Representative LC/UV chromatogram under typical analytical conditions (C18 column; mobile phase: 5–100% ACN / H2O (0.05% H3PO4), linear gradient 20 min; flow rate: 0.2 mL/min; detection: 210 nm).
NMR Spectral Data
Representative 1H NMR (500 MHz) spectrum confirming the structure of Quinolactacin A. Representative 13C NMR (125 MHz) spectrum supporting structural assignment of Quinolactacin A.
Source Organism
Penicillium citrinum.
Summary
Quinolactacin A is a fungal 4-quinolone metabolite that inhibits TNF production.
Details
Quinolactacin A is a secondary metabolite produced by Penicillium species and structurally classified as an N-methyl-4-quinolone conjugated with a γ-lactam moiety. It was originally identified as a potent inhibitor of tumor necrosis factor (TNF)-α production in lipopolysaccharide-stimulated murine macrophages. Isotope-labeling studies clarified its biosynthetic origin from acetate, anthranilate, isoleucine, and methionine precursors. Subsequent heterologous expression and enzymatic reconstitution revealed a concise nonribosomal peptide synthetase (NRPS)-dependent pathway responsible for quinolactacin assembly.