Discovery of brevijanazines from reveals the molecular basis for -nitrobenzoic acid in fungi

The brevijanazines are novel p -nitrobenzoylated piperazines isolated from Aspergillus brevijanus . Their structures were elucidated by spectroscopic analysis, X-ray crystallography and total synthesis. Heterologous biosynthesis, precursor feeding and in vitro microsomal assays unveiled the biosynthetic pathway to the brevijanazines, featuring a cytochrome P450 oxygenase that converts p -aminobenzoic acid to p -nitrobenzoic acid. The discovery of a novel family of p -nitrobenzoylated piperazines from Aspergillus brevijanus revealed that the biosynthesis of p -nitrobenzoic acid in fungi is catalysed by a PABA synthase, an aminodeoxychorismate synthase and a cytochrome P450.