Sequences of Acretocins, Peptaibiotics Containing the Rare 1‐Aminocyclopropanecarboxylic Acid, from <i>Acremonium crotocinigenum</i> CBS 217.70

Brückner, Hans; Fox, S. W.; Degenkolb, Thomas

doi:10.1002/cbdv.201900276

Cited by 6 publications

(5 citation statements)

References 55 publications

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“…Fungal peptaibols have attracted intensive attention from both the scientific community and the pharmaceutical industry since the discovery of alamethicin in the late 1960s from the biocontrol fungus Trichoderma viride [32][33][34][35]. Many described peptaibols are reported to have an antifungal effect, but most of them possessed activity against plant pathogenic fungi [35][36][37][38][39]. In recent years, there have been a few reports addressing the activity of peptaibols against clinically important fungi [21,40,41].…”

Section: Discussionmentioning

confidence: 99%

The Emericellipsins A–E from an Alkalophilic Fungus Emericellopsis alkalina Show Potent Activity against Multidrug-Resistant Pathogenic Fungi

Куварина¹,

Gavryushina²,

Kul'ko

et al. 2021

JoF

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Novel antimicrobial peptides with antifungal and cytotoxic activity were derived from the alkalophilic fungus Emericellopsis alkalina VKPM F1428. We previously reported that this strain produced emericellipsin A (EmiA), which has strong antifungal and cytotoxic properties. Further analyses of the metabolites obtained under a special alkaline medium resulted in the isolation of four new homologous (Emi B–E). In this work, we report the complete primary structure and detailed biological activity for the newly synthesized nonribosomal antimicrobial peptides called emericellipsins B–E. The inhibitory activity of themajor compound, EmiA, against drug-resistant pathogenic fungi was similar to that of amphotericin B (AmpB). At the same time, EmiA had no hemolytic activity towards human erythrocytes. In addition, EmiA demonstrated low cytotoxic activity towards the normal HPF line, but possessed cancer selectivity to the K-562 and HCT-116 cell lines. Emericillipsins from the alkalophilic fungus Emericellopsis alkaline are promising treatment alternatives to licensed antifungal drugs for invasive mycosis therapy, especially for multidrug-resistant aspergillosis and cryptococcosis.

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Section: Discussionmentioning

confidence: 99%

The Emericellipsins A–E from an Alkalophilic Fungus Emericellopsis alkalina Show Potent Activity against Multidrug-Resistant Pathogenic Fungi

Куварина¹,

Gavryushina²,

Kul'ko

et al. 2021

JoF

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“…Fragmentation of the [M + 2H] 2+ ion at m / z 893.5827 resulted in a series of observable b/y fragments, in accordance with the sequential loss of amino acid residues from the N- and C- termini, respectively. Interestingly, formation of specific pairs of b/y fragments derived from the α-cleavage of β-Ala ions were greatly suppressed or absent, a feature common in other peptaibiotics containing β-Ala residues [ 28 , 29 ], which further supported the existence and positions of the β-Ala units in the proposed amino acid sequence.…”

Section: Resultsmentioning

confidence: 60%

Sphaerostilbellins, New Antimicrobial Aminolipopeptide Peptaibiotics from Sphaerostilbella toxica

et al. 2020

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Sphaerostilbella toxica is a mycoparasitic fungus that can be found parasitizing wood-decay basidiomycetes in the southern USA. Organic solvent extracts of fermented strains of S. toxica exhibited potent antimicrobial activity, including potent growth inhibition of human pathogenic yeasts Candida albicans and Cryptococcus neoformans, the respiratory pathogenic fungus Aspergillus fumigatus, and the Gram-positive bacterium Staphylococcus aureus. Bioassay-guided separations led to the purification and structure elucidation of new peptaibiotics designated as sphaerostilbellins A and B. Their structures were established mainly by analysis of NMR and HRMS data, verification of amino acid composition by Marfey’s method, and by comparison with published data of known compounds. They incorporate intriguing structural features, including an N-terminal 2-methyl-3-oxo-tetradecanoyl (MOTDA) residue and a C-terminal putrescine residue. The minimal inhibitory concentrations for sphaerostilbellins A and B were measured as 2 μM each for C. neoformans, 1 μM each for A. fumigatus, and 4 and 2 μM, respectively, for C. albicans. Murine macrophage cells were unaffected at these concentrations.

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“…A previous study has shown that ChoCl supplementation of N. crassa growth medium led to the increased expression of the 1-aminocyclopropane-1-carboxylate (ACC) deaminase, which mediates the formation of ACC ( Martins et al, 2013 ). In some fungi, the presence of ACC has been linked to the peptaibiotics neofrapeptins and acretocins, isolated from Geotrichum candidum SID 22780 and Acremonium crotocinigenum cultures, respectively ( Fredenhagen et al, 2006 ; Brückner et al, 2019 ). Peptaibiotics show a unique structure varying from 5 to 21 amino acid residues, including numerous NPAAs, mainly α-aminoisobutyric acid (Aib), and/or lipoamino acids ( Degenkolb et al, 2003 ; Degenkolb and Brückner, 2008 ).…”

Section: Resultsmentioning

confidence: 99%

Untargeted Metabolomics Sheds Light on the Secondary Metabolism of Fungi Triggered by Choline-Based Ionic Liquids

et al. 2022

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Fungal secondary metabolites constitute a rich source of yet undiscovered bioactive compounds. Their production is often silent under standard laboratory conditions, but the production of some compounds can be triggered simply by altering the cultivation conditions. The usage of an organic salt – ionic liquid – as growth medium supplement can greatly impact the biosynthesis of secondary metabolites, leading to higher diversity of compounds accumulating extracellularly. This study examines if such supplements, specifically cholinium-based ionic liquids, can support the discovery of bioactive secondary metabolites across three model species: Neurospora crassa, Aspergillus nidulans, and Aspergillus fumigatus. Enriched organic extracts obtained from medium supernatant revealed high diversity in metabolites. The supplementation led apparently to increased levels of either 1-aminocyclopropane-1-carboxylate or α-aminoisobutyric acid. The extracts where bioactive against two major foodborne bacterial strains: Staphylococcus aureus and Escherichia coli. In particular, those retrieved from N. crassa cultures showed greater bactericidal potential compared to control extracts derived from non-supplemented cultures. An untargeted mass spectrometry analysis using the Global Natural Product Social Molecular Networking tool enabled to capture the chemical diversity driven by the ionic liquid stimuli. Diverse macrolides, among other compounds, were putatively associated with A. fumigatus; whereas an unexpected richness of cyclic (depsi)peptides with N. crassa. Further studies are required to understand if the identified peptides are the major players of the bioactivity of N. crassa extracts, and to decode their biosynthesis pathways as well.

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Sequences of Acretocins, Peptaibiotics Containing the Rare 1‐Aminocyclopropanecarboxylic Acid, from Acremonium crotocinigenum CBS 217.70

Cited by 6 publications

References 55 publications

The Emericellipsins A–E from an Alkalophilic Fungus Emericellopsis alkalina Show Potent Activity against Multidrug-Resistant Pathogenic Fungi

The Emericellipsins A–E from an Alkalophilic Fungus Emericellopsis alkalina Show Potent Activity against Multidrug-Resistant Pathogenic Fungi

Sphaerostilbellins, New Antimicrobial Aminolipopeptide Peptaibiotics from Sphaerostilbella toxica

Untargeted Metabolomics Sheds Light on the Secondary Metabolism of Fungi Triggered by Choline-Based Ionic Liquids

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