Peptaibiotics: Harnessing the potential of microbial secondary metabolites for mitigation of plant pathogens

Pereira-Dias, Leandro; Oliveira-Pinto, Paulo R.; Fernandes, Juliana Oliveira; Regalado, Laura; Mendes, Rafael J.; Teixeira, Cátia; Mariz-Ponte, Nuno; Gomes, Paula; Santos, Conceição

doi:10.1016/j.biotechadv.2023.108223

Cited by 7 publications

(3 citation statements)

References 161 publications

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“…Peptaibols make up a group of peptide natural products (PNPs) synthesized by filamentous fungi, with prominent producers belonging to the Trichoderma , Stilbella , and Paecilomyces genera. These PNPs typically consist of 5–22 amino acid (AA) residues, rich in noncanonical α,α-dialkylated α-amino acids, such as α-aminoisobutyric acid (Aib) and isovaline (Iva), and feature an N-terminal acyl substituent and a C-terminal amino alcohol moiety. , These structural characteristics of peptaibols facilitate the formation of their distinctive helical structures and contribute to their diverse biological functions, which encompass antibacterial, antifungal, antiviral, and cytotoxic activities. − However, the herbicidal potential of fungal peptaibols remains underexplored to date.…”

Section: Introductionmentioning

confidence: 99%

Isolation, Characterization, and Bioherbicidal Potential of the 16-Residue Peptaibols from Emericellopsis sp. XJ1056

Song,

Ai,

Zhou

et al. 2024

J. Agric. Food Chem.

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Eco-friendly bioherbicides are urgently needed for managing the problematic weed Amaranthus retroflexus. A mass spectrometry-and bioassay-guided screening approach was employed to identify phytotoxic secondary metabolites from fungi for the development of such bioherbicides. This effort led to the discovery of six phytotoxic 16-residue peptaibols, including five new compounds (2−6) and a known congener (1), from Emericellopsis sp. XJ1056. Their planar structures were elucidated through the analysis of tandem mass and NMR spectroscopic data. The absolute configurations of the chiral amino acids were determined by advanced Marfey's method and chiral-phase liquid chromatography-mass spectrometry (LC-MS) analysis. Bioinformatic analysis and targeted gene disruption identified the biosynthetic gene cluster for these peptaibols. Compounds 1 and 2 significantly inhibited the radicle growth of A. retroflexus seedlings, and 1 demonstrated potent postemergence herbicidal activity against A. retroflexus while exhibiting minimal toxicity to Sorghum bicolor. Structure−activity relationship analysis underscored the importance of trans-4hydroxy-L-prolines at both the 10th and 13th positions for the herbicidal activities of these peptaibols.

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Section: Introductionmentioning

confidence: 99%

Isolation, Characterization, and Bioherbicidal Potential of the 16-Residue Peptaibols from Emericellopsis sp. XJ1056

Song,

Ai,

Zhou

et al. 2024

J. Agric. Food Chem.

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“…Peptide natural products form the basis of many important molecules including agrochemicals (Cane et al, 1998;Pereira-Dias et al, 2023), bioproducts (Tao et al, 2023), and therapeutics (Corpuz et al, 2022;Girija et al, 2022). Of these applications, the most historically significant one has been as an important source for drug leads (Atanasov et al, 2015;Harvey et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

Cell-free protein synthesis for nonribosomal peptide synthetic biology

Sword,

Abbas,

Bailey

2024

Front. Nat. Prod.

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Peptide natural products have a wide range of useful applications as pesticides, veterinary agents, pharmaceuticals, and bioproducts. To discover new natural products, manipulate them for analog generation, and to harness the potential of these bioactive compounds for synthetic biology, it is necessary to develop robust methods for the expression of biosynthetic genes. Cell-free synthetic biology is emerging as an important complementary approach because it is highly desirable to express protein on a more rapid timescale and does not rely upon the genetic tractability of a strain thus improving the throughput of design-build-test-learn cycles. Additionally, generating metabolites outside the cell can overcome issues such as cellular toxicity which can hamper applications like antibiotic development. In this review, we focus on the cell-free production of peptide natural products generated by non-ribosomal peptide synthetase. Nonribsomal peptides are biosynthesized by non-ribosomal peptide synthetases which are large “mega” enzymes that provide specific challenges to heterologous expression. First, we summarize NRPSs and their corresponding peptide metabolites that are expressed in cell-free systems. With that, we discuss the requirements and challenges to express such large proteins in cell-free protein synthesis as well as host machineries that have been developed for cell-free protein synthesis that could be particularly relevant to generating non-ribosomal peptide metabolites in the future. The development of cell-free systems can then be used for prototyping to accelerate efforts towards engineered biosynthesis of these complex pathways.

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“…Peptaibols are linear peptides typically with 5–21 amino acid residues that are characterized by the presence of nonproteinogenic amino acids, an acylated N-terminus, and a C-terminus that has been reduced to a 2-amino alcohol. , Very lipophilic peptaibols with a long-chain acyl group at the N-terminus are called lipopeptaibols. Peptaibols are known to be produced by several genera of soil-borne and plant pathogenic fungi, especially Trichoderma , but also Acremonium , Chlonostachys , Emericellopsis , and Tolypocladium , among others. ,− Peptaibols are best known for their antibacterial properties; however some have also been shown to have other bioactivities including antifungal, neuroleptic, and cytotoxic activities .…”

mentioning

confidence: 99%

Cytotoxic Peptaibols from Trichoderma strigosum

Park,

Kim,

Deyrup

et al. 2024

J. Nat. Prod.

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Five new lipopeptaibols (1−5) and eight new 19residue peptaibols (8−15) along with two known lipopeptaibols, lipovelutibols C (6) and D (7) were isolated from Trichoderma strigosum. The planar structures of the newly discovered peptaibols (1−5, 8−15) were elucidated using 1D and 2D NMR, and UPLC-MS/MS data. The absolute configurations for new peptaibols (1− 5, 8−15) were elucidated using the advanced Marfey's method and GITC (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate) derivatization. Through analysis of CD spectra, these peptabols were found to have right-handed helical conformations. While most of the new compounds were significantly more active than the positive control, 9, 10, 12, and 15 containing Ser and Leu at positions 10 and 11, respectively, were the most cytotoxic against MDA-MB-231, SNU449, SKOV3, DU145, and HCT116 cancer cell lines, and the 19-residue peptaibols were generally more potent than lipopeptaibols.

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Peptaibiotics: Harnessing the potential of microbial secondary metabolites for mitigation of plant pathogens

Cited by 7 publications

References 161 publications

Isolation, Characterization, and Bioherbicidal Potential of the 16-Residue Peptaibols from Emericellopsis sp. XJ1056

Isolation, Characterization, and Bioherbicidal Potential of the 16-Residue Peptaibols from Emericellopsis sp. XJ1056

Cell-free protein synthesis for nonribosomal peptide synthetic biology

Cytotoxic Peptaibols from Trichoderma strigosum

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