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

doi:10.1039/D2CC01679F

Discovery of brevijanazines from Aspergillus brevijanus reveals the molecular basis for p-nitrobenzoic acid in fungi†

Hang Li,

*^ab Paul M. Mirzayans,^c Mark S. Butler,

^d Alastair E. Lacey,^e Daniel Vuong,

^e Rachel Chen,^e John A. Kalaitzis,

^ce Stephen A. Moggach,

^bf Ernest Lacey,

^ce Andrew M. Piggott

*^c and Yit-Heng Chooi

*^b

Author affiliations

* Corresponding authors

^a School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong 510006, China
E-mail: lihang33@mail.sysu.edu.cn

^b School of Molecular Sciences, The University of Western Australia, Perth, WA 6009, Australia
E-mail: yitheng.chooi@uwa.edu.au

^c School of Natural Sciences, Macquarie University, Sydney, NSW 2109, Australia
E-mail: andrew.piggott@mq.edu.au

^d MSBChem Consulting, New Farm, QLD 4005, Australia

^e Microbial Screening Technologies Pty. Ltd., Smithfield, NSW 2164, Australia

^f Centre for Microscopy, Characterisation and Analysis, The University of Western Australia, Perth, WA 6009, Australia

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.

This article is part of the themed collection: Chemical Communications HOT Articles 2022

Chemical Communications

Discovery of brevijanazines from Aspergillus brevijanus reveals the molecular basis for p-nitrobenzoic acid in fungi†

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

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