Unique processes yielding pure azaphilones in Talaromyces atroroseus

Tolborg, Gerit; Ødum, Anders Sebastian Rosenkrans; Isbrandt, Thomas; Larsen, Thomas Ostenfeld; Workman, Mhairi

doi:10.1007/s00253-019-10112-w

Cited by 29 publications

(12 citation statements)

References 35 publications

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“…These approaches collectively defined the MonAzPs BGC of M. ruber M7 to extend from mrpigA to mrpigP , encompassing 16 genes. This assignment, supported by multiple lines of experimental evidence, offers a more secure basis for the retrobiosynthetic analysis of MonAzPs production, and provides a better focus for engineering approaches toward designer Monascus- type azaphilone pigments that may be useful to produce nutraceuticals, food and feed products, and specialty chemicals ( Tolborg et al, 2020 ). Additional transcriptional studies utilizing different cultivation conditions may further refine BGC border assignments.…”

Section: Discussionmentioning

confidence: 95%

“…The BGC responsible for MonAzPs production in Talaromyces (Penicillium) marneffei ATCC 18224 was also provisionally delimited during our comparative genomics process ( Figure 1 ). T. marneffei was reported to produce MonAzPs-type soluble red pigments ( Ogihara et al, 2000 , 2001 ; Frisvad et al, 2013 ; Arai et al, 2015 ; Jin et al, 2018 ; Morales-Oyervides et al, 2020 ; Tolborg et al, 2020 ), and accordingly, orthologs of most of the M. ruber M7 MonAzPs biosynthetic genes were found to be encoded in the T. marneffei ATCC 18224 BGC, albeit in a non-syntenic arrangement ( Chen et al, 2017 , 2019 ; Pavesi et al, 2021 ). While the genes corresponding to mrpigF , mrpigO , and mrpigL were absent from the T. marneffei BGC, similar genes to mrpigF and mrpigO are encoded elsewhere in the genome of this fungus ( Supplementary Table 4 ), and a mrpigL equivalent is not necessary for azaphilone pigment biosynthesis.…”

Section: Discussionmentioning

confidence: 99%

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An Integrated Approach to Determine the Boundaries of the Azaphilone Pigment Biosynthetic Gene Cluster of Monascus ruber M7 Grown on Potato Dextrose Agar

et al. 2021

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Monascus-type azaphilone pigments (MonAzPs) are produced in multi-thousand ton quantities each year and used as food colorants and nutraceuticals in East Asia. Several groups, including ours, described MonAzPs biosynthesis as a highly complex pathway with many branch points, affording more than 110 MonAzP congeners in a small group of fungi in the Eurotiales order. MonAzPs biosynthetic gene clusters (BGCs) are also very complex and mosaic-like, with some genes involved in more than one pathway, while other genes playing no apparent role in MonAzPs production. Due to this complexity, MonAzPs BGCs have been delimited differently in various fungi. Since most of these predictions rely primarily on bioinformatic analyses, it is possible that genes immediately outside the currently predicted BGC borders are also involved, especially those whose function cannot be predicted from sequence similarities alone. Conversely, some peripheral genes presumed to be part of the BGC may in fact lay outside the boundaries. This study uses a combination of computational and transcriptional analyses to predict the extent of the MonAzPs BGC in Monascus ruber M7. Gene knockouts and analysis of MonAzPs production of the mutants are then used to validate the prediction, revealing that the BGC consists of 16 genes, extending from mrpigA to mrpigP. We further predict that two strains of Talaromyces marneffei, ATCC 18224 and PM1, encode an orthologous but non-syntenic MonAzPs BGC with 14 genes. This work highlights the need to use comprehensive, integrated approaches for the more precise determination of secondary metabolite BGC boundaries.

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Section: Discussionmentioning

confidence: 95%

Section: Discussionmentioning

confidence: 99%

An Integrated Approach to Determine the Boundaries of the Azaphilone Pigment Biosynthetic Gene Cluster of Monascus ruber M7 Grown on Potato Dextrose Agar

et al. 2021

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“…As we have recently discovered for the compound class atrorosins (Isbrandt et al 2020 ), the incorporation of nitrogen into the isochromene system can be done using various primary amine containing compounds (Tolborg et al 2020 ). We speculate that the nitrogen, and additional carbons and oxygen in 3 originate from a decarboxylated serine moiety, i.e.…”

Section: Discussionmentioning

confidence: 99%

New azaphilones from Aspergillus neoglaber

et al. 2020

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Three new azaphilones, sassafrin E (1), sassafrin F (2), and sassafrinamine A (3), were isolated from the filamentous fungus Aspergillus neoglaber. The structures of the compounds were determined by nuclear magnetic resonance spectroscopy, and were found to be novel analogues of two already known compound classes; sassafrins and berkchaetoazaphilones. Sassafrin E and F were both oxygen containing, while sassafrinamine A additionally contained a nitrogen atom, originating from an aminoethanol moiety, as well as extensive conjugation resulting in an intense purple colour of the pure compound. The structure of sassafrin E was further confirmed using deuterium exchange experiments coupled with high-resolution tandem mass spectrometry.

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“…Increase in biomass development is not a must to enhance pigments production, as optimized conditions for development of fungal biomass not necessarily guarantee maximum production of metabolite [82]. In general, in the search for better yields, both, biomass and metabolite yield should increase [97]. Enhancement of metabolites yield can be achieved applying stressing conditions during fungal development, aiming at activating unconventional metabolic routes related to the production of substances linked to defense (biotic stress) or adaptation (abiotic stress).…”

Section: Yield Improvementmentioning

confidence: 99%

Recent Findings in Azaphilone Pigments

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Gomes

Cardoso

et al. 2021

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Filamentous fungi are known to biosynthesize an extraordinary range of azaphilones pigments with structural diversity and advantages over vegetal-derived colored natural products such agile and simple cultivation in the lab, acceptance of low-cost substrates, speed yield improvement, and ease of downstream processing. Modern genetic engineering allows industrial production, providing pigments with higher thermostability, water-solubility, and promising bioactivities combined with ecological functions. This review, covering the literature from 2020 onwards, focuses on the state-of-the-art of azaphilone dyes, the global market scenario, new compounds isolated in the period with respective biological activities, and biosynthetic pathways. Furthermore, we discussed the innovations of azaphilone cultivation and extraction techniques, as well as in yield improvement and scale-up. Potential applications in the food, cosmetic, pharmaceutical, and textile industries were also explored.

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Unique processes yielding pure azaphilones in Talaromyces atroroseus

Cited by 29 publications

References 35 publications

An Integrated Approach to Determine the Boundaries of the Azaphilone Pigment Biosynthetic Gene Cluster of Monascus ruber M7 Grown on Potato Dextrose Agar

An Integrated Approach to Determine the Boundaries of the Azaphilone Pigment Biosynthetic Gene Cluster of Monascus ruber M7 Grown on Potato Dextrose Agar

New azaphilones from Aspergillus neoglaber

Recent Findings in Azaphilone Pigments

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