Discovery of brevijanazines from Aspergillus brevijanus reveals the molecular basis for p-nitrobenzoic acid in fungi?
Hang Li , Paul M. Mirzayans , Mark S. Butler , Alastair E. Lacey , Daniel Vuong , Rachel Chen , John A. Kalaitzis , Stephen A. Moggach , Ernest Lacey , Andrew M. Piggott , Yit-Heng Chooi
Abstract
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.