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

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

Department of Molecular Sciences

Research output: Contribution to journal › Article

1 Citation (Scopus)

2 Downloads (Pure)

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 language	English
Pages (from-to)	2631-2643
Number of pages	13
Journal	Beilstein Journal of Organic Chemistry
Volume	15
DOIs	https://doi.org/10.3762/bjoc.15.256
Publication status	Published - 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

Cite this

Lacey, H. J., Gilchrist, C. L. M., Crombie, A., Kalaitzis, J. A., Vuong, D., Rutledge, P. J., ... Piggott, A. M. (2019). Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis. Beilstein Journal of Organic Chemistry, 15, 2631-2643. https://doi.org/10.3762/bjoc.15.256

Lacey, Heather J. ; Gilchrist, Cameron L. M. ; Crombie, Andrew ; Kalaitzis, John A. ; Vuong, Daniel ; Rutledge, Peter J. ; Turner, Peter ; Pitt, John I. ; Lacey, Ernest ; Chooi, Yit-Heng ; Piggott, Andrew M. / Nanangenines : drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis. In: Beilstein Journal of Organic Chemistry. 2019 ; Vol. 15. pp. 2631-2643.

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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.",

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doi = "10.3762/bjoc.15.256",

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Nanangenines : drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis. / Lacey, Heather J.; Gilchrist, Cameron L. M.; Crombie, Andrew; Kalaitzis, John A.; Vuong, Daniel; Rutledge, Peter J.; Turner, Peter; Pitt, John I.; Lacey, Ernest; Chooi, Yit-Heng; Piggott, Andrew M.

In: Beilstein Journal of Organic Chemistry, Vol. 15, 05.11.2019, p. 2631-2643.

Research output: Contribution to journal › Article

TY - JOUR

T1 - Nanangenines

T2 - drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis

AU - Lacey, Heather J.

AU - Gilchrist, Cameron L. M.

AU - Crombie, Andrew

AU - Kalaitzis, John A.

AU - Vuong, Daniel

AU - Rutledge, Peter J.

AU - Turner, Peter

AU - Pitt, John I.

AU - Lacey, Ernest

AU - Chooi, Yit-Heng

AU - Piggott, Andrew M.

N1 - 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.

PY - 2019/11/5

Y1 - 2019/11/5

N2 - 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.

AB - 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.

KW - Aspergillus

KW - Biosynthesis

KW - Drimane

KW - Secondary metabolites

KW - Sesquiterpenoid

KW - Terpenes

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10.3762/bjoc.15.256

Publisher version (open access)Final published version, 1 MBLicence: CC BY

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