Definition
ChEBI: N-oleoyl-L-glutamine is an L-glutamine derivative resulting from the formal condensation of the carboxy group of oleic acid with the amino group of L-glutamine. It is a L-glutamine derivative and a N-(fatty acyl)-L-alpha-amino acid. It is functionally related to an oleic acid. It is a conjugate acid of a N-oleoyl-L-glutaminate.
Biological Activity
N-Oleoyl glutamine is an endogenous N-acyl amine.1,2 It is both formed and degraded by peptidase M20 domain-containing 1 (PM20D1), a factor secreted by thermogenic adipose cells. N-Oleoyl glutamine (50 μM) induces mitochondrial uncoupling to increase respiration in C2C12 cells by 64%.3 It inhibits capsaicin-induced calcium flux in HEK293A cells co-transfected with transient receptor potential vanilloid 1 (TRPV1) and red fluorescent protein (RFP).2 N-Oleoyl glutamine (100 mg/kg) reduces the number of acetic acid-induced abdominal constrictions, as well as formalin-induced paw licking in mice.
References
1.Long, J.Z., Svensson, K.J., Bateman, L.A., et al.The secreted enzyme PM20D1 regulates lipidated amino acid uncouplers of mitochondriaCell166(2)1-12(2016)
2.Long, J.Z., Roche, A.M., Berdan, C.A., et al.Ablation of PM20D1 reveals N-acyl amino acid control of metabolism and nociceptionProc. Natl. Acad. Sci. U.S.A.115(29)E6937-E6945(2018)
3.Lin, H., Long, J.Z., Roche, A.M., et al.Discovery of hydrolysis-resistant isoindoline N-acyl amino acid analogues that stimulate mitochondrial respirationJ. Med. Chem.61(7)3224-3230(2018)
