Discovery and Heterologous Biosynthesis of the Burnettramic Acids: Rare PKS-NRPS-Derived Bolaamphiphilic Pyrrolizidinediones from an Australian Fungus, <i>Aspergillus burnettii</i>

Li, Hang; Gilchrist, Cameron L.M.; Lacey, Heather J.; Crombie, Andrew; Vuong, Daniel; Pitt, John I.; Lacey, Ernest; Chooi, Yit‐Heng; Piggott, Andrew M.

doi:10.1021/acs.orglett.8b04042

Cited by 57 publications

(72 citation statements)

References 36 publications

(60 reference statements)

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“…Alliacei species and not in any other species of sect. Flavi ( Goetz et al., 1985 , Liesch et al., 1985 , Liesch et al., 1988 , Mandelare et al., 2018 , Frisvad et al., 2019 , Li et al., 2019a , Morishita et al., 2019 ).…”

Section: Resultsmentioning

confidence: 99%

Classification of Aspergillus, Penicillium, Talaromyces and related genera (Eurotiales): An overview of families, genera, subgenera, sections, series and species

Houbraken¹,

Kocsubé²,

Visagie³

et al. 2020

Studies in Mycology

373

458

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The Eurotiales is a relatively large order of Ascomycetes with members frequently having positive and negative impact on human activities. Species within this order gain attention from various research fields such as food, indoor and medical mycology and biotechnology. In this article we give an overview of families and genera present in the Eurotiales and introduce an updated subgeneric, sectional and series classification for Aspergillus and Penicillium . Finally, a comprehensive list of accepted species in the Eurotiales is given. The classification of the Eurotiales at family and genus level is traditionally based on phenotypic characters, and this classification has since been challenged using sequence-based approaches. Here, we re-evaluated the relationships between families and genera of the Eurotiales using a nine-gene sequence dataset. Based on this analysis, the new family Penicillaginaceae is introduced and four known families are accepted: Aspergillaceae , Elaphomycetaceae , Thermoascaceae and Trichocomaceae . The Eurotiales includes 28 genera: 15 genera are accommodated in the Aspergillaceae ( Aspergillago , Aspergillus , Evansstolkia , Hamigera , Leiothecium , Monascus , Penicilliopsis , Penicillium , Phialomyces , Pseudohamigera , Pseudopenicillium , Sclerocleista , Warcupiella , Xerochrysium and Xeromyces ), eight in the Trichocomaceae ( Acidotalaromyces , Ascospirella , Dendrosphaera , Rasamsonia , Sagenomella , Talaromyces , Thermomyces , Trichocoma ), two in the Thermoascaceae ( Paecilomyces , Thermoascus ) and one in the Penicillaginaceae ( Penicillago ). The classification of the Elaphomycetaceae was not part of this study, but according to literature two genera are present in this family ( Elaphomyces and Pseudotulostoma ). The use of an infrageneric classification system has a long tradition in Aspergillus and Penicillium . Most recent taxonomic studies focused on the sectional l...

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Section: Resultsmentioning

confidence: 99%

Classification of Aspergillus, Penicillium, Talaromyces and related genera (Eurotiales): An overview of families, genera, subgenera, sections, series and species

Houbraken¹,

Kocsubé²,

Visagie³

et al. 2020

Studies in Mycology

373

458

View full text Add to dashboard Cite

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“…The tetramic acid skeleton is also found in other hybrid NPs such as equisetin, of which hybrids form other clades in the phylogeny (Clade Ib). The ME search focusing on these hybrids resulted in identification of seven hypothetical NP clades: burnettramic acid (characterized hybrid: BuaA 38 , 39 , number of hybrids: 24), Sch210972 (TasS 40 , 20), equisetin (EqxS 41 , 50), fusaridione (FsdS 41 , 5), Ib-α (25), Ib-β (12), and Ib-γ (16) (Schemes 4 and S3 , Tables S3 and S6 ). Hybrid NPs classified in this clade have unique polyketide side chains or moieties on the common tetramic acid moiety.…”

