Pseudallicins A–D: Four Complex Ovalicin Derivatives from <i>Pseudallescheria boydii</i> SNB-CN85

Sorres, Jonathan; Nirma, Charlotte; Éparvier, Véronique; Stien, Didier

doi:10.1021/acs.orglett.7b01671

Cited by 8 publications

(9 citation statements)

References 14 publications

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“…Previous studies in our group led to the isolation of six fungal strains of the genus Pseudallescheria from three different termite colonies (out of eight nests harvested) [20][21][22]. Our preliminary results suggest that the fungi genus Pseudallescheria may be frequently associated with termites, exchanged between individuals, and spread in the nest.…”

Section: Introductionmentioning

confidence: 55%

“…It was hypothesized that this fungus has the ability to protect termites, its macroscopic host. Pseudallescheria boydii is a fungus frequently isolated from insects [20][21][22][23]. It seems that P. boydii has a broad host range, mainly described as saprophytic, frequently present in soil or polluted water but also on the surface of seaweed or endophytic [24,25] and in humans by causing invasive infections mainly in immunocompromised hosts but also in immunocompetent hosts [26].…”

Section: Introductionmentioning

confidence: 99%

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Antiparasitic Ovalicin Derivatives from Pseudallescheria boydii, a Mutualistic Fungus of French Guiana Termites

et al. 2022

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Social insects are in mutualism with microorganisms, contributing to their resistance against infectious diseases. The fungus Pseudallescheria boydii SNB-CN85 isolated from termites produces ovalicin derivatives resulting from the esterification of the less hindered site of the ovalicin epoxide by long-chain fatty acids. Their structures were elucidated using spectroscopic analysis and semisynthesis from ovalicin. For ovalicin, these compounds displayed antiprotozoal activities against Plasmodium falciparum and Trypanosoma brucei, with IC50 values of 19.8 and 1.1 µM, respectively, for the most active compound, i.e., ovalicin linoleate. In parallel, metabolomic profiling of a collection of P. boydii strains associated with termites made it possible to highlight this class of compounds together with tyroscherin derivatives in all strains. Finally, the complete genome of P. boydii strains was obtained by sequencing, and the cluster of potential ovalicin and ovalicin biosynthesis genes was annotated. Through these metabolomic and genomic analyses, a new ovalicin derivative named boyden C, in which the 6-membered ring of ovalicin was opened by oxidative cleavage, was isolated and structurally characterized.

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Section: Introductionmentioning

confidence: 55%

Section: Introductionmentioning

confidence: 99%

Antiparasitic Ovalicin Derivatives from Pseudallescheria boydii, a Mutualistic Fungus of French Guiana Termites

et al. 2022

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“…Three biosynthetic pathways are possible from this azaphilone scaffold (12). The rst pathway leads to the production of sclerotiorin (4).…”

Section: Resultsmentioning

confidence: 99%

“…In the literature, the research group of V. Eparvier described examples of antimicrobial compounds produced by termite's symbiotic microorganisms [6,10,11,12,13,14,15,16]. Among the studied termiteassociated microorganisms, chlorinated metabolites of ilicicolin and azaphilone families were isolated from Neonectria discophora and Penicillium sclerotiorum fungal strains [14,15,16].…”

Section: Introductionmentioning

confidence: 99%

Combining OSMAC, Metabolomic and Genomic Methods on Termite Symbiotic Fungi for the Production and Annotation of Halogenated Azaphilones and Ilicicolins

Hebra

Pollet

Touboul

et al. 2022

Preprint

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We mined a collection of termite mutualistic strains from French Guiana to explore metabolites of symbiotic microorganisms. Molecular networks reconstructed from a metabolomic analysis using LC-ESI-MS/MS methodology led us to identify two families of chlorinated polyketides, i.e. azaphilones from Penicillium sclerotiorum and ilicolins from Neonectria discophora. To define the biosynthetic pathways related to these two types of scaffolds, we used a whole genome sequencing approach followed by hybrid assembly from short and long reads. We found two biosynthetic gene clusters including two FAD-dependent halogenases. To exploit the enzymatic promiscuity of the two identified FAD halogenases, we sought to biosynthesize novel halogenated metabolites. An OSMAC strategy was used and resulted in the production of brominated analogs of ilicicolins and azaphilones as well as iodinated analogs of azaphilones.

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“…The exploration of secondary metabolites involved in microbial-host interactions has emerged as a successful strategy to identify novel chemical entities and to shed light on the ecology and evolution of defensive association (Beemelmanns et al, 2016;Cantley and Clardy, 2015). These associations are well described in social insects which include ants, bees, termites and wasps, although termites are somewhat less studied than others (Carr et al, 2012;Matsui et al, 2012;Nirma et al, 2015aNirma et al, , 2015bNirma et al, , 2013Nowak et al, 2010;Sorres et al, 2017;Yan et al, 2011). Indeed, termites microorganisms interactions have been explored mainly to study trophobioses (Carr et al, 2012;Nowak et al, 2010;Yan et al, 2011).…”

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confidence: 99%

Tyroscherin and tyroscherin analogs from Pseudallescheria boydii SNB-CN85 isolated from termite Termes cf. hispaniolae

Sorres

Nirma

Barthélemy

et al. 2017

Phytochemistry Letters

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Two new tyroscherin derivatives: N-methyl-tyroscherone (2) and tyroscherin N,O-acetonide (3), as well as two known secondary metabolites tyroscherin (1) and pseurotin A (4), were isolated from a solid culture of the termite-borne fungus Pseudallescheria boydii SNB-CN85. The structures were elucidated by spectroscopic analysis and chemical modification. Compound 3 was synthesized from tyroscherin (1) in the free amine form by heating in deuterated acetone, followed by deuterium-proton exchange in MeOH. All compounds were tested for their antimicrobial activities on C. albicans and S. aureus, and 2 and 3 exhibited minimal inhibitory concentrations between 128 and 8 g.mL-1 .

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Pseudallicins A–D: Four Complex Ovalicin Derivatives from Pseudallescheria boydii SNB-CN85

Cited by 8 publications

References 14 publications

Antiparasitic Ovalicin Derivatives from Pseudallescheria boydii, a Mutualistic Fungus of French Guiana Termites

Antiparasitic Ovalicin Derivatives from Pseudallescheria boydii, a Mutualistic Fungus of French Guiana Termites

Combining OSMAC, Metabolomic and Genomic Methods on Termite Symbiotic Fungi for the Production and Annotation of Halogenated Azaphilones and Ilicicolins

Tyroscherin and tyroscherin analogs from Pseudallescheria boydii SNB-CN85 isolated from termite Termes cf. hispaniolae

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