Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis

Heather J Lacey; Cameron L M Gilchrist; Andrew Crombie; John A Kalaitzis; Daniel Vuong; Peter J Rutledge; Peter Turner; John I Pitt; Ernest Lacey; Yit-Heng Chooi; Andrew M Piggott

doi:10.3762/bjoc.15.256

Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis

Beilstein J Org Chem. 2019 Nov 5:15:2631-2643. doi: 10.3762/bjoc.15.256. eCollection 2019.

Authors

Heather J Lacey^{1

2}, Cameron L M Gilchrist³, Andrew Crombie¹, John A Kalaitzis^{1

4}, Daniel Vuong¹, Peter J Rutledge², Peter Turner², John I Pitt¹, Ernest Lacey^{1

4}, Yit-Heng Chooi³, Andrew M Piggott⁴

Affiliations

¹ Microbial Screening Technologies, Smithfield, NSW 2164, Australia.
² School of Chemistry, The University of Sydney, NSW 2006, Australia.
³ School of Molecular Sciences, The University of Western Australia, WA 6009, Australia.
⁴ Department of Molecular Sciences, Macquarie University, NSW 2109, Australia.

Abstract

Chemical investigation of an undescribed Australian fungus, Aspergillus nanangensis, led to the identification of the nanangenines - a family of seven new and three previously reported drimane sesquiterpenoids. The structures of the nanangenines were elucidated by detailed spectroscopic analysis supported by single crystal X-ray diffraction studies. The compounds were assayed for in vitro activity against bacteria, fungi, mammalian cells and plants. Bioinformatics analysis, including comparative analysis with other acyl drimenol-producing Aspergilli, led to the identification of a putative nanangenine biosynthetic gene cluster that corresponds to the proposed biosynthetic pathway for nanangenines.

Keywords: Aspergillus; biosynthesis; drimane; secondary metabolites; sesquiterpenoid; terpenes.