A8, TNF
Membrane 6 ABCC3, GRM2, GRM3, IFNLR1, KMO, SLC22A6
apical plasma membrane 1 SLC22A8
axon 2 GRM2, GRM3
basolateral plasma membrane 3 ABCC3, SLC22A6, SLC22A8
caveola 1 SLC22A6
extracellular exosome 4 GPT, GSN, SLC22A6, SLC22A8
extracellular space 6 CRP, GSN, IL10, INS, KMO, TNF
mitochondrion 4 AADAT, CASP9, KMO, KYNU
protein-containing complex 3 AHR, CASP9, SLC22A6
postsynaptic density 2 CASP3, GRM3
Single-pass type I membrane protein 1 IFNLR1
Secreted 3 CRP, IL10, INS
extracellular region 5 CRP, GSN, IL10, INS, TNF
Mitochondrion outer membrane 1 KMO
mitochondrial outer membrane 1 KMO
mitochondrial matrix 1 AADAT
transcription regulator complex 1 AHR
external side of plasma membrane 1 TNF
actin cytoskeleton 1 GSN
dendritic spine 1 GRM3
sarcoplasm 1 GSN
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 2 GRM2, GRM3
Membrane raft 1 TNF
Cytoplasm, cytoskeleton 1 GSN
focal adhesion 1 GSN
lateral plasma membrane 1 SLC22A8
chromatin 1 AHR
stereocilium bundle 1 IDO1
phagocytic cup 1 TNF
cytoskeleton 1 GSN
podosome 1 GSN
blood microparticle 1 GSN
Basolateral cell membrane 3 ABCC3, SLC22A6, SLC22A8
endosome lumen 1 INS
aryl hydrocarbon receptor complex 1 AHR
Cell projection, dendrite 1 GRM2
basal plasma membrane 2 ABCC3, SLC22A6
ficolin-1-rich granule lumen 1 GSN
secretory granule lumen 2 GSN, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 1 INS
cortical actin cytoskeleton 1 GSN
actin cap 1 GSN
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
apoptosome 1 CASP9
Basal cell membrane 2 ABCC3, SLC22A6
death-inducing signaling complex 1 CASP3
astrocyte projection 2 GRM2, GRM3
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
smooth muscle contractile fiber 1 IDO1
nuclear aryl hydrocarbon receptor complex 1 AHR
cytosolic aryl hydrocarbon receptor complex 1 AHR
caspase complex 1 CASP9
interleukin-28 receptor complex 1 IFNLR1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Kai Tai Derek Yeung, Nicholas Penney, Luke Whiley, Hutan Ashrafian, Matthew R Lewis, Sanjay Purkayastha, Ara Darzi, Elaine Holmes. The impact of bariatric surgery on serum tryptophan-kynurenine pathway metabolites. Scientific reports. 2022 01; 12(1):294. doi: 10.1038/s41598-021-03833-4. [PMID: 34996930]
  • Isabel Schüle, Urs Berger, Uta Matysiak, Gunda Ruzaike, Brigitte Stiller, Martin Pohl, Ute Spiekerkoetter, Ekkehart Lausch, Sarah C Grünert, Miriam Schmidts. A Homozygous Deletion of Exon 5 of KYNU Resulting from a Maternal Chromosome 2 Isodisomy (UPD2) Causes Catel-Manzke-Syndrome/VCRL Syndrome. Genes. 2021 06; 12(6):. doi: 10.3390/genes12060879. [PMID: 34200361]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • M Karayama, J Masuda, K Mori, H Yasui, H Hozumi, Y Suzuki, K Furuhashi, T Fujisawa, N Enomoto, Y Nakamura, N Inui, T Suda, M Maekawa, H Sugimura, A Takada. Comprehensive assessment of multiple tryptophan metabolites as potential biomarkers for immune checkpoint inhibitors in patients with non-small cell lung cancer. Clinical & translational oncology : official publication of the Federation of Spanish Oncology Societies and of the National Cancer Institute of Mexico. 2021 Feb; 23(2):418-423. doi: 10.1007/s12094-020-02421-8. [PMID: 32533317]
  • Gioacchino Luca Losacco, Omar Ismail, Julian Pezzatti, Víctor González-Ruiz, Julien Boccard, Serge Rudaz, Jean-Luc Veuthey, Davy Guillarme. Applicability of Supercritical fluid chromatography-Mass spectrometry to metabolomics. II-Assessment of a comprehensive library of metabolites and evaluation of biological matrices. Journal of chromatography. A. 2020 Jun; 1620(?):461021. doi: 10.1016/j.chroma.2020.461021. [PMID: 32178859]
  • Romain Colle, Perrine Masson, Céline Verstuyft, Bruno Fève, Erwan Werner, Claire Boursier-Neyret, Bernard Walther, Denis J David, Bruno Boniface, Bruno Falissard, Philippe Chanson, Emmanuelle Corruble, Laurent Becquemont. Peripheral tryptophan, serotonin, kynurenine, and their metabolites in major depression: A case-control study. Psychiatry and clinical neurosciences. 2020 Feb; 74(2):112-117. doi: 10.1111/pcn.12944. [PMID: 31599111]
  • Karen M Ryan, Kelly A Allers, Declan M McLoughlin, Andrew Harkin. Tryptophan metabolite concentrations in depressed patients before and after electroconvulsive therapy. Brain, behavior, and immunity. 2020 01; 83(?):153-162. doi: 10.1016/j.bbi.2019.10.005. [PMID: 31606477]
