Antibiotic Activity of a Paraphaeosphaeria sporulosa-Produced Diketopiperazine against Salmonella enterica

Carrieri, Raffaele; Borriello, Giorgia; Piccirillo, Giulio; Lahoz, E.; Sorrentino, R.; Cermola, Michele; Censi, Sergio Bolletti; Grauso, Laura; Mangoni, Alfonso; Vinale, Francesco

doi:10.3390/jof6020083

Cited by 12 publications

(8 citation statements)

References 29 publications

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“…The diketopiperazine cyclo(L-Pro-L-Phe) (104, Figure 7), was purified from Paraphaeosphaeria sporulosa, associated with Fragaria x ananassa. Compound 104 displayed activity against Salmonella strains, S1 and S2, with IC 50 values of 7.2 and 7.9 µg/mL and MICs of 71.3 and 78.6 µg/mL, respectively [63].…”

Section: Minor Taxa Of the Ascomycetesmentioning

confidence: 99%

Fungal Endophytes: A Potential Source of Antibacterial Compounds

Deshmukh

Dufossé²,

Chhipa

et al. 2022

JoF

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Antibiotic resistance is becoming a burning issue due to the frequent use of antibiotics for curing common bacterial infections, indicating that we are running out of effective antibiotics. This has been more obvious during recent corona pandemics. Similarly, enhancement of antimicrobial resistance (AMR) is strengthening the pathogenicity and virulence of infectious microbes. Endophytes have shown expression of various new many bioactive compounds with significant biological activities. Specifically, in endophytic fungi, bioactive metabolites with unique skeletons have been identified which could be helpful in the prevention of increasing antimicrobial resistance. The major classes of metabolites reported include anthraquinone, sesquiterpenoid, chromone, xanthone, phenols, quinones, quinolone, piperazine, coumarins and cyclic peptides. In the present review, we reported 451 bioactive metabolites isolated from various groups of endophytic fungi from January 2015 to April 2021 along with their antibacterial profiling, chemical structures and mode of action. In addition, we also discussed various methods including epigenetic modifications, co-culture, and OSMAC to induce silent gene clusters for the production of noble bioactive compounds in endophytic fungi.

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Section: Minor Taxa Of the Ascomycetesmentioning

confidence: 99%

Fungal Endophytes: A Potential Source of Antibacterial Compounds

Deshmukh

Dufossé²,

Chhipa

et al. 2022

JoF

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“…The identified cyclic dipeptides belong to the class of Proline–Xaa cyclodipeptides (Xaa denotes unspecified amino acids). These molecules have been reported from various fungal genera and have phytotoxic (compounds 1 , 2 , and 3 ) or antifungal (compound 2 and 4 ) activity (see Wang et al, 2017 for review; Carrieri et al, 2020 ). Additionally, compounds 2 and 3 have been identified from the culture filtrate of endophytic Epichloë typhina ( Song et al, 2015 ; Zhou et al, 2015 ) and have been reported to show antifungal activity ( Wang et al, 1999 ; Magnusson et al, 2003 ).…”

Section: Discussionmentioning

confidence: 99%

Revision of the genus Aciculosporium (Clavicipitaceae) with a description of a new species on wavyleaf basketgrass, and proline-containing cyclic dipeptide production by A. take

et al. 2021

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The genus Aciculosporium (Clavicipitaceae, Hypocreales, Ascomycota) was established in 1908 for A. take, which is the causal fungus of witches' broom of bamboo. Although the original description was valid at that time, a type specimen for A. take has not been designated. To standardize the use of this genus and species name, a neotypification and reference specimen of A. take are proposed. Multilocus phylogenetic analyses based on DNA sequences from 28S rDNA, TEF, Tub2, Mcm7, and RPB2 revealed that A. sasicola is from a different lineage to A. take, and other specimens from wavyleaf basket grass (Oplismenus undulatifolius) represent a distinct species proposed here as Aciculosporium oplismeni sp. nov. Chemical analysis using mass spectrometry and nuclear magnetic resonance spectroscopy showed that A. take produces four proline-containing cyclic dipeptides, which are moieties of ergot alkaloids. However, ergot alkaloids, lolines, peramine, indole-diterpenes, and lolitrem were not detected in the culture solvent. This study offers clarification of the lineage and morphology of this genus.

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“…The cytotoxicity of cyclic dipeptides was evaluated against VERO cell line (African Green Monkey kidney cell line), and no cytotoxicity was recorded for concentrations up to 100 µg/mL [202,221]. Among antibacterial agents, DKP alkaloid-actinozine A, cyclo(2-OH-Pro-L-Leu), but also cyclo(2-OH-D-Pro-L-Leu), cyclo(D-Pro-L-Phe), and cyclo(L-Pro-L-Phe) can be mentioned as well [222,223].…”

Section: Antibacterial Activitymentioning

confidence: 99%

Cyclic Dipeptides: The Biological and Structural Landscape with Special Focus on the Anti-Cancer Proline-Based Scaffold

et al. 2021

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Cyclic dipeptides, also know as diketopiperazines (DKP), the simplest cyclic forms of peptides widespread in nature, are unsurpassed in their structural and bio-functional diversity. DKPs, especially those containing proline, due to their unique features such as, inter alia, extra-rigid conformation, high resistance to enzyme degradation, increased cell permeability, and expandable ability to bind a diverse of targets with better affinity, have emerged in the last years as biologically pre-validated platforms for the drug discovery. Recent advances have revealed their enormous potential in the development of next-generation theranostics, smart delivery systems, and biomaterials. Here, we present an updated review on the biological and structural profile of these appealing biomolecules, with a particular emphasis on those with anticancer properties, since cancers are the main cause of death all over the world. Additionally, we provide a consideration on supramolecular structuring and synthons, based on the proline-based DKP privileged scaffold, for inspiration in the design of compound libraries in search of ideal ligands, innovative self-assembled nanomaterials, and bio-functional architectures.

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Antibiotic Activity of a Paraphaeosphaeria sporulosa-Produced Diketopiperazine against Salmonella enterica

Cited by 12 publications

References 29 publications

Fungal Endophytes: A Potential Source of Antibacterial Compounds

Fungal Endophytes: A Potential Source of Antibacterial Compounds

Revision of the genus <i>Aciculosporium </i>(<i>Clavicipitaceae</i>) with a description of a new species on wavyleaf basketgrass, and proline-containing cyclic dipeptide production by <i>A. take</i>

Cyclic Dipeptides: The Biological and Structural Landscape with Special Focus on the Anti-Cancer Proline-Based Scaffold

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