2-Nonylquinolin-4(1H)-one (Synonyms: 2-n-Nonyl-4-quinolone, 2-Nonyl-1H-quinolin-4-one, 2-Nonylquinolin-4(1H)-one, Pseudane IX)

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)