  • Gregory Oxenkrug, Hans-Gert Bernstein, Paul C Guest, Marieke van der Hart, Julien Roeser, Paul Summergrad, Johann Steiner. Plasma xanthurenic acid in a context of insulin resistance and obesity in schizophrenia. Schizophrenia research. 2019 09; 211(?):98-99. doi: 10.1016/j.schres.2019.07.038. [PMID: 31383514]
  • Mengran Li, Chunxiao Wu, Hongbin Guo, Ce Chu, Mingye Hu, Chengyan Zhou. Mangiferin improves hepatic damage-associated molecular patterns, lipid metabolic disorder and mitochondrial dysfunction in alcohol hepatitis rats. Food & function. 2019 Jun; 10(6):3514-3534. doi: 10.1039/c9fo00153k. [PMID: 31144698]
  • Martina Curto, Luana Lionetto, Francesco Fazio, Valentina Corigliano, Anna Comparelli, Stefano Ferracuti, Maurizio Simmaco, Ferdinando Nicoletti, Ross J Baldessarini. Serum xanthurenic acid levels: Reduced in subjects at ultra high risk for psychosis. Schizophrenia research. 2019 06; 208(?):465-466. doi: 10.1016/j.schres.2019.02.020. [PMID: 30837204]
  • Jon Sigurd Sande, Arve Ulvik, Øivind Midttun, Per M Ueland, Hilde B Hammer, Merete Valen, Ellen M Apalset, Clara G Gjesdal. Vitamin B-6 Status Correlates with Disease Activity in Rheumatoid Arthritis Patients During Treatment with TNFα Inhibitors. The Journal of nutrition. 2019 05; 149(5):770-775. doi: 10.1093/jn/nxz001. [PMID: 31050750]
  • Maurizio Pompili, Luana Lionetto, Martina Curto, Alberto Forte, Denise Erbuto, Franco Montebovi, Maria Elena Seretti, Isabella Berardelli, Gianluca Serafini, Marco Innamorati, Mario Amore, Ross J Baldessarini, Paolo Girardi, Maurizio Simmaco. Tryptophan and Kynurenine Metabolites: Are They Related to Depression?. Neuropsychobiology. 2019; 77(1):23-28. doi: 10.1159/000491604. [PMID: 30110684]
  • Qing Tong, Jia Song, Guangjie Yang, Li Fan, Wei Xiong, Jianguo Fang. Simultaneous determination of tryptophan, kynurenine, kynurenic acid, xanthurenic acid and 5-hydroxytryptamine in human plasma by LC-MS/MS and its application to acute myocardial infarction monitoring. Biomedical chromatography : BMC. 2018 Apr; 32(4):. doi: 10.1002/bmc.4156. [PMID: 29193181]
  • Katsumi Shibata. Organ Co-Relationship in Tryptophan Metabolism and Factors That Govern the Biosynthesis of Nicotinamide from Tryptophan. Journal of nutritional science and vitaminology. 2018; 64(2):90-98. doi: 10.3177/jnsv.64.90. [PMID: 29710037]
  • Isidor Minović, Anna van der Veen, Martijn van Faassen, Ineke J Riphagen, Else van den Berg, Claude van der Ley, António W Gomes-Neto, Johanna M Geleijnse, Manfred Eggersdorfer, Gerjan J Navis, Ido P Kema, Stephan Jl Bakker. Functional vitamin B-6 status and long-term mortality in renal transplant recipients. The American journal of clinical nutrition. 2017 Dec; 106(6):1366-1374. doi: 10.3945/ajcn.117.164012. [PMID: 28978540]
  • Björn Gylling, Robin Myte, Jörn Schneede, Göran Hallmans, Jenny Häggström, Ingegerd Johansson, Arve Ulvik, Per M Ueland, Bethany Van Guelpen, Richard Palmqvist. Vitamin B-6 and colorectal cancer risk: a prospective population-based study using 3 distinct plasma markers of vitamin B-6 status. The American journal of clinical nutrition. 2017 04; 105(4):897-904. doi: 10.3945/ajcn.116.139337. [PMID: 28275126]
  • Therese Karlsson, Elin Strand, Jutta Dierkes, Christian A Drevon, Jannike Øyen, Øivind Midttun, Per M Ueland, Oddrun A Gudbrandsen, Eva Ringdal Pedersen, Ottar Nygård. Associations between intake of fish and n-3 long-chain polyunsaturated fatty acids and plasma metabolites related to the kynurenine pathway in patients with coronary artery disease. European journal of nutrition. 2017 Feb; 56(1):261-272. doi: 10.1007/s00394-015-1077-9. [PMID: 26482150]
  • Lasse Melvaer Giil, Øivind Midttun, Helga Refsum, Arve Ulvik, Rajiv Advani, A David Smith, Per Magne Ueland. Kynurenine Pathway Metabolites in Alzheimer's Disease. Journal of Alzheimer's disease : JAD. 2017; 60(2):495-504. doi: 10.3233/jad-170485. [PMID: 28869479]
  • Marie Favennec, Benjamin Hennart, Marie Verbanck, Marie Pigeyre, Robert Caiazzo, Violeta Raverdy, Hélène Verkindt, Audrey Leloire, Gilles J Guillemin, Loïc Yengo, Delphine Allorge, Philippe Froguel, François Pattou, Odile Poulain-Godefroy. Post-Bariatric Surgery Changes in Quinolinic and Xanthurenic Acid Concentrations Are Associated with Glucose Homeostasis. PloS one. 2016; 11(6):e0158051. doi: 10.1371/journal.pone.0158051. [PMID: 27327770]
