Xanthurenic acid, or xanthurenate, is a metabolic intermediate that accumulates and is excreted by pyridoxine (vitamin B6) deficient animals after the ingestion of tryptophan.[1][2]
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| Names | |
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| Preferred IUPAC name
4,8-Dihydroxyquinoline-2-carboxylic acid | |
| Other names
Xanthuric acid
Xanthurenate 8-Hydroxykynurenic acid 4,8-Dihydroxyquinaldic acid | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.000.373 |
| EC Number |
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| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C10H7NO4 | |
| Molar mass | 205.169 g·mol−1 |
| Appearance | Yellow crystals |
| Melting point | 286 °C (547 °F; 559 K) |
| Insoluble | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Xanthurenic acid is suspected to be an endogenous agonist for Group II metabotropic glutamate receptors in humans.[3] It is also known to be a potent VGLUT inhibitor, thereby preventing the movement of glutamate from the cytoplasm into synaptic vesicles, an action that it mediates via competitive blockade of vesicular glutamate transporters (Ki = 0.19 mM).[4]
In 2015[update] researchers reported a marked reduction of xanthurenic acid levels in the serum of patients with schizophrenia.[5] A recent meta-analysis showed that blood xanthurenic acid levels are lower in individuals suffering from bipolar disorder as well.[6]
Xanthurenic acid has also been shown to induce gametogenesis of Plasmodium falciparum, the parasite that causes malaria.[7][8] It is found in the gut of the Anopheles mosquito.
See also
editReferences
edit- ^ a b Merck Index, 11th Edition, 9977.
- ^ Xanthurenic acid at Sigma-Aldrich
- ^ Copeland, C. S.; Neale, S. A.; Salt, T. E. (2013). "Actions of Xanthurenic Acid, a putative endogenous Group II metabotropic glutamate receptor agonist, on sensory transmission in the thalamus". Neuropharmacology. 66: 133–142. doi:10.1016/j.neuropharm.2012.03.009. PMID 22491023. S2CID 37921378.
- ^ Bartlett RD, Esslinger CS, Thompson CM, Bridges RJ (1998). "Substituted quinolines as inhibitors of L-glutamate transport into synaptic vesicles". Neuropharmacology. 37 (7): 839–46. doi:10.1016/s0028-3908(98)00080-x. PMID 9776380. S2CID 39853026.
- ^ Fazio, F.; Lionetto, L.; Curto, M. (2015). "Xanthurenic Acid Activates mGlu2/3 Metabotropic Glutamate Receptors and is a Potential Trait Marker for Schizophrenia". Scientific Reports. 5: 17799. Bibcode:2015NatSR...517799F. doi:10.1038/srep17799. PMC 4672300. PMID 26643205.
- ^ Bartoli, F; Misiak, B; Callovini, T; Cavaleri, D; Cioni, RM; Crocamo, C; Savitz, JB; Carrà, G (19 October 2020). "The kynurenine pathway in bipolar disorder: a meta-analysis on the peripheral blood levels of tryptophan and related metabolites". Molecular Psychiatry. 26 (7): 3419–3429. doi:10.1038/s41380-020-00913-1. PMID 33077852. S2CID 224314102.
- ^ Billker, O; Lindo, V; Panico, M; Etienne, AE; Paxton, T; Dell, A; Rogers, M; Sinden, RE; Morris, HR (March 19, 1998). "Identification of xanthurenic acid as the putative inducer of malaria development in the mosquito". Nature. 392 (6673): 289–292. Bibcode:1998Natur.392..289B. doi:10.1038/32667. PMID 9521324. S2CID 2584314.
- ^ Garcia, GE; Wirtz, RA; Barr, JR; Woolfitt, A; Rosenberg, R (May 15, 1998). "Xanthurenic acid induces gametogenesis in Plasmodium, the malaria parasite". The Journal of Biological Chemistry. 273 (20): 12003–5. doi:10.1074/jbc.273.20.12003. PMID 9575140.