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1. (Article ID: 9154)
Li H, Gilchrist CLM, Lacey HJ, Crombie A, Vuong D, Pitt JI, Lacey E, Chooi YH, Piggott AM
Discovery and heterologous biosynthesis of the burnettramic acids: Rare PKS-NRPS-derived bolaamphiphilic pyrrolizidinediones from an australian fungus, Aspergillus burnettii
Organic Letters 21(5) (2019)
1287-1291
The burnettramic acids are a new class of antibiotics from an Australian fungus Aspergillus burnettii. The rare bolaamphiphilic scaffold consists of β-D-mannose linked to a pyrrolizidinedione unit via a 26-carbon chain. The most abundant metabolite displayed potent in vitro antifungal activity. Comparative genomics identified the hybrid PKS-NRPS bua gene cluster, which was verified by heterologous pathway reconstitution in Aspergillus nidulans.
secondary metabolites, Aspergillus burnettii, pyrrolizidinediones
NCBI PubMed ID: 30735051Publication DOI: 10.1021/acs.orglett.8b04042Journal NLM ID: 100890393Publisher: American Chemical Society
Correspondence: Chooi YH
uwa.edu.au>; Piggott AM mq.edu.au>
Institutions: Department of Molecular Sciences, Macquarie University, Sydney, Australia, School of Molecular Sciences, The University of Western Australia, Perth, Australia, Microbial Screening Technologies Pty. Ltd., Smithfield, Australia, Commonwealth Scientific and Industrial Research Organisation, North Ryde, Australia
Methods: 13C NMR, 1H NMR, NMR-2D, DNA sequencing, biological assays, UV, extraction, RP-HPLC, cell growth, HR-ESI-MS, antibacterial assay, cytotoxicity assay, gene expression, antifungal activity test, BLAST, LC-DAD-MS, antiparasitic assay
The publication contains the following compound(s):
- Compound ID: 22315
|
b-D-Manp-(1-34)-Subst
Subst = burnettramic acid A aglycon = SMILES C[C@@H](C[C@@H](/{9}C(O)=C1C([C@]2(C{1}[C@@H](O)CN2C\1=O)[H])=O)C)CCCCCCC/C=C/C{23}[C@@H](CCC{27}[C@@H](CCCCCC{34}CO)O)O |
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Structure type: monomer
; 768.4898 [M-H]-
C41H71NO12
Trivial name: burnettramic acid A
Compound class: glycoside
Reference(s) to other database(s): GenDB:MK425157
- Compound ID: 22316
|
b-D-Manp-(1-34)-Subst
Subst = burnettramic acid B aglycon = SMILES CC(CC({9}C(O)=C1C([C@H]2C{1}[C@@H](O)CN2C1=O)=O)C)CCCCCCCCCC=CC{25}C(O)CCC{29}C(O)CCCC{34}CO |
Show graphically |
Structure type: monomer
; 768.4898 [M-H]-
C41H71NO12
Trivial name: burnettramic acid B
Compound class: glycoside
Reference(s) to other database(s): GenDB:MK425157
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