  • Bhawana Sharma, Rajesh Dabur. Protective Effects of Tinospora cordifolia on Hepatic and Gastrointestinal Toxicity Induced by Chronic and Moderate Alcoholism. Alcohol and alcoholism (Oxford, Oxfordshire). 2016 Jan; 51(1):1-10. doi: 10.1093/alcalc/agv130. [PMID: 26589585]
  • Federica Gevi, Lello Zolla, Stefano Gabriele, Antonio M Persico. Urinary metabolomics of young Italian autistic children supports abnormal tryptophan and purine metabolism. Molecular autism. 2016; 7(?):47. doi: 10.1186/s13229-016-0109-5. [PMID: 27904735]
  • Francesco Fazio, Luana Lionetto, Martina Curto, Luisa Iacovelli, Michele Cavallari, Cristina Zappulla, Martina Ulivieri, Flavia Napoletano, Matilde Capi, Valentina Corigliano, Sergio Scaccianoce, Alessandra Caruso, Jessica Miele, Antonio De Fusco, Luisa Di Menna, Anna Comparelli, Antonella De Carolis, Roberto Gradini, Robert Nisticò, Antonio De Blasi, Paolo Girardi, Valeria Bruno, Giuseppe Battaglia, Ferdinando Nicoletti, Maurizio Simmaco. Xanthurenic Acid Activates mGlu2/3 Metabotropic Glutamate Receptors and is a Potential Trait Marker for Schizophrenia. Scientific reports. 2015 Dec; 5(?):17799. doi: 10.1038/srep17799. [PMID: 26643205]
  • Gregory F Oxenkrug. Increased Plasma Levels of Xanthurenic and Kynurenic Acids in Type 2 Diabetes. Molecular neurobiology. 2015 Oct; 52(2):805-10. doi: 10.1007/s12035-015-9232-0. [PMID: 26055228]
  • G G Meyramov, К-D Kohnert, А А Kikimbaeva, А М Аitkulov, Z T Кystaubaeva, G M Тykeshanova, O-N Dupont, Е М Laryushina, А G Меyramova, G O Zhuzbaeva, О L Коvalenko, A S Shaybek. Histological Changes in Pancreatic Islets of Animals with Experimental Diabetes Caused by Xanthurenic Acid under Condition of Suppression of Its Endogenous Synthesis. Bulletin of experimental biology and medicine. 2015 Sep; 159(5):680-4. doi: 10.1007/s10517-015-3046-y. [PMID: 26463059]
  • Hui Zuo, Per M Ueland, Simone J P M Eussen, Grethe S Tell, Stein E Vollset, Ottar Nygård, Øivind Midttun, Klaus Meyer, Arve Ulvik. Markers of vitamin B6 status and metabolism as predictors of incident cancer: the Hordaland Health Study. International journal of cancer. 2015 Jun; 136(12):2932-9. doi: 10.1002/ijc.29345. [PMID: 25404109]
  • Oana M Deac, James L Mills, Barry Shane, Øivind Midttun, Per M Ueland, John T Brosnan, Margaret E Brosnan, Eamon Laird, Eileen R Gibney, Ruzong Fan, Yifan Wang, Lawrence C Brody, Anne M Molloy. Tryptophan catabolism and vitamin B-6 status are affected by gender and lifestyle factors in healthy young adults. The Journal of nutrition. 2015 Apr; 145(4):701-7. doi: 10.3945/jn.114.203091. [PMID: 25833774]
  • Eva Ringdal Pedersen, Nora Tuseth, Simone J P M Eussen, Per Magne Ueland, Elin Strand, Gard Frodahl Tveitevåg Svingen, Øivind Midttun, Klaus Meyer, Gunnar Mellgren, Arve Ulvik, Jan Erik Nordrehaug, Dennis W Nilsen, Ottar Nygård. Associations of plasma kynurenines with risk of acute myocardial infarction in patients with stable angina pectoris. Arteriosclerosis, thrombosis, and vascular biology. 2015 Feb; 35(2):455-62. doi: 10.1161/atvbaha.114.304674. [PMID: 25524770]
  • Martina Curto, Luana Lionetto, Andrea Negro, Matilde Capi, Francesca Perugino, Francesco Fazio, Maria Adele Giamberardino, Maurizio Simmaco, Ferdinando Nicoletti, Paolo Martelletti. Altered serum levels of kynurenine metabolites in patients affected by cluster headache. The journal of headache and pain. 2015; 17(?):27. doi: 10.1186/s10194-016-0620-2. [PMID: 27000870]
  • Martina Curto, Luana Lionetto, Andrea Negro, Matilde Capi, Francesco Fazio, Maria Adele Giamberardino, Maurizio Simmaco, Ferdinando Nicoletti, Paolo Martelletti. Altered kynurenine pathway metabolites in serum of chronic migraine patients. The journal of headache and pain. 2015; 17(?):47. doi: 10.1186/s10194-016-0638-5. [PMID: 27130315]
  • Huawei Zhang, Peng Fu, Beilei Ke, Shuping Wang, Min Li, Lin Han, Chengcheng Peng, Weidong Zhang, Runhui Liu. Metabolomic analysis of biochemical changes in the plasma and urine of collagen-induced arthritis in rats after treatment with Huang-Lian-Jie-Du-Tang. Journal of ethnopharmacology. 2014 May; 154(1):55-64. doi: 10.1016/j.jep.2014.03.007. [PMID: 24709313]
