Description
Cinnabarinic acid is a phenoxazinone produced by the oxidative dimerization of 3-
hydroxyanthranilic acid (3-
HAA) as part of the metabolism of tryptophan in the kynurenic pathway. It acts as a partial receptor agonist of the metabotropic glutamate receptor 4 (mGlu4), effective at 100 μM, with no activity at other mGlu receptor subtypes. 3-
HAA does not affect mGlu receptors, including mGlu4. Cinnabarinic acid induces apoptosis of T cells at 300-
500 μM, a potency some ten times that of 3-
HAA.
Chemical Properties
Dark Red Solid
Uses
Cinnabarinic acid may be used in studies of the functions of components of the kynurenine metabolic pathway. It may be used to study it role as a metabotropic glutamate receptor (mGlu4R-specific) agonist.
Uses
A natural phenoxazinone deriv
Cin
nabarinic acid strongly induces apoptosis in thymocytes through the generation of reactive oxygen species and the induction of caspase.
Uses
A natural phenoxazinone derivative, Cinnabarinic acid is obtained in vitro with aid of laccase by oxidative dimerization of 3-Hydroxyanthranilic acid (a metabolite of the amino acid Trytophan). Cinnabarinic acid strongly induces apoptosis in thymocytes through the generation of reactive oxygen species and the induction of caspase.
Definition
ChEBI: Cinnavalininate is a phenoxazine.
Biochem/physiol Actions
Cinnabarinic acid is a kynurenine pathway metabolite of tryptophan, produced by the oxidation of 3-Hydroxyanthranilic acid. Cinnabarinic acid leads to loss of mitochondrial respiration and apoptosis, and has also been shown to be an mGlu4R-specific agonist.
References
[1] MARGARET M LOWE. Identification of cinnabarinic acid as a novel endogenous aryl hydrocarbon receptor ligand that drives IL-22 production.[J]. ACS Applied Bio Materials, 2014: e87877. DOI:
10.1371/journal.pone.0087877[2] RIE HIRAMATSU. Cinnabarinic acid generated from 3-hydroxyanthranilic acid strongly induces apoptosis in thymocytes through the generation of reactive oxygen species and the induction of caspase[J]. Journal of cellular biochemistry, 2007, 103 1: 42-53. DOI:
10.1002/jcb.21384[3] F FAZIO. Cinnabarinic acid, an endogenous metabolite of the kynurenine pathway, activates type 4 metabotropic glutamate receptors.[J]. Molecular Pharmacology, 2012, 81 5: 643-656. DOI:
10.1124/mol.111.074765
