New natural products isolated from Metarhizium robertsii ARSEF 23 by chemical screening and identification of the gene cluster through engineered biosynthesis in Aspergillus nidulans A1145

Kato, Hiroki; Tsunematsu, Yuta; Yamamoto, Tsuyoshi; Namiki, Takuya; Kishimoto, Shinji; Noguchi, Hiroshi; Watanabe, Kenji

doi:10.1038/ja.2016.54

Cited by 32 publications

(32 citation statements)

References 30 publications

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“…This finding would suggest that these metabolites may contribute to fungal entomopathogenicity. Likewise, by using a high resolution MS technique, the immunosuppressive compounds α-pyrone diterpenoids subglutinols were identified in M. robertsii (Kato et al, 2016). In contrast to the compounds mentioned above, these diterpenoids were originally identified from the plant pathogen Fusarium subglutinans (Lee et al, 1995).…”

Section: Discussionmentioning

confidence: 99%

Metabolic Conservation and Diversification of Metarhizium Species Correlate with Fungal Host-Specificity

Luo

et al. 2016

Front. Microbiol.

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The ascomycete genus Metarhizium contains several species of insect pathogenic fungi ranging from specialists with narrow host ranges to generalists that can infect diverse invertebrates. Genetic and metabolic conservations and diversifications of Metarhizium species are not well understood. In this study, using the genome information of seven Metarhizium species, we performed a comparative analysis of gene clusters involved in secondary metabolisms (SMs) in these species. The results revealed that the generalist species contain more SM gene clusters than the specialists, and that both conserved and divergent evolutions may have occurred in SM genes during fungal speciation. In particular, the loss/gain events, as well as gene mutagenesis, are evident for the gene cluster responsible for the biosynthesis of non-ribosomal cyclopeptide destruxins. The presence of conserved SM gene clusters in Metarhizium and other divergently evolved insect pathogenic fungi implies their link to fungal entomopathogenicity. Mass spectrometry based metabolomic analyses were also conducted to investigate the chemical diversities of seven Metarhizium species. Consistent with the evolutionary relationships of SM genes among the seven species, significant differences are observed in fungal metabolic profiles, whether the same or different metabolites are produced in different species. Clustering analysis based on the metabolome data revealed that Metarhizium species could be grouped based on their association to fungal host specificity. Our metabolomics-based methods also facilitate the identification of bioactive metabolites that have not been reported previously in Metarhizium. The results of this study will benefit future investigations of the chemical biology of insect-fungal interactions.

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Section: Discussionmentioning

confidence: 99%

Metabolic Conservation and Diversification of Metarhizium Species Correlate with Fungal Host-Specificity

Luo

et al. 2016

Front. Microbiol.

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“…We reconstituted the dpas and dpma pathways by introducing an FMO gene dpasF or a BBE gene dpmaF into AO-dpasABCDE to give AO-dpasABCDEF and AO-dpasABCDE-dpmaF. AO-dpasABCDE-dpmaF provided subglutinols A (5, 89 mg L −1 ) and B (6, 6 mg L −1 ) as previously suggested in the sub cluster 46 ( Supplementary Fig. 12).…”

Section: Resultsmentioning

confidence: 83%

“…3d. Considering previously reported DDPs and their producing fungi, the dpch and dpma pathways may produce higginsianin A 40 and subglutinol A 38,46 , respectively. However, the orphan dpfg, dpmp and dpas pathways may provide new DDP analogues.…”

Section: Resultsmentioning

confidence: 89%

“…3a). In addition, the functions of a non-reducing polyketide synthase (NR-PKS) SubA, geranylgeranyl diphosphate synthase (GGPPS) SubD and prenyltransferase (PT) SubC have been identified by a heterologous expression study 46 . We perform genome mining based on this information and find putative DDP gene clusters distributed in five fungal genera Arthrinium, b Genome mining and reconstruction of the related pathways to produce natural analogues.…”

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confidence: 99%

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Synthetic biology based construction of biological activity-related library of fungal decalin-containing diterpenoid pyrones

et al. 2020

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A synthetic biology method based on heterologous biosynthesis coupled with genome mining is a promising approach for increasing the opportunities to rationally access natural product with novel structures and biological activities through total biosynthesis and combinatorial biosynthesis. Here, we demonstrate the advantage of the synthetic biology method to explore biological activity-related chemical space through the comprehensive heterologous biosynthesis of fungal decalin-containing diterpenoid pyrones (DDPs). Genome mining reveals putative DDP biosynthetic gene clusters distributed in five fungal genera. In addition, we design extended DDP pathways by combinatorial biosynthesis. In total, ten DDP pathways, including five native pathways, four extended pathways and one shunt pathway, are heterologously reconstituted in a genetically tractable heterologous host, Aspergillus oryzae, resulting in the production of 22 DDPs, including 15 new analogues. We also demonstrate the advantage of expanding the diversity of DDPs to probe various bioactive molecules through a wide range of biological evaluations.

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“…A literature review disclosed that since 2015, 20 new DTPs were isolated from various fungal strains. 4,[6][7][8][9][10][11] Despite the size of this family and their structural variety (Figure 1), they all share a similar biogenetic origin. However, there is a discrepancy in the way these compounds are classified and numbered since they are not viewed as one family.…”

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confidence: 99%

A Biosynthetic Numbering System for Diterpene Pyrones

Al-Khdhairawi

Cordell

Weber

et al. 2019

Natural Product Communications

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Diterpene pyrones, spiroditerpenoids, and brevianes are names given to a series of fungal meroterpenoids that share common structural features and a common biosynthetic pathway elaborated by multiple oxidations, rearrangements, and cyclizations to produce the observed structural diversity. A unifying approach to the numbering of these fungal metabolites, based on a common biosynthetic progenitor, a geranylgeranyl-pyrone hybrid, is presented. This proposal will foster simplicity through a standardized numbering system that can be applied to the known members of this family, as well as to future metabolites.

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New natural products isolated from Metarhizium robertsii ARSEF 23 by chemical screening and identification of the gene cluster through engineered biosynthesis in Aspergillus nidulans A1145

Cited by 32 publications

References 30 publications

Metabolic Conservation and Diversification of Metarhizium Species Correlate with Fungal Host-Specificity

Metabolic Conservation and Diversification of Metarhizium Species Correlate with Fungal Host-Specificity

Synthetic biology based construction of biological activity-related library of fungal decalin-containing diterpenoid pyrones

A Biosynthetic Numbering System for Diterpene Pyrones

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