  • Liqiang Gu, Xiaofan Wang, Yuanyuan Zhang, Yu Jiang, Huan Lu, Kaishun Bi, Xiaohui Chen. Determination of 12 potential nephrotoxicity biomarkers in rat serum and urine by liquid chromatography with mass spectrometry and its application to renal failure induced by Semen Strychni. Journal of separation science. 2014 May; 37(9-10):1058-66. doi: 10.1002/jssc.201400053. [PMID: 24610835]
  • Xiaowei Sun, Wei Xu, Yan Zeng, Yurong Hou, Lin Guo, Xiujuan Zhao, Changhao Sun. Metabonomics evaluation of urine from rats administered with phorate under long-term and low-level exposure by ultra-performance liquid chromatography-mass spectrometry. Journal of applied toxicology : JAT. 2014 Feb; 34(2):176-83. doi: 10.1002/jat.2848. [PMID: 23280859]
  • Yuichi Uwai, Yuta Nakashima, Emi Honjo, Tatsuya Kawasaki, Tomohiro Nabekura. Diuresis by intravenous administration of xanthurenic acid in rats, and inhibition by probenecid. Biomedical research (Tokyo, Japan). 2014; 35(3):223-6. doi: 10.2220/biomedres.35.223. [PMID: 24942862]
  • Arve Ulvik, Despoina Theofylaktopoulou, Øivind Midttun, Ottar Nygård, Simone J P M Eussen, Per M Ueland. Substrate product ratios of enzymes in the kynurenine pathway measured in plasma as indicators of functional vitamin B-6 status. The American journal of clinical nutrition. 2013 Oct; 98(4):934-40. doi: 10.3945/ajcn.113.064998. [PMID: 24004893]
  • Miki Terakata, Tsutomu Fukuwatari, Eri Kadota, Mitsue Sano, Masaaki Kanai, Toshikazu Nakamura, Hiroshi Funakoshi, Katsumi Shibata. The niacin required for optimum growth can be synthesized from L-tryptophan in growing mice lacking tryptophan-2,3-dioxygenase. The Journal of nutrition. 2013 Jul; 143(7):1046-51. doi: 10.3945/jn.113.176875. [PMID: 23700344]
  • D Theofylaktopoulou, Ø Midttun, A Ulvik, P M Ueland, G S Tell, S E Vollset, O Nygård, S J P M Eussen. A community-based study on determinants of circulating markers of cellular immune activation and kynurenines: the Hordaland Health Study. Clinical and experimental immunology. 2013 Jul; 173(1):121-30. doi: 10.1111/cei.12092. [PMID: 23607723]
  • Xiaoyan Gao, Mingxing Guo, Baosheng Zhao, Long Peng, Jiankun Su, Xu Bai, Jun Li, Yanjiang Qiao. A urinary metabonomics study on biochemical changes in yeast-induced pyrexia rats: a new approach to elucidating the biochemical basis of the febrile response. Chemico-biological interactions. 2013 Jun; 204(1):39-48. doi: 10.1016/j.cbi.2013.04.001. [PMID: 23583517]
  • Chi-Fen Chen, Tsan-Zon Liu, Wu-Hsiang Lan, Li-An Wu, Chin-Hung Tsai, Jeng-Fong Chiou, Li-Yu Tsai. Novel spectrophotometric method for the quantitation of urinary xanthurenic acid and its application in identifying individuals with hyperhomocysteinemia associated with Vitamin B₆ deficiency. BioMed research international. 2013; 2013(?):678476. doi: 10.1155/2013/678476. [PMID: 24151616]
  • S A G Lambrechts, A van Dam, J de Vos, A van Weert, T Sijen, M C G Aalders. On the autofluorescence of fingermarks. Forensic science international. 2012 Oct; 222(1-3):89-93. doi: 10.1016/j.forsciint.2012.05.004. [PMID: 22658744]
  • Roy M Nilsen, Anne-Lise Bjørke-Monsen, Oivind Midttun, Ottar Nygård, Eva R Pedersen, Arve Ulvik, Per Magnus, Håkon K Gjessing, Stein Emil Vollset, Per Magne Ueland. Maternal tryptophan and kynurenine pathway metabolites and risk of preeclampsia. Obstetrics and gynecology. 2012 Jun; 119(6):1243-50. doi: 10.1097/aog.0b013e318255004e. [PMID: 22617590]
  • Soumen K Manna, Andrew D Patterson, Qian Yang, Kristopher W Krausz, Jeffrey R Idle, Albert J Fornace, Frank J Gonzalez. UPLC-MS-based urine metabolomics reveals indole-3-lactic acid and phenyllactic acid as conserved biomarkers for alcohol-induced liver disease in the Ppara-null mouse model. Journal of proteome research. 2011 Sep; 10(9):4120-33. doi: 10.1021/pr200310s. [PMID: 21749142]
  • William R Wikoff, Megha A Nagle, Valentina L Kouznetsova, Igor F Tsigelny, Sanjay K Nigam. Untargeted metabolomics identifies enterobiome metabolites and putative uremic toxins as substrates of organic anion transporter 1 (Oat1). Journal of proteome research. 2011 Jun; 10(6):2842-51. doi: 10.1021/pr200093w. [PMID: 21476605]
