Fungal naphtho-γ-pyrones—secondary metabolites of industrial interest

Choque, Élodie; Rayess, Youssef El; Filho, José Tadeu Raynal Rocha; Mathieu, Florence

doi:10.1007/s00253-014-6295-1

Cited by 37 publications

(35 citation statements)

References 111 publications

(176 reference statements)

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“…SMURF identifies this PKS as a non-clusterized PKS, validating the result previously obtained on A. tubingensis CBS 134.48 [20]. Those results are in agreement with results previously obtained in different A. niger strains showing that the PKS involved in biosynthesis of both NGPs and DHN-melanin is non-clusterized [2,51,52]. For this reason, we suggest that cluster 54 PKS is homologue to AlbA / PksP and most likely the entire SM cluster is not solely involved in NGPs biosynthesis.…”

Section: Focus On Sm Production With Potential For Industrial Applicasupporting

confidence: 91%

“…Depending of the species, produced NGP dimers can vary: aurasperones, asperspyrones, nigerasperones or fonsecinones [2]. LC-MS analysis of a methanol extract indicates that A. tubingensis G131 is able to produce the NGPs monomers fonsecin and rubrofusarin and NGPs dimers members of aurasperones (Fig.…”

Section: Focus On Sm Production With Potential For Industrial Applicamentioning

confidence: 99%

“…It is described that this PKS is involved in the formation of YWA1, which is a common precursor of both NGPs and DHN-melanin pigments [52]. After this step, little is known about NGPs biosynthesis [2].…”

Section: Focus On Sm Production With Potential For Industrial Applicamentioning

confidence: 99%

“…Due to their versatile metabolism, those fungi are one of the most prolific sources of enzymes, organic acids and secondary metabolites (SM) with biomedical and biotechnological interests [1][2][3][4]. Already described as non-mycotoxins producer in comparison to A. niger [5][6][7][8][9], A. tubingensis, which is part of the A. niger clade of the black Aspergilli, represents a good alternative for metabolites production in industrial fermentation and is already used for some applications [10][11][12].…”

Section: Introductionmentioning

confidence: 99%

“…Besides, strains of this clade are remarkable producers of secondary metabolites of industrial, agricultural and economic importance. For example, they have the potential to produce compounds such as asperazine, which has antibiotic properties, or Naphtho-Gamma-Pyrones (NGPs), showing antioxidant, anticancer or antibiotic properties [1,2]. However, they can also produce mycotoxins such as ochratoxin A (OTA) and fumonisin B 2 , which are major concerns in risk assessment in the food chain [5].…”

Section: Introductionmentioning

confidence: 99%

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Whole-genome sequencing of Aspergillus tubingensis G131 and overview of its secondary metabolism potential

Choque

Klopp²,

Valière³

et al. 2018

BMC Genomics

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Background: Black Aspergilli represent one of the most important fungal resources of primary and secondary metabolites for biotechnological industry. Having several black Aspergilli sequenced genomes should allow targeting the production of certain metabolites with bioactive properties. Results: In this study, we report the draft genome of a black Aspergilli, A. tubingensis G131, isolated from a French Mediterranean vineyard. This 35 Mb genome includes 10,994 predicted genes. A genomic-based discovery identifies 80 secondary metabolites biosynthetic gene clusters. Genomic sequences of these clusters were blasted on 3 chosen black Aspergilli genomes: A. tubingensis CBS 134.48, A. niger CBS 513.88 and A. kawachii IFO 4308. This comparison highlights different levels of clusters conservation between the four strains. It also allows identifying seven unique clusters in A. tubingensis G131. Moreover, the putative secondary metabolites clusters for asperazine and naphthogamma-pyrones production were proposed based on this genomic analysis. Key biosynthetic genes required for the production of 2 mycotoxins, ochratoxin A and fumonisin, are absent from this draft genome. Even if intergenic sequences of these mycotoxins biosynthetic pathways are present, this could not lead to the production of those mycotoxins by A. tubingensis G131.

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Section: Focus On Sm Production With Potential For Industrial Applicasupporting

confidence: 91%

Section: Focus On Sm Production With Potential For Industrial Applicamentioning

confidence: 99%

Section: Focus On Sm Production With Potential For Industrial Applicamentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Whole-genome sequencing of Aspergillus tubingensis G131 and overview of its secondary metabolism potential

Choque

Klopp²,

Valière³

et al. 2018

BMC Genomics

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Enzymology of Anthraquinone‐γ‐Pyrone Ring Formation in Complex Aromatic Polyketide Biosynthesis

et al. 2018

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Aromatic‐fused γ‐pyrones are structural features of many bioactive natural products and valid scaffolds for medicinal chemistry. However, the enzymology of their formation has not been completely established. Now it is demonstrated that TxnO9, a CalC‐like protein belonging to a START family, functions as an unexpected anthraquinone‐γ‐pyrone synthase involved in the biosynthesis of antitumor antibiotic trioxacarcin A (TXN‐A). Structural analysis by NMR identified a likely substrate/product‐binding mode and putative key active sites of TxnO9, which allowed an enzymatic mechanism to be proposed. Moreover, a subset of uncharacterized homologous proteins bearing an unexamined Lys‐Thr dyad exhibit the same function. Therefore, the functional assignment and mechanistic investigation of this γ‐pyrone synthase elucidated an undescribed step in TXN‐A biosynthesis, and the discovery of this new branch of polyketide heterocyclases expands the functions of the START superfamily.

show abstract

Enzymology of Anthraquinone‐γ‐Pyrone Ring Formation in Complex Aromatic Polyketide Biosynthesis

et al. 2018

View full text Add to dashboard Cite

Aromatic-fused γ-pyrones are structural features of many bioactive natural products and valid scaffolds for medicinal chemistry. However, the enzymology of their formation has not been completely established. Now it is demonstrated that TxnO9, a CalC-like protein belonging to a START family, functions as an unexpected anthraquinone-γ-pyrone synthase involved in the biosynthesis of antitumor antibiotic trioxacarcin A (TXN-A). Structural analysis by NMR identified a likely substrate/product-binding mode and putative key active sites of TxnO9, which allowed an enzymatic mechanism to be proposed. Moreover, a subset of uncharacterized homologous proteins bearing an unexamined Lys-Thr dyad exhibit the same function. Therefore, the functional assignment and mechanistic investigation of this γ-pyrone synthase elucidated an undescribed step in TXN-A biosynthesis, and the discovery of this new branch of polyketide heterocyclases expands the functions of the START superfamily.

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Fungal naphtho-γ-pyrones—secondary metabolites of industrial interest

Cited by 37 publications

References 111 publications

Whole-genome sequencing of Aspergillus tubingensis G131 and overview of its secondary metabolism potential

Whole-genome sequencing of Aspergillus tubingensis G131 and overview of its secondary metabolism potential

Enzymology of Anthraquinone‐γ‐Pyrone Ring Formation in Complex Aromatic Polyketide Biosynthesis

Enzymology of Anthraquinone‐γ‐Pyrone Ring Formation in Complex Aromatic Polyketide Biosynthesis

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