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

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 sup...

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Main Authors:	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
Format:	Article
Language:	English
Published:	Beilstein-Institut 2019-11-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	aspergillus biosynthesis drimane secondary metabolites sesquiterpenoid terpenes
Online Access:	https://doi.org/10.3762/bjoc.15.256

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spelling	doaj-a92b5119f02d432d8988eaae7004b64f2021-02-02T06:50:07ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972019-11-011512631264310.3762/bjoc.15.2561860-5397-15-256Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensisHeather J. Lacey0Cameron L. M. Gilchrist1Andrew Crombie2John A. Kalaitzis3Daniel Vuong4Peter J. Rutledge5Peter Turner6John I. Pitt7Ernest Lacey8Yit-Heng Chooi9Andrew M. Piggott10Microbial Screening Technologies, Smithfield, NSW 2164, AustraliaSchool of Molecular Sciences, The University of Western Australia, WA 6009, AustraliaMicrobial Screening Technologies, Smithfield, NSW 2164, AustraliaMicrobial Screening Technologies, Smithfield, NSW 2164, AustraliaMicrobial Screening Technologies, Smithfield, NSW 2164, AustraliaSchool of Chemistry, The University of Sydney, NSW 2006, AustraliaSchool of Chemistry, The University of Sydney, NSW 2006, AustraliaMicrobial Screening Technologies, Smithfield, NSW 2164, AustraliaMicrobial Screening Technologies, Smithfield, NSW 2164, AustraliaSchool of Molecular Sciences, The University of Western Australia, WA 6009, AustraliaDepartment of Molecular Sciences, Macquarie University, NSW 2109, AustraliaChemical 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.https://doi.org/10.3762/bjoc.15.256aspergillusbiosynthesisdrimanesecondary metabolitessesquiterpenoidterpenes
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	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
spellingShingle	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 Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis Beilstein Journal of Organic Chemistry aspergillus biosynthesis drimane secondary metabolites sesquiterpenoid terpenes
author_facet	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
author_sort	Heather J. Lacey
title	Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis
title_short	Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis
title_full	Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis
title_fullStr	Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis
title_full_unstemmed	Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis
title_sort	nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel australian fungus, aspergillus nanangensis
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2019-11-01
description	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.
topic	aspergillus biosynthesis drimane secondary metabolites sesquiterpenoid terpenes
url	https://doi.org/10.3762/bjoc.15.256
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Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis

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