  • Zhi-Heng Su, Shu-Qi Li, Guo-An Zou, Chang-Yuan Yu, Yan-Guo Sun, Hong-Wu Zhang, Ying Gu, Zhong-Mei Zou. Urinary metabonomics study of anti-depressive effect of Chaihu-Shu-Gan-San on an experimental model of depression induced by chronic variable stress in rats. Journal of pharmaceutical and biomedical analysis. 2011 Jun; 55(3):533-9. doi: 10.1016/j.jpba.2011.02.013. [PMID: 21398066]
  • Hee Jung Ahn, Kyung Wan Min, Youn-Ok Cho. Assessment of vitamin B(6) status in Korean patients with newly diagnosed type 2 diabetes. Nutrition research and practice. 2011 Feb; 5(1):34-9. doi: 10.4162/nrp.2011.5.1.34. [PMID: 21487494]
  • Don Otter, Mingshu Cao, Hui-Ming Lin, Karl Fraser, Shelley Edmunds, Geoff Lane, Daryl Rowan. Identification of urinary biomarkers of colon inflammation in IL10-/- mice using Short-Column LCMS metabolomics. Journal of biomedicine & biotechnology. 2011; 2011(?):974701. doi: 10.1155/2011/974701. [PMID: 21188174]
  • Shumin Liu, Fang Lu, Xijun Wang, Wenjun Sun, Pingping Chen, Wanru Dong. Metabolomic study of a rat fever model induced with 2,4-dinitrophenol and the therapeutic effects of a crude drug derived from Coptis chinensis. The American journal of Chinese medicine. 2011; 39(1):95-109. doi: 10.1142/s0192415x11008671. [PMID: 21213401]
  • Jessica A Bonzo, Andrew D Patterson, Kristopher W Krausz, Frank J Gonzalez. Metabolomics identifies novel Hnf1alpha-dependent physiological pathways in vivo. Molecular endocrinology (Baltimore, Md.). 2010 Dec; 24(12):2343-55. doi: 10.1210/me.2010-0130. [PMID: 20943816]
  • Colleen M McClean, Haydee Guerra Alvarado, Victor Neyra, Alejandro Llanos-Cuentas, Joseph M Vinetz. Optimized in vitro production of Plasmodium vivax ookinetes. The American journal of tropical medicine and hygiene. 2010 Dec; 83(6):1183-6. doi: 10.4269/ajtmh.2010.10-0195. [PMID: 21118919]
  • G O Obochi, O O E Amali, D O Ochalefu. Effect of melatonin and caffeine interaction on caffeine induced oxidative stress and sleep disorders. Nigerian journal of physiological sciences : official publication of the Physiological Society of Nigeria. 2010 Nov; 25(1):17-24. doi: NULL. [PMID: 22314898]
  • Hui-Ming Lin, Matthew P G Barnett, Nicole C Roy, Nigel I Joyce, Shuotun Zhu, Kelly Armstrong, Nuala A Helsby, Lynnette R Ferguson, Daryl D Rowan. Metabolomic analysis identifies inflammatory and noninflammatory metabolic effects of genetic modification in a mouse model of Crohn's disease. Journal of proteome research. 2010 Apr; 9(4):1965-75. doi: 10.1021/pr901130s. [PMID: 20141220]
  • Shuning Zheng, Mingyang Yu, Xiumei Lu, Taoguang Huo, Lin Ge, Jingyu Yang, Chunfu Wu, Famei Li. Urinary metabonomic study on biochemical changes in chronic unpredictable mild stress model of depression. Clinica chimica acta; international journal of clinical chemistry. 2010 Feb; 411(3-4):204-9. doi: 10.1016/j.cca.2009.11.003. [PMID: 19913000]
  • Abdulla A-B Badawy, Christopher J Morgan. Rapid Isocratic Liquid Chromatographic Separation and Quantification of Tryptophan and Six kynurenine Metabolites in Biological Samples with Ultraviolet and Fluorimetric Detection. International journal of tryptophan research : IJTR. 2010; 3(?):175-86. doi: 10.4137/ijtr.s6225. [PMID: 22084598]
  • Øivind Midttun, Steinar Hustad, Per M Ueland. Quantitative profiling of biomarkers related to B-vitamin status, tryptophan metabolism and inflammation in human plasma by liquid chromatography/tandem mass spectrometry. Rapid communications in mass spectrometry : RCM. 2009 May; 23(9):1371-9. doi: 10.1002/rcm.4013. [PMID: 19337982]
  • Hui-Ming Lin, Shelley I Edmunds, Nuala A Helsby, Lynnette R Ferguson, Daryl D Rowan. Nontargeted urinary metabolite profiling of a mouse model of Crohn's disease. Journal of proteome research. 2009 Apr; 8(4):2045-57. doi: 10.1021/pr800999t. [PMID: 19275240]
  • Wai Siang Law, Pei Yun Huang, Eng Shi Ong, Sunil Kumar Sethi, Sharon Saw, Choon Nam Ong, Sam Fong Yau Li. Combination of 1H nuclear magnetic resonance spectroscopy and liquid chromatography/mass spectrometry with pattern recognition techniques for evaluation of metabolic profile associated with albuminuria. Journal of proteome research. 2009 Apr; 8(4):1828-37. doi: 10.1021/pr800771f. [PMID: 19714874]