Section: Resultsmentioning

confidence: 99%

“…Considering that structurally related epicoccamides have only one hydroxyl group at the terminal position of the polyketide chain (Scheme S3), P450 might be responsible for the hydroxylation. Extended ME analysis showed that seven BGCs including that for burnettramic acid A possess a putative glycosyltransferase, which most likely catalyzes a glycosyltransfer reaction (Scheme S3) 38 . In contrast, equisetin (Ib-C) has a decalin skeleton, which undergoes no additional functionalizations during biosynthesis.…”

Section: Hybrid Gene Cluster Analysis Identification Of the Pyridonementioning

confidence: 99%

Predicting the chemical space of fungal polyketides by phylogeny-based bioinformatics analysis of polyketide synthase-nonribosomal peptide synthetase and its modification enzymes

Minami

Ugai

Ozaki

et al. 2020

Sci Rep

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Fungal polyketide synthase (PKS)–nonribosomal peptide synthetase (NRPS) hybrids are key enzymes for synthesizing structurally diverse hybrid natural products (NPs) with characteristic biological activities. Predicting their chemical space is of particular importance in the field of natural product chemistry. However, the unexplored programming rule of the PKS module has prevented prediction of its chemical structure based on amino acid sequences. Here, we conducted a phylogenetic analysis of 884 PKS–NRPS hybrids and a modification enzyme analysis of the corresponding biosynthetic gene cluster, revealing a hidden relationship between its genealogy and core structures. This unexpected result allowed us to predict 18 biosynthetic gene cluster (BGC) groups producing known carbon skeletons (number of BGCs; 489) and 11 uncharacterized BGC groups (171). The limited number of carbon skeletons suggests that fungi tend to select PK skeletons for survival during their evolution. The possible involvement of a horizontal gene transfer event leading to the diverse distribution of PKS–NRPS genes among fungal species is also proposed. This study provides insight into the chemical space of fungal PKs and the distribution of their biosynthetic gene clusters.

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“…In addition to ilicicolin H, a shunt metabolite ilicicolin J (78) was isolated with an MIC of 6.3 µ g/mL against C. albicans [66]. Heterologous expression was also employed to confirm the biosynthetic gene cluster involved in the production of the burnettramic acids A and B (79 and 80) in Aspergillus burnettii FRR 5400 [67]. Burnettramic acid A had an MIC value < 1 μg/mL against C. albicans while burnettramic acid B was slightly less active with values of 1-2 μg/mL.…”

Section: Natural Product Antifungal Leads From Fungimentioning

confidence: 99%

A Decade of Antifungal Leads from Natural Products: 2010–2019

et al. 2019

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In this review, we discuss novel natural products discovered within the last decade that are reported to have antifungal activity against pathogenic species. Nearly a hundred natural products were identified that originate from bacteria, algae, fungi, sponges, and plants. Fungi were the most prolific source of antifungal compounds discovered during the period of review. The structural diversity of these antifungal leads encompasses all the major classes of natural products including polyketides, shikimate metabolites, terpenoids, alkaloids, and peptides.

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Discovery and Heterologous Biosynthesis of the Burnettramic Acids: Rare PKS-NRPS-Derived Bolaamphiphilic Pyrrolizidinediones from an Australian Fungus, Aspergillus burnettii

Cited by 57 publications

References 36 publications

Classification of Aspergillus, Penicillium, Talaromyces and related genera (Eurotiales): An overview of families, genera, subgenera, sections, series and species

Classification of Aspergillus, Penicillium, Talaromyces and related genera (Eurotiales): An overview of families, genera, subgenera, sections, series and species

Predicting the chemical space of fungal polyketides by phylogeny-based bioinformatics analysis of polyketide synthase-nonribosomal peptide synthetase and its modification enzymes

A Decade of Antifungal Leads from Natural Products: 2010–2019

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