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}}</ref><ref name="pmid9575140">{{cite journal |last1=Garcia |first1=GE |last2=Wirtz |first2=RA |last3=Barr |first3=JR |last4=Woolfitt |first4=A |last5=Rosenberg |first5=R |title=Xanthurenic acid induces gametogenesis in Plasmodium, the malaria parasite. |journal=The Journal of Biological Chemistry |date=May 15, 1998 |volume=273 |issue=20 |pages=12003–5 |pmid=9575140 |url=http://www.jbc.org/content/273/20/12003.full |doi=10.1074/jbc.273.20.12003}}</ref> It is found in the gut of the ''[[Anopheles]]'' mosquito.
}}</ref><ref name="pmid9575140">{{cite journal |last1=Garcia |first1=GE |last2=Wirtz |first2=RA |last3=Barr |first3=JR |last4=Woolfitt |first4=A |last5=Rosenberg |first5=R |title=Xanthurenic acid induces gametogenesis in Plasmodium, the malaria parasite. |journal=The Journal of Biological Chemistry |date=May 15, 1998 |volume=273 |issue=20 |pages=12003–5 |pmid=9575140 |url=http://www.jbc.org/content/273/20/12003.full |doi=10.1074/jbc.273.20.12003}}</ref> It is found in the gut of the ''[[Anopheles]]'' mosquito.


Xanthurenic acid is a metabolic intermediate that accumulates and is excreted by [[pyridoxine]] (vitamin B<sub>6</sub>) deficient animals after the ingestion of [[tryptophan]].<ref name="Merck"/><ref>[http://www.sigmaaldrich.com/catalog/search/ProductDetail/FLUKA/95570 Xanthurenic acid] at [[Sigma-Aldrich]]</ref>
Xanthurenic acid is a metabolic intermediate that accumulates and is excreted by [[pyridoxine]] (vitamin B<sub>6</sub>) deficient animals after the ingestion of [[tryptophan]].<ref name="Merck"/><ref>[http://www.sigmaaldrich.com/catalog/search/ProductDetail/FLUKA/95570 Xanthurenic acid]{{dead link|date=July 2016 |bot=InternetArchiveBot |fix-attempted=yes }} at [[Sigma-Aldrich]]</ref>


Xanthurenic acid is suspected to be an [[endogenous]] [[agonist]] for Group II [[metabotropic glutamate receptors]] in humans.<ref>{{cite journal |last1=Copeland |first1=C. S. |last2=Neale |first2=S. A. |last3=Salt |first3=T. E. |title=Actions of Xanthurenic Acid, a putative endogenous Group II metabotropic glutamate receptor agonist, on sensory transmission in the thalamus |doi=10.1016/j.neuropharm.2012.03.009 |journal=Neuropharmacology |volume=66 |pages=133–142 |year=2013 |pmid=22491023 |pmc=}}</ref> It is also known to be a potent [[VGLUT]] inhibitor, thereby preventing the movement of [[glutamate]] from the cytoplasm into [[synaptic vesicle]]s, an action that it mediates via [[competitive antagonist|competitive blockade]] of [[vesicular glutamate transporter]]s (K<sub>i</sub> = 0.19 mM).<ref name="pmid9776380">{{cite journal |vauthors=Bartlett RD, Esslinger CS, Thompson CM, Bridges RJ |title=Substituted quinolines as inhibitors of L-glutamate transport into synaptic vesicles |journal=Neuropharmacology |volume=37 |issue=7 |pages=839–46 |year=1998 |pmid=9776380 |doi=10.1016/s0028-3908(98)00080-x |url=}}</ref>
Xanthurenic acid is suspected to be an [[endogenous]] [[agonist]] for Group II [[metabotropic glutamate receptors]] in humans.<ref>{{cite journal |last1=Copeland |first1=C. S. |last2=Neale |first2=S. A. |last3=Salt |first3=T. E. |title=Actions of Xanthurenic Acid, a putative endogenous Group II metabotropic glutamate receptor agonist, on sensory transmission in the thalamus |doi=10.1016/j.neuropharm.2012.03.009 |journal=Neuropharmacology |volume=66 |pages=133–142 |year=2013 |pmid=22491023 |pmc=}}</ref> It is also known to be a potent [[VGLUT]] inhibitor, thereby preventing the movement of [[glutamate]] from the cytoplasm into [[synaptic vesicle]]s, an action that it mediates via [[competitive antagonist|competitive blockade]] of [[vesicular glutamate transporter]]s (K<sub>i</sub> = 0.19 mM).<ref name="pmid9776380">{{cite journal |vauthors=Bartlett RD, Esslinger CS, Thompson CM, Bridges RJ |title=Substituted quinolines as inhibitors of L-glutamate transport into synaptic vesicles |journal=Neuropharmacology |volume=37 |issue=7 |pages=839–46 |year=1998 |pmid=9776380 |doi=10.1016/s0028-3908(98)00080-x |url=}}</ref>

Revision as of 16:23, 16 July 2016

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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.000.373 Edit this at Wikidata
EC Number
  • 200-410-1
KEGG
  • 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) ☒N
    Key: FBZONXHGGPHHIY-UHFFFAOYSA-N ☒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
  • OC2=CC(C(O)=O)=NC1=C(O)C=CC=C12
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).
☒N verify (what is checkY☒N ?)

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 (Ki = 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

References

  1. ^ a b 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.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  4. ^ Xanthurenic acid[permanent dead link] 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.
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