The biosynthesis of asperugin in Aspergillus rugulosus

Ballantine, James A.; Ferrito, Victor; Hassall, C. H.

doi:10.1016/s0031-9422(00)84333-2

Cited by 6 publications

(4 citation statements)

References 8 publications

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“…Compounds 3 to 14 were identified as meroterpenoids, sharing the same skeleton of trihydroxyphthalaldehyde but with varying modifications on the side chain or the benzoic aldehyde. Compound 5 was elucidated as aspernidine F ( 28 ), and compound 8 was elucidated as asperugin B ( 29 ), referring to the published data. Compounds 13 and 14 were instable during isolation and converted to compound 8 (fig.…”

Section: Resultsmentioning

confidence: 99%

Fungal-fungal cocultivation leads to widespread secondary metabolite alteration requiring the partial loss-of-function VeA1 protein

et al. 2022

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Microbial communication has attracted notable attention as an indicator of microbial interactions that lead to marked alterations of secondary metabolites (SMs) in varied environments. However, the mechanisms responsible for SM regulation are not fully understood, especially in fungal-fungal interactions. Here, cocultivation of an endophytic fungus Epicoccum dendrobii with the model fungus Aspergillus nidulans and several other filamentous fungi triggered widespread alteration of SMs. Multiple silent biosynthetic gene clusters in A. nidulans were activated by transcriptome and metabolome analysis. Unprecedentedly, gene deletion and replacement proved that a partial loss-of-function VeA1 protein, but not VeA, was associated with the widespread SM changes in both A. nidulans and A. fumigatus during cocultivation. VeA1 regulation required the transcription factor SclB and the velvet complex members LaeA and VelB for producing aspernidines as representative formation of SMs in A. nidulans . This study provides new insights into the mechanism that trigger metabolic changes during fungal-fungal interactions.

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Section: Resultsmentioning

confidence: 99%

Fungal-fungal cocultivation leads to widespread secondary metabolite alteration requiring the partial loss-of-function VeA1 protein

et al. 2022

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“…8). Although the biosynthetic origin of diorcinol is uncertain, similar diphenyl ethers appear to be derived from orseilinic acid (2, 27), which is the starting compound for the biosynthesis of several characterized secondary metabolites in a variety of fungi ( 25): it is the precursor of penicillic acid in Penicillium cyclopium (5), of fumagatin in Aspergillusfumagatus (27), of flavipin in Aspergillusflavipes (19), and of asperugin in Aspergillus rugulosus (2). Although none of these compounds have been reported to be produced by A. nidulans, A. rugulosus is a closely related species (21).…”

Section: Discussionmentioning

confidence: 99%

“…In fact, chemical investigations by Hassall and co-workers dating from some 20 years ago showed that asperugin (a farnesyl derivative of orsellinic acid) and some other presumed intermediates in its synthesis were present in certain variant strains described as sparsely conidial and acleistothecial ( 9), but they were undetectable in strains with normal morphology (4). One of the accumulated compounds was identified as diorcinol (3), which was proposed to be a shunt product of the main pathway leading from orsellinic acid to asperugin (2). The primary emphasis of this work, however, was on the chemistry of fungal products; no further studies on the genetic nature of the variant strains were reported.…”

Section: Discussionmentioning

confidence: 99%

Mutants of Aspergillus nidulans blocked at an early stage of sporulation secrete an unusual metabolite

Butnick¹,

Yager²,

Hermann³

et al. 1984

J Bacteriol

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Mutants of AspergiUlus nidulans defective in conidiation (asexual sporulation) can be classified according to whether they are blocked before or after induction of conidiation. Mutants blocked before induction (preinduction mutants) appear to be unable to respond to the inducing stimulus and thus are defective in one of the earliest events in the sporulation process. Three preinduction mutants have been isolated and characterized. Each was found to exhibit the same pleiotropic phenotype: they also were defective in sexual sporulation and secreted a set of phenolic metabolites at a level much higher than did wild type or mutants blocked at later stages of conidiation. One of the metabolites has been identified as the antibiotic diorcinal (3,3'-dihydroxy-5,5'dimethyldiphenyl ether) which is known to be involved in the synthesis of certain farnesyl phenols of unknown function. These results suggest that preinduction mutants are blocked in a phenolic metabolic pathway, one or more product of which participates in the initiation of sporulation.

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“…6,8-dihydroxy-3,5,7-trimethyl-isochroman (8) was previously reported exclusively as a SM of Stachybotrys cylindrospora , an endosymbiont of aspen trees [35] . It is interesting to note that although asperlin (9) has been isolated from several Aspergillus sp [36] , and that asperugin A (11) and B (12) were previously isolated from Aspergillus rugulosus [37] , [38] , they were not detected in the crude extract of the Aspergillus -derived heterologous host, FAC- An HH.…”

Section: Resultsmentioning

confidence: 99%

Activation of cryptic biosynthetic gene clusters by fungal artificial chromosomes to produce novel secondary metabolites

Wu,

Stierle,

Stierle

et al. 2023

AIMSMICRO

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<abstract> <p>In 2017, we reported the discovery of Berkeleylactone A (BPLA), a novel, potent antibiotic produced exclusively in co-culture by two extremophilic fungi, <italic>Penicillium fuscum</italic> and <italic>P. camembertii/clavigerum</italic>, which were isolated from the Berkeley Pit, an acid mine waste lake, in Butte, Montana. Neither fungus synthesized BPLA when grown in axenic culture. Recent studies suggest that secondary metabolites (SMs) are often synthesized by enzymes encoded by co-localized genes that form “biosynthetic gene clusters” (BGCs), which might remain <italic>silent</italic> (inactive) under various fermentation conditions. Fungi may also harbor cryptic BGCs that are not associated with previously characterized molecules.</p> <p>We turned to the tools of Fungal Artificial Chromosomes (FAC)-Next-Gen-Sequencing (NGS) to understand how co-culture activated cryptic biosynthesis of BPLA and several related berkeleylactones and to further investigate the true biosynthetic potential of these two fungi. FAC-NGS enables the capture of BGCs as individual FACs for heterologous expression in a modified strain of <italic>Aspergillus nidulans</italic> (heterologous host, FAC-<italic>An</italic>HH). With this methodology, we created ten BGC-FACs that yielded fourteen different SMs, including strobilurin, which was previously isolated exclusively from basidiomycetes. Eleven of these compounds were not detected in the extracts of the FAC-<italic>An</italic>HH. Of this discrete set, only the novel compound citreohybriddional had been isolated from either <italic>Penicillium</italic> sp. before and only at very low yield. We propose that through heterologous expression, FACs activated these silent BGCs, resulting in the synthesis of new natural products (NPs) with yields as high as 50%–60% of the crude organic extracts.</p> </abstract>

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The biosynthesis of asperugin in Aspergillus rugulosus

Cited by 6 publications

References 8 publications

Fungal-fungal cocultivation leads to widespread secondary metabolite alteration requiring the partial loss-of-function VeA1 protein

Fungal-fungal cocultivation leads to widespread secondary metabolite alteration requiring the partial loss-of-function VeA1 protein

Mutants of Aspergillus nidulans blocked at an early stage of sporulation secrete an unusual metabolite

Activation of cryptic biosynthetic gene clusters by fungal artificial chromosomes to produce novel secondary metabolites

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