A Non-Canonical NRPS Is Involved in the Synthesis of Fungisporin and Related Hydrophobic Cyclic Tetrapeptides in Penicillium chrysogenum

Ali, Hazrat; Ries, Marco; Lankhorst, Peter P.; Hoeven, R. A. M. van der; Schouten, Olaf; Noga, Marek; Hankemeier, Thomas; Peij, Noël N. M. E. van; Bovenberg, Roel A. L.; Vreeken, Rob J.; Driessen, Arnold J. M.

doi:10.1371/journal.pone.0098212

Cited by 45 publications

(58 citation statements)

References 34 publications

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“…Originally characterized in A. nidulans, currently there is no known property or function for this metabolite [39]. However, the non-ribosomal synthetase (NRPS) generating nidulanin is also involved in synthesis of fungisporin [44], which has been shown to have antibacterial properties [45].…”

Section: Results and Discussion (A) Twenty-six Clustersmentioning

confidence: 99%

Secondary metabolite arsenal of an opportunistic pathogenic fungus

Bignell

Cairns²,

Throckmorton

et al. 2016

Phil. Trans. R. Soc. B

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Section: Results and Discussion (A) Twenty-six Clustersmentioning

confidence: 99%

Secondary metabolite arsenal of an opportunistic pathogenic fungus

Bignell

Cairns²,

Throckmorton

et al. 2016

Phil. Trans. R. Soc. B

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“…The two N- methylated cyclic tetrapeptides, onychocins A and B, are likely to be produced by a tetramodular NRPS based on the collinearity rule commonly observed in both bacterial and fungal NRPSs [60]. However, given that onychocins A and B consist of two pairs of similar amino acids ( l -Phe and l -Val or l -Ile), it is possible that the tetrapeptides are biosynthesised by non-canonical NRPSs with functional domains that are capable of acting iteratively, such as those commonly observed in cyclooligomer depsipeptide biosynthesis [61] and more recently demonstrated in the biosynthesis of fungisporin from Penicillium chrysogenum [62]. Interestingly, of all the multimodular NRPSs encoded in the genome of A .…”

Section: Resultsmentioning

confidence: 99%

Aspergillus hancockii sp. nov., a biosynthetically talented fungus endemic to southeastern Australian soils

Pitt

Lange

Lacey³

et al. 2017

PLoS ONE

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Aspergillus hancockii sp. nov., classified in Aspergillus subgenus Circumdati section Flavi, was originally isolated from soil in peanut fields near Kumbia, in the South Burnett region of southeast Queensland, Australia, and has since been found occasionally from other substrates and locations in southeast Australia. It is phylogenetically and phenotypically related most closely to A. leporis States and M. Chr., but differs in conidial colour, other minor features and particularly in metabolite profile. When cultivated on rice as an optimal substrate, A. hancockii produced an extensive array of 69 secondary metabolites. Eleven of the 15 most abundant secondary metabolites, constituting 90% of the total area under the curve of the HPLC trace of the crude extract, were novel. The genome of A. hancockii, approximately 40 Mbp, was sequenced and mined for genes encoding carbohydrate degrading enzymes identified the presence of more than 370 genes in 114 gene clusters, demonstrating that A. hancockii has the capacity to degrade cellulose, hemicellulose, lignin, pectin, starch, chitin, cutin and fructan as nutrient sources. Like most Aspergillus species, A. hancockii exhibited a diverse secondary metabolite gene profile, encoding 26 polyketide synthase, 16 nonribosomal peptide synthase and 15 nonribosomal peptide synthase-like enzymes.

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“…However, seventeen core biosynthetic genes coding to NRPS enzymes (51%) presented hit to multi-modular NRPS enzymes involved in the biosynthesis of cyclic peptides, including: the cyclic tetrapeptides cyclosporin (SimA), fungisporin (HcpA) and apicidin (APS1) as well as the cyclohexadepsipeptide destruxins (DtxS1) (ESI Table 2 †). [39][40][41][42] Other 10 NRPS core genes (30%) presented homology to hybrid polyketide synthase/nonribosomal peptide synthetase LcsA (8 related core genes) and EasA (2 related core genes), respectively related to production of leucinostatin A and emericellamide A. 43,44 Finally, 5 NRPS genes (15%) presented similarity to the trimodular NRPS Afu6g12080, which is associated to biosynthesis of fumiquinazoline (FQ) peptidyl alkaloids (ESI Table 2 †).…”

Section: Resultsmentioning

confidence: 99%