  • Milane S Leite, Rachel Thomaz, José Henrique M Oliveira, Pedro L Oliveira, José Roberto Meyer-Fernandes. Trypanosoma brucei brucei: effects of ferrous iron and heme on ecto-nucleoside triphosphate diphosphohydrolase activity. Experimental parasitology. 2009 Feb; 121(2):137-43. doi: 10.1016/j.exppara.2008.10.018. [PMID: 19027737]
  • Laddawan Senggunprai, Kouichi Yoshinari, Miki Shimada, Yasushi Yamazoe. Involvement of ST1B subfamily of cytosolic sulfotransferase in kynurenine metabolism to form natriuretic xanthurenic acid sulfate. The Journal of pharmacology and experimental therapeutics. 2008 Dec; 327(3):789-98. doi: 10.1124/jpet.108.143164. [PMID: 18815351]
  • Brian Crow, Michael Bishop, Ekaterina Paliakov, Dean Norton, Joe George, J Alexander Bralley. Analysis of urinary aromatic acids by liquid chromatography tandem mass spectrometry. Biomedical chromatography : BMC. 2008 Dec; 22(12):1346-53. doi: 10.1002/bmc.1064. [PMID: 18655225]
  • Maha Saeed, Will Roeffen, Neal Alexander, Christopher J Drakeley, Geoffrey A T Targett, Colin J Sutherland. Plasmodium falciparum antigens on the surface of the gametocyte-infected erythrocyte. PloS one. 2008 May; 3(5):e2280. doi: 10.1371/journal.pone.0002280. [PMID: 18509532]
  • Yousef A Taher, Benoit J A Piavaux, Reneé Gras, Betty C A M van Esch, Gerard A Hofman, Nanne Bloksma, Paul A J Henricks, Antoon J M van Oosterhout. Indoleamine 2,3-dioxygenase-dependent tryptophan metabolites contribute to tolerance induction during allergen immunotherapy in a mouse model. The Journal of allergy and clinical immunology. 2008 Apr; 121(4):983-91.e2. doi: 10.1016/j.jaci.2007.11.021. [PMID: 18179817]
  • Anaïs Merckx, Marie-Paule Nivez, Guillaume Bouyer, Pietro Alano, Gordon Langsley, Kirk Deitsch, Serge Thomas, Christian Doerig, Stéphane Egée. Plasmodium falciparum regulatory subunit of cAMP-dependent PKA and anion channel conductance. PLoS pathogens. 2008 Feb; 4(2):e19. doi: 10.1371/journal.ppat.0040019. [PMID: 18248092]
  • Christina D Moon, Xue-Xian Zhang, Sandra Matthijs, Mathias Schäfer, Herbert Budzikiewicz, Paul B Rainey. Genomic, genetic and structural analysis of pyoverdine-mediated iron acquisition in the plant growth-promoting bacterium Pseudomonas fluorescens SBW25. BMC microbiology. 2008 Jan; 8(?):7. doi: 10.1186/1471-2180-8-7. [PMID: 18194565]
  • Paddy Jim Baggot, Anna Jane Y Eliseo, Nathaniel G DeNicola, Jeremy A Kalamarides, James D Shoemaker. Pyridoxine-related metabolite concentrations in normal and Down syndrome amniotic fluid. Fetal diagnosis and therapy. 2008; 23(4):254-7. doi: 10.1159/000123610. [PMID: 18417989]
  • Christopher D Cain, Frank C Schroeder, Stewart W Shankel, Mark Mitchnick, Michael Schmertzler, Neal S Bricker. Identification of xanthurenic acid 8-O-beta-D-glucoside and xanthurenic acid 8-O-sulfate as human natriuretic hormones. Proceedings of the National Academy of Sciences of the United States of America. 2007 Nov; 104(45):17873-8. doi: 10.1073/pnas.0705553104. [PMID: 17978185]
  • Yueying Zhen, Kristopher W Krausz, Chi Chen, Jeffrey R Idle, Frank J Gonzalez. Metabolomic and genetic analysis of biomarkers for peroxisome proliferator-activated receptor alpha expression and activation. Molecular endocrinology (Baltimore, Md.). 2007 Sep; 21(9):2136-51. doi: 10.1210/me.2007-0150. [PMID: 17550978]
  • A Maxwell Burroughs, S Balaji, Lakshminarayan M Iyer, L Aravind. Small but versatile: the extraordinary functional and structural diversity of the beta-grasp fold. Biology direct. 2007 Jul; 2(?):18. doi: 10.1186/1745-6150-2-18. [PMID: 17605815]
  • Tsutomu Fukuwatari, Katsumi Shibata. Effect of nicotinamide administration on the tryptophan-nicotinamide pathway in humans. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition. 2007 Jul; 77(4):255-62. doi: 10.1024/0300-9831.77.4.255. [PMID: 18271280]
  • M Christensen, M Duno, A M Lund, F Skovby, E Christensen. Xanthurenic aciduria due to a mutation in KYNU encoding kynureninase. Journal of inherited metabolic disease. 2007 Apr; 30(2):248-55. doi: 10.1007/s10545-007-0396-2. [PMID: 17334708]
  • Jiangshan Wang, Xinjie Zhao, Yufang Zheng, Hongwei Kong, Guo Lu, Zongwei Cai, Guowang Xu. [Metabolite fingerprint and biomarkers identification of rat urine after dosed with ginsenoside Rg3 based on ultra high performance liquid chromatography/time-of-flight mass spectrometry (UPLC/TOF-MS)]. Se pu = Chinese journal of chromatography. 2006 Jan; 24(1):5-9. doi: NULL. [PMID: 16827300]
