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

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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.

Original languageEnglish
Pages (from-to)2631-2643
Number of pages13
JournalBeilstein Journal of Organic Chemistry
Volume15
DOIs
Publication statusPublished - 5 Nov 2019

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Bibliographical note

Copyright the Author(s) 2019. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

Keywords

  • Aspergillus
  • Biosynthesis
  • Drimane
  • Secondary metabolites
  • Sesquiterpenoid
  • Terpenes

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