Isolation of a Novel Polyketide from Neodidymelliopsis sp.

Cadelis, Melissa M.; Gordon, Hugo; Grey, Alex; Geese, Soeren; Mulholland, Daniel R.; Weir, Bevan S.; Copp, Brent R.; Wiles, Siouxsie

doi:10.3390/molecules26113235

Cited by 8 publications

(8 citation statements)

References 20 publications

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“…Xylariolide D was isolated from different fungal strains, e.g., Xylaria sp. NCY2, Neodidymelliopsis sp., and Dictyosporium digitatum [ 29 , 30 , 31 ]. However, the gene cluster responsible for its biosynthesis has not been described previously.…”

Section: Discussionmentioning

confidence: 99%

Biosynthesis of Xylariolide D in Penicillium crustosum Implies a Chain Branching Reaction Catalyzed by a Highly Reducing Polyketide Synthase

Stierle

2022

JoF

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Fungi are important sources for the discovery of natural products. During the last decades, technological progress and the increasing number of sequenced genomes facilitated the exploration of new secondary metabolites. Among those, polyketides represent a structurally diverse group with manifold biological activities. In this study, we successfully used genome mining and genetic manipulation for functional proof of a polyketide biosynthetic gene cluster from the filamentous fungus Penicillium crustosum. Gene activation in the native host and heterologous expression in Aspergillus nidulans led to the identification of the xil cluster, being responsible for the formation of the 6-methyl-2-pyrone derivative xylariolide D. Feeding with 13C-labeled precursors supported the hypothesis of chain branching during the backbone formation catalyzed by a highly reducing fungal polyketide synthase. A cytochrome P450-catalyzed hydroxylation converts the PKS product to the final metabolite. This proved that just two enzymes are required for the biosynthesis of xylariolide D.

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Section: Discussionmentioning

confidence: 99%

Biosynthesis of Xylariolide D in Penicillium crustosum Implies a Chain Branching Reaction Catalyzed by a Highly Reducing Polyketide Synthase

Stierle

2022

JoF

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“…During this time, a 6 mm plug of agar was removed from each well using a biopsy punch twice. To screen for antimycobacterial activity, M. abscessus BSG301 [ 63 ] and M. marinum BSG101 [ 64 ] were resuspended in 0.8% Middlebrook 7H9 agar (Fort Richard, New Zealand) supplemented with 10% Middlebrook ADC enrichment media (Fort Richard, New Zealand) to a final concentration of approx. 10 7 colony forming units (CFU)/mL for M. abscessus and 10 8 CFU/mL for M. marinum .…”

Section: Methodsmentioning

confidence: 99%

“…Antimicrobial evaluation of the pure compounds against A. baumannii ATCC 19606, Candida albicans ATCC 90028, Cryptococcus neoformans ATCC 208821, E. coli ATCC 25922, K. pneumoniae ATCC 700603, P. aeruginosa ATCC 27853, and S. aureus ATCC 43300 (MRSA) was undertaken at the Community for Open Antimicrobial Drug Discovery at The University of Queensland (St. Lucia, Queensland, Australia) according to standard protocols [ 65 ] as previously described [ 63 , 66 , 67 ].…”

Section: Methodsmentioning

confidence: 99%

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Antimicrobial Natural Products from Plant Pathogenic Fungi