  • Andrew Bahn, Marija Ljubojevic, Heiko Lorenz, Christian Schultz, Estifanos Ghebremedhin, Bernhard Ugele, Ivan Sabolic, Gerhard Burckhardt, Yohannes Hagos. Murine renal organic anion transporters mOAT1 and mOAT3 facilitate the transport of neuroactive tryptophan metabolites. American journal of physiology. Cell physiology. 2005 Nov; 289(5):C1075-84. doi: 10.1152/ajpcell.00619.2004. [PMID: 15944205]
  • E M Lenz, J Bright, R Knight, F R Westwood, D Davies, H Major, I D Wilson. Metabonomics with 1H-NMR spectroscopy and liquid chromatography-mass spectrometry applied to the investigation of metabolic changes caused by gentamicin-induced nephrotoxicity in the rat. Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals. 2005 Mar; 10(2-3):173-87. doi: 10.1080/13547500500094034. [PMID: 16076731]
  • R E Williams, H Major, E A Lock, E M Lenz, I D Wilson. D-Serine-induced nephrotoxicity: a HPLC-TOF/MS-based metabonomics approach. Toxicology. 2005 Feb; 207(2):179-90. doi: 10.1016/j.tox.2004.08.023. [PMID: 15596249]
  • Wei Wang, Bin Qiu, Xueqin Xu, Lan Zhang, Guonan Chen. Separation and determination of L-tryptophan and its metabolites by capillary micellar electrokinetic chromatography with amperometric detection. Electrophoresis. 2005 Feb; 26(4-5):903-910. doi: 10.1002/elps.200406099. [PMID: 15714546]
  • En-Pei I Chiang, Jacob Selhub, Pamela J Bagley, Gerard Dallal, Ronenn Roubenoff. Pyridoxine supplementation corrects vitamin B6 deficiency but does not improve inflammation in patients with rheumatoid arthritis. Arthritis research & therapy. 2005; 7(6):R1404-11. doi: 10.1186/ar1839. [PMID: 16277693]
  • E M Lenz, J Bright, R Knight, I D Wilson, H Major. A metabonomic investigation of the biochemical effects of mercuric chloride in the rat using 1H NMR and HPLC-TOF/MS: time dependent changes in the urinary profile of endogenous metabolites as a result of nephrotoxicity. The Analyst. 2004 Jun; 129(6):535-41. doi: 10.1039/b400159c. [PMID: 15152332]
  • E M Lenz, J Bright, R Knight, I D Wilson, H Major. Cyclosporin A-induced changes in endogenous metabolites in rat urine: a metabonomic investigation using high field 1H NMR spectroscopy, HPLC-TOF/MS and chemometrics. Journal of pharmaceutical and biomedical analysis. 2004 May; 35(3):599-608. doi: 10.1016/j.jpba.2004.02.013. [PMID: 15137985]
  • Oliver Billker, Sandrine Dechamps, Rita Tewari, Gerald Wenig, Blandine Franke-Fayard, Volker Brinkmann. Calcium and a calcium-dependent protein kinase regulate gamete formation and mosquito transmission in a malaria parasite. Cell. 2004 May; 117(4):503-14. doi: 10.1016/s0092-8674(04)00449-0. [PMID: 15137943]
  • Kenneth D Vernick. Gamete interruptus; a novel calcium-dependent kinase is essential for malaria sexual reproduction. Cell. 2004 May; 117(4):419-20. doi: 10.1016/s0092-8674(04)00455-6. [PMID: 15137935]
  • Caroline M Forrest, Alan Kennedy, Trevor W Stone, Nicholas Stoy, L Gail Darlington. Kynurenine and neopterin levels in patients with rheumatoid arthritis and osteoporosis during drug treatment. Advances in experimental medicine and biology. 2003; 527(?):287-95. doi: 10.1007/978-1-4615-0135-0_32. [PMID: 15206742]
  • Katsumi Shibata, Tsutomu Fukuwatari, Mayumi Murakami, Ryuzo Sasaki. Increase in conversion of tryptophan to niacin in pregnant rats. Advances in experimental medicine and biology. 2003; 527(?):435-41. doi: 10.1007/978-1-4615-0135-0_51. [PMID: 15206761]
  • Tsutomu Fukuwatari, Seiko Ohsaki, Yuko Suzuki, Sin-ichi Fukuoka, Ryuzo Sasaki, Katsumi Shibata. The effects of phthalate esters on the tryptophan-niacin metabolism. Advances in experimental medicine and biology. 2003; 527(?):659-64. doi: 10.1007/978-1-4615-0135-0_77. [PMID: 15206787]
  • Caroline M Forrest, Stuart R Gould, L Gail Darlington, Trevor W Stone. Levels of purine, kynurenine and lipid peroxidation products in patients with inflammatory bowel disease. Advances in experimental medicine and biology. 2003; 527(?):395-400. doi: 10.1007/978-1-4615-0135-0_46. [PMID: 15206756]
  • Natalia V Melnikova. Neurokynurenines--seizures or/and anxiety in children with epilepsy?. Advances in experimental medicine and biology. 2003; 527(?):191-5. doi: 10.1007/978-1-4615-0135-0_22. [PMID: 15206732]
