Xanthurenic acid

Xanthurenic acid^[1]

Names
IUPAC name 8-Hydroxy-4-oxo-1H-quinoline-2-carboxylic acid
Other names Xanthuric acid Xanthurenate 8-Hydroxykynurenic acid 4,8-Dihydroxyquinaldic acid
Identifiers
CAS Number	59-00-7
3D model (Jmol)	Interactive image
ChEBI	CHEBI:10072
ChemSpider	5497
ECHA InfoCard	100.000.373
EC Number	200-410-1
KEGG	C02470
PubChem	5699
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) Key: FBZONXHGGPHHIY-UHFFFAOYSA-N InChI=1/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) Key: FBZONXHGGPHHIY-UHFFFAOYAE
SMILES OC2=CC(C(O)=O)=NC1=C(O)C=CC=C12
Properties
Chemical formula	C10H7NO4
Molar mass	205.17 g·mol^−1
Appearance	Yellow crystals
Melting point	286 °C (547 °F; 559 K)
Solubility in water	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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Infobox references

Xanthurenic acid, or xanthurenate, is a chemical shown to induce gametogenesis of Plasmodium falciparum, the parasite that causes malaria.^[2][3] It is found in the gut of the Anopheles mosquito.

Xanthurenic acid is a metabolic intermediate that accumulates and is excreted by pyridoxine (vitamin B₆) deficient animals after the ingestion of tryptophan.^[1][4]

Xanthurenic acid is suspected to be an endogenous agonist for Group II metabotropic glutamate receptors in humans.^[5] 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 (K_i = 0.19 mM).^[6] In 2015 researchers reported a marked reduction of xanthurenic acid levels in the serum of patients with schizophrenia, describing this phenomenon as a potential trait marker for schizophrenia.^[7]

See also

• Kynurenic acid
• 7-Chlorokynurenic acid

References

1. Merck Index, 11th Edition, 9977.
2. 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. doi:10.1038/32667. PMID 9521324.
3. 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.
4. Xanthurenic acid at Sigma-Aldrich
5. 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.
6. 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.
7. 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. doi:10.1038/srep17799. PMC 4672300. PMID 26643205.