Cadelis

Pas

et al. 2023

Molecules

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Isolates of a variety of fungal plant pathogens (Alternaria radicina ICMP 5619, Cercospora beticola ICMP 15907, Dactylonectria macrodidyma ICMP 16789, D. torresensis ICMP 20542, Ilyonectria europaea ICMP 16794, and I. liriodendra ICMP 16795) were screened for antimicrobial activity against the human pathogenic bacteria Acinetobacter baumannii, Pseudomonas aeruginosa, Escherichia coli, Mycobacterium abscessus, and M. marinum and were found to have some activity. Investigation of the secondary metabolites of these fungal isolates led to the isolation of ten natural products (1–10) of which one was novel, (E)-4,7-dihydroxyoct-2-enoic acid (1). Structure elucidation of all natural products was achieved by a combination of NMR spectroscopy and mass spectrometry. We also investigated the antimicrobial activity of a number of the isolated natural products. While we did not find (E)-4,7-dihydroxyoct-2-enoic acid (1) to have any activity against the bacteria and fungi in our assays, we did find that cercosporin (7) exhibited potent activity against Methicillin resistant Staphylococcus aureus (MRSA), dehydro-curvularin (6) and radicicol (10) exhibited antimycobacterial activity against M. marinum, and brefeldin A (8) and radicicol (10) exhibited antifungal activity against Candida albicans. Investigation of the cytotoxicity and haemolytic activities of these natural products (6–8 and 10) found that only one of the four active compounds, radicicol (10), was non-cytotoxic and non-haemolytic.

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“…In this study, we used M. abscessus BSG301 ( Cadelis et al, 2021 ) and M. marinum BSG101 ( Dalton et al, 2017 ) which are stable bioluminescent derivatives transformed with the integrating plasmid pMV306G13ABCDE ( Andreu et al, 2010 ). We grew mycobacterial cultures with shaking (200 rpm) in Middlebrook 7H9 broth (Fort Richard, New Zealand) supplemented with 10% Middlebrook ADC enrichment media (Fort Richard, New Zealand), 0.4% glycerol (Sigma-Aldrich, New Zealand) and 0.05% tyloxapol (Sigma-Aldrich, New Zealand).…”

Section: Methodsmentioning

confidence: 99%

Screening of Fungi for Antimycobacterial Activity Using a Medium-Throughput Bioluminescence-Based Assay

et al. 2021

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There is a real and urgent need for new antibiotics able to kill Mycobacteria, acid-fast bacilli capable of causing multiple deadly diseases. These include members of the Mycobacterium tuberculosis complex, which causes the lung disease tuberculosis (TB) as well as non-tuberculous Mycobacteria (NTM) a growing cause of lung, skin, soft tissue, and other infections. Here we describe a medium-throughput bioluminescence-based pipeline to screen fungi for activity against Mycobacteria using the NTM species Mycobacterium abscessus and Mycobacterium marinum. We used this pipeline to screen 36 diverse fungal isolates from the International Collection of Microorganisms from Plants (ICMP) grown on a wide variety of nutrient-rich and nutrient-poor media and discovered that almost all the tested isolates produced considerable anti-mycobacterial activity. Our data also provides strong statistical evidence for the impact of growth media on antibacterial activity. Chemical extraction and fractionation of a subset of the ICMP isolates revealed that much of the activity we observed may be due to the production of the known anti-mycobacterial compound linoleic acid. However, we have identified several ICMP isolates that retained their anti-mycobacterial activity in non-linoleic acid containing fractions. These include isolates of Lophodermium culmigenum, Pseudaegerita viridis, and Trametes coccinea, as well as an unknown species of Boeremia and an isolate of an unknown genus and species in the family Phanerochaetaceae. Investigations are ongoing to identify the sources of their anti-mycobacterial activity and to determine whether any may be due to the production of novel bioactive compounds.

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Isolation of a Novel Polyketide from Neodidymelliopsis sp.

Cited by 8 publications

References 20 publications

Biosynthesis of Xylariolide D in Penicillium crustosum Implies a Chain Branching Reaction Catalyzed by a Highly Reducing Polyketide Synthase

Biosynthesis of Xylariolide D in Penicillium crustosum Implies a Chain Branching Reaction Catalyzed by a Highly Reducing Polyketide Synthase

Antimicrobial Natural Products from Plant Pathogenic Fungi

Screening of Fungi for Antimycobacterial Activity Using a Medium-Throughput Bioluminescence-Based Assay

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