  • Tsutomu Fukuwatari, Etsuro Sugimoto, Katsumi Shibata. Growth-promoting activity of pyrazinoic acid, a putative active compound of antituberculosis drug pyrazinamide, in niacin-deficient rats through the inhibition of ACMSD activity. Bioscience, biotechnology, and biochemistry. 2002 Jul; 66(7):1435-41. doi: 10.1271/bbb.66.1435. [PMID: 12224625]
  • D Pawlak, A Tankiewicz, P Mysliwiec, W Buczko. Tryptophan metabolism via the kynurenine pathway in experimental chronic renal failure. Nephron. 2002 Mar; 90(3):328-35. doi: 10.1159/000049069. [PMID: 11867954]
  • D Pawlak, A Tankiewicz, W Buczko. Kynurenine and its metabolites in the rat with experimental renal insufficiency. Journal of physiology and pharmacology : an official journal of the Polish Physiological Society. 2001 Dec; 52(4 Pt 2):755-66. doi: NULL. [PMID: 11785771]
  • T Fukuwatari, Y Morikawa, F Hayakawa, E Sugimoto, K Shibata. Influence of adenine-induced renal failure on tryptophan-niacin metabolism in rats. Bioscience, biotechnology, and biochemistry. 2001 Oct; 65(10):2154-61. doi: 10.1271/bbb.65.2154. [PMID: 11758903]
  • J Seifert. Toxicologic significance of the hyperglycemia caused by organophosphorous insecticides. Bulletin of environmental contamination and toxicology. 2001 Oct; 67(4):463-9. doi: 10.1007/s001280146. [PMID: 11779058]
  • K Murakami, M Ito, M Yoshino. Xanthurenic acid inhibits metal ion-induced lipid peroxidation and protects NADP-isocitrate dehydrogenase from oxidative inactivation. Journal of nutritional science and vitaminology. 2001 Aug; 47(4):306-10. doi: 10.3177/jnsv.47.306. [PMID: 11767212]
  • T Fukuwatari, E Sugimoto, K Shibata. [Effect of feeding with a poisonous mushroom Clitocybe acromelalga on the metabolism of tryptophan-niacin in rats]. Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan. 2001 Jun; 42(3):190-6. doi: 10.3358/shokueishi.42.190. [PMID: 11577392]
  • K Shibata, T Fukuwatari, E Sugimoto. Effects of dietary pyrazinamide, an antituberculosis agent, on the metabolism of tryptophan to niacin and of tryptophan to serotonin in rats. Bioscience, biotechnology, and biochemistry. 2001 Jun; 65(6):1339-46. doi: 10.1271/bbb.65.1339. [PMID: 11471733]
  • J J Matte, C L Girard, B Sève. Effects of long-term parenteral administration of vitamin B6 on B6 status and some aspects of the glucose and protein metabolism of early-weaned piglets. The British journal of nutrition. 2001 Jan; 85(1):11-21. doi: 10.1079/bjn2000221. [PMID: 11227029]
  • H Z Malina, C Richter, M Mehl, O M Hess. Pathological apoptosis by xanthurenic acid, a tryptophan metabolite: activation of cell caspases but not cytoskeleton breakdown. BMC physiology. 2001; 1(?):7. doi: 10.1186/1472-6793-1-7. [PMID: 11459518]
  • D Pawlak, K Pawlak, J Malyszko, M Mysliwiec, W Buczko. Accumulation of toxic products degradation of kynurenine in hemodialyzed patients. International urology and nephrology. 2001; 33(2):399-404. doi: 10.1023/a:1015238418500. [PMID: 12092667]
  • T Hayakawa, Y Iida, H Tsuge. Konjac mannan improves the vitamin B-6 status of rats fed a vitamin B-6-deficient diet. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition. 1999 Mar; 69(2):106-12. doi: 10.1024/0300-9831.69.2.106. [PMID: 10218147]
  • K Goda, Y Hamane, R Kishimoto, Y Ogishi. Radical scavenging properties of tryptophan metabolites. Estimation of their radical reactivity. Advances in experimental medicine and biology. 1999; 467(?):397-402. doi: 10.1007/978-1-4615-4709-9_50. [PMID: 10721081]
  • K Shibata, T Kondo, A Miki. Increased conversion ratio of tryptophan to niacin in severe food restriction. Bioscience, biotechnology, and biochemistry. 1998 Mar; 62(3):580-3. doi: 10.1271/bbb.62.580. [PMID: 9571792]
  • A Muñóz-Hoyos, A Molina-Carballo, T Rodríguez-Cabezas, J Uberos-Fernández, C Ruiz-Cosano, D Acuña-Castroviejo. Relationships between methoxyindole and kynurenine pathway metabolites in plasma and urine in children suffering from febrile and epileptic seizures. Clinical endocrinology. 1997 Dec; 47(6):667-77. doi: 10.1046/j.1365-2265.1997.2991136.x. [PMID: 9497873]
  • M Maeno, Y Morimoto, T Hayakawa, Y Suzuki, H Tsuge. Feeding experiments of pyridoxine derivatives as vitamin B6. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition. 1997; 67(6):444-9. doi: . [PMID: 9433679]