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.
Heather J Lacey  1  2 ,  Cameron L M Gilchrist  3 ,  Andrew Crombie  1 ,  John A Kalaitzis  1  4 ,  Daniel Vuong  1 ,  Peter J Rutledge  2 ,  Peter Turner  2 ,  John I Pitt  1 ,  Ernest Lacey  1  4 ,  Yit-Heng Chooi  3 ,  Andrew M Piggott  4
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.
PMID: 31807198 DOI: 10.3762/bjoc.15.256
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.
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