2-Nonylquinolin-4(1H)-one is a quinolone alkaloid that has been found in P. aeruginosa and has diverse biological activities.1,2,3,4 It reduces infection of Huh7.5 cells by hepatitis C virus (HCV) with an IC50 value of 1.4 µg/ml.1 2-Nonylquinolin-4(1H)-one (50 and 100 µg/ml) is also active against L. gongylophorus, a symbiotic fungus of the agricultural pest A. sexdens (leaf-cutting ant).2 It inhibits activation of nuclear factor of activated T cells (NFAT) induced by phorbol 12-myristate 13-acetate and the calcium ionophore A23187 in Jurkat cells (IC50 = 3.44 µM), but not LPS-induced NF-κB activation in RAW 264.7 cells (IC50 = >100 µM), in reporter assays.3 This compound is expected to exist in one or both tautomeric forms, depending on experimental conditions.
1.Wahyuni, T.S., Widyawaruyanti, A., Lusida, M.I., et al.Inhibition of hepatitis C virus replication by chalepin and pseudane IX isolated from Ruta angustifolia leavesFitoterapia99276-283(2014) 2.Biavatti, M.W., Vieira, P.C., da Silva, F.d.G.F., et al.Biological activity of quinoline alkaloids from Raulinoa echinata and x-ray structure of flindersiamineJ. Braz. Chem. Soc.13(1)66-70(2002) 3.Jin, H.Z., Lee, J.H., Lee, D., et al.Quinolone alkaloids with inhibitory activity against nuclear factor of activated T cells from the fruits of Evodia rutaecarpaBiol. Pharm. Bull.27(6)926-928(2004) 4.Ortori, C.A., Dubern, J.-F., Chhabra, S.R., et al.Simultaneous quantitative profiling of N-acyl-L-homoserine lactone and 2-alkyl-4(1H)-quinolone families of quorum-sensing signaling molecules using LC-MS/MSAnal. Bioanal. Chem.399(2)839-850(2011)