Isolation, Structural Analyses and Biological Activity Assays against Chronic Lymphocytic Leukemia of Two Novel Cytochalasins — Sclerotionigrin A and B

Petersen, Lene Maj; Bladt, Tanja Thorskov; Dürr, Claudia; Seiffert, Martina; Frisvad, Jens Christian; Gotfredsen, Charlotte Held; Larsen, Thomas Ostenfeld

doi:10.3390/molecules19079786

Cited by 11 publications

(2 citation statements)

References 33 publications

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“…A group of hybrids containing the cytochalasin producing hybrid A. clavatus 6366 (Additional file 9: Figure S1) shows a large phylogenetic distance to other hybrids, indicating that ACE1-like hybrids are rare in Aspergilli — sustaining the hypothesis by Khaldi et al [15]. Since A. sclerotioniger 605326 is the nearest neighbour of A. clavatus 6366 we predict this hybrid to produce sclerotionigrin [20], a cytochalasan.…”

Section: Resultssupporting

confidence: 73%

Genus level analysis of PKS-NRPS and NRPS-PKS hybrids reveals their origin in Aspergilli

2019

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BackgroundFilamentous fungi produce a vast amount of bioactive secondary metabolites (SMs) synthesized by e.g. hybrid polyketide synthase-nonribosomal peptide synthetase enzymes (PKS-NRPS; NRPS-PKS). While their domain structure suggests a common ancestor with other SM proteins, their evolutionary origin and dynamics in fungi are still unclear. Recent rational engineering approaches highlighted the possibility to reassemble hybrids into chimeras — suggesting molecular recombination as diversifying mechanism.ResultsPhylogenetic analysis of hybrids in 37 species – spanning 9 sections of Aspergillus and Penicillium chrysogenum – let us describe their dynamics throughout the genus Aspergillus. The tree topology indicates that three groups of PKS-NRPS as well as one group of NRPS-PKS hybrids developed independently from each other. Comparison to other SM genes lead to the conclusion that hybrids in Aspergilli have several PKS ancestors; in contrast, hybrids are monophyletic when compared to available NRPS genes — with the exception of a small group of NRPSs. Our analysis also revealed that certain NRPS-likes are derived from NRPSs, suggesting that the NRPS/NRPS-like relationship is dynamic and proteins can diverge from one function to another. An extended phylogenetic analysis including bacterial and fungal taxa revealed multiple ancestors of hybrids. Homologous hybrids are present in all sections which suggests frequent horizontal gene transfer between genera and a finite number of hybrids in fungi.ConclusionPhylogenetic distances between hybrids provide us with evidence for their evolution: Large inter-group distances indicate multiple independent events leading to the generation of hybrids, while short intra-group distances of hybrids from different taxonomic sections indicate frequent horizontal gene transfer. Our results are further supported by adding bacterial and fungal genera. Presence of related hybrid genes in all Ascomycetes suggests a frequent horizontal gene transfer between genera and a finite diversity of hybrids — also explaining their scarcity. The provided insights into relations of hybrids and other SM genes will serve in rational design of new hybrid enzymes.

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Section: Resultssupporting

confidence: 73%

Genus level analysis of PKS-NRPS and NRPS-PKS hybrids reveals their origin in Aspergilli

2019

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“…Bioautography is a technique that combines thinlayer chromatography with agar diffusion (Choma and Jesionek, 2015). Both techniques are tools for the separation of molecules at laboratory level, capable of biologically identifying which specific compounds of an extract act actively in that compound, such as the endophytic fungi extracts from several plant species that act as potent antimicrobials, since some known drugs and microorganism derivatives (Fanali et al, 2016) are already on the market as antibiotics (Luo et al, 2016), being used in the treatment of various diseases such as Alzheimer's, from bioactive (Wang et al, 2016), anticancer (Petersen et al, 2014;Zaiyou et al, 2015) and anti-allergic compounds, among others (Sakurai et al, 2003).…”

Section: Introductionmentioning

confidence: 99%

Chromatography and bioautography of endophytic fungi extracts of Uncaria tomentosa (Willd.) DC with antibacterial activity

Gonã‡Alves¹,

ARAÃšJO²,

Brasil³

et al. 2019

J. Med. Plants Res.

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Endophytic fungi of different species have already proved their efficacy against a range of pathogenic bacteria. However, the separation of the compounds contained in these extracts that actually have an effective activity is not a constant, but it is essential for the scientific knowledge to formulate a new medication. Thus, this study aimed to separate compounds from two endophytic fungi extracts of Uncaria tomentosa with positive results against Gram-positive and Gram-negative bacteria. The separation was carried out by thin-layer chromatography and bioautography. For this, it was necessary to produce fungal extracts from the endophytes Colletotrichum (23916) and Fusarium (23952), which were separated from the liquid state by filtration. The remaining filtrate was divided into ethyl acetate and then concentrated in a rotary evaporator at 40°C. Antimicrobial activity was evaluated and the Minimum Inhibitory Concentration (MIC) was determined with the following test microorganisms: Escherichia coli, Enterecoccus faecalis, Klebsiella pneumoniae and Staphylococcus aureus. Subsequently, it was carried out the thin layer chromatography (TLC) of the extracts using hexane, ethyl acetate/hexane, ethyl acetate and acetate/methanol. The reading was performed in 312 nm UV light, and right after the chromatography, the bioautography was carried out. The following Rf values were obtained: 0.30 for K. pneumoniae and 0.35 for E. coli, in ethyl acetate, for the extract 23952, and 0.81 for K. pneumoniae and 0.41 for S. aureus, in styrene acetate, for the extract 23916, confirming different compounds by bioautography. Therefore, it was concluded that several compounds present in the extracts tested have antibacterial activity.

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Non-Alkaloid Nitrogen-Containing Compounds from Fungi

Hached

Cassani

Zbiss

et al. 2023

Natural Secondary Metabolites

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Isolation, Structural Analyses and Biological Activity Assays against Chronic Lymphocytic Leukemia of Two Novel Cytochalasins — Sclerotionigrin A and B

Cited by 11 publications

References 33 publications

Genus level analysis of PKS-NRPS and NRPS-PKS hybrids reveals their origin in Aspergilli

Genus level analysis of PKS-NRPS and NRPS-PKS hybrids reveals their origin in Aspergilli

Chromatography and bioautography of endophytic fungi extracts of Uncaria tomentosa (Willd.) DC with antibacterial activity

Non-Alkaloid Nitrogen-Containing Compounds from Fungi

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