Nicrophorusamides A and B, Antibacterial Chlorinated Cyclic Peptides from a Gut Bacterium of the Carrion Beetle <i>Nicrophorus concolor</i>

Shin, Yern-Hyerk; Bae, Suhyun; Sim, Jaehoon; Hur, Joonseong; Jo, Shin-Il; Shin, Jongheon; Suh, Young‐Ger; Oh, Ki‐Bong; Oh, Dong‐Chan

doi:10.1021/acs.jnatprod.7b00506

Cited by 25 publications

(23 citation statements)

References 21 publications

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“…Subsequent chemical investigations of insect-associated actinomycetes have revealed that a Streptomyces strain found in the gut of a mealworm ( Tenebrio molitor ) produces lydiamycin A, an antitubercular cyclic peptide, and the pentaminomycin family of autophagy-inducing cyclic peptides. , Actinobacterial communities associated with carrion beetles have also produced multiple nonproteinogenic amino acid-bearing NRPs, such as antibacterial nicrophorusamides including 5-chloro-tryptophan and β-hydroxyasparagine from Microbacterium sp. found in the gut of Nicrophorus concolor and antitubercular coprisamides containing β-methylaspartic acid and 2,3-diaminopropanoic acid isolated from Micromonospora sp. found on Silpha perforata , which demonstrate their capability to produce structurally unique NRPs.…”

Section: Introductionmentioning

confidence: 99%

Azetidine-Bearing Non-Ribosomal Peptides, Bonnevillamides D and E, Isolated from a Carrion Beetle-Associated Actinomycete

et al. 2021

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Two new nonribosomal peptides, bonnevillamides D and E (1 and 2), have been discovered in Streptomyces sp. UTZ13 isolated from the carrion beetle, Nicrophorus concolor. Combinational analysis of the UV, MS, and NMR spectroscopic data revealed that their planar structures were comprised of dichlorinated linear peptides containing nonproteinogenic amino acid residues, such as 4methylazetidinecarboxylic acid and 4-O-acetyl-5-methylproline. The configurations of bonnevillamides D and E (1 and 2) were determined based on ROESY correlations, the advanced Marfey's method, phenylglycine methyl ester derivatization, molecular modeling, and circular dichroism spectroscopy. The nonribosomal peptide synthetase biosynthetic pathway of bonnevillamides D and E has been proposed using bioinformatic analysis of the whole-genome sequence data of Streptomyces sp. UTZ13. Their biological activity toward the aggregation of amyloid-β, which is one of the key pathogenic proteins in Alzheimer's disease, was evaluated using a thioflavin T assay and gel electrophoresis. Bonnevillamides D and E reversed the fibril formation by inducing the monomerization of amyloid-β aggregates.

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Section: Introductionmentioning

confidence: 99%

Azetidine-Bearing Non-Ribosomal Peptides, Bonnevillamides D and E, Isolated from a Carrion Beetle-Associated Actinomycete

et al. 2021

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“…In particular, insects are assumed to actively associate with chemically prolific actinobacteria, which generally originate from the soil. Indeed, studying the metabolites of insect-associated actinomycetes led to the discovery of the new cyclic depsipeptide dentigerumycin [4], a geldanamycin analog natalamycin [5], the polyketide alkaloid camporidine A [6], N-acetylcysteamine-bearing indanone thioester formicin A [7], and chlorinated cyclic peptides, nicrophorusamides [8]. These bacterial secondary metabolites display antifungal, anti-inflammatory, anticancer, and antibacterial activities.…”

Section: Introductionmentioning

confidence: 99%

Pentaminomycins C–E: Cyclic Pentapeptides as Autophagy Inducers from a Mealworm Beetle Gut Bacterium

Hwang

Jo³

et al. 2020

Microorganisms

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Pentaminomycins C–E (1–3) were isolated from the culture of the Streptomyces sp. GG23 strain from the guts of the mealworm beetle, Tenebrio molitor. The structures of the pentaminomycins were determined to be cyclic pentapeptides containing a modified amino acid, N5-hydroxyarginine, based on 1D and 2D NMR and mass spectroscopic analyses. The absolute configurations of the amino acid residues were assigned using Marfey’s method and bioinformatics analysis of their nonribosomal peptide biosynthetic gene cluster (BGC). Detailed analysis of the BGC enabled us to propose that the structural variations in 1–3 originate from the low specificity of the adenylation domain in the nonribosomal peptide synthetase (NRPS) module 1, and indicate that macrocyclization can be catalyzed noncanonically by penicillin binding protein (PBP)-type TE. Furthermore, pentaminomycins C and D (1 and 2) showed significant autophagy-inducing activities and were cytoprotective against oxidative stress in vitro.

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“…[31][32][33][34][35][36][37][38][39] Therefore, we monitored all available Burkholderia endosymbionts of R. microsporus strains from highly diverse geographic regions aroundt he globe [5] for heptarhizin production( Figure 3A and B). [31][32][33][34][35][36][37][38][39] Therefore, we monitored all available Burkholderia endosymbionts of R. microsporus strains from highly diverse geographic regions aroundt he globe [5] for heptarhizin production( Figure 3A and B).…”

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confidence: 99%

Genomics‐Driven Discovery of a Symbiont‐Specific Cyclopeptide from Bacteria Residing in the Rice Seedling Blight Fungus

et al. 2018

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The rice seedling blight fungus Rhizopus microsporus harbors endosymbiotic bacteria (Burkholderia rhizoxinica) that produce the virulence factor rhizoxin and control host development. Genome mining indicated a massive inventory of cryptic nonribosomal peptide synthetase (NRPS) genes, which have not yet been linked to any natural products. The discovery and full characterization of a novel cyclopeptide from endofungal bacteria is reported. In silico analysis of an orphan, symbiont-specific NRPS predicted the structure of a nonribosomal peptide, which was targeted by LC-MS/MS profiling of wild-type and engineered null mutants. NMR spectroscopy and chemical derivatization elucidated the structure of the bacterial cyclopeptide. Phylogenetic analyses revealed the relationship of starter C domains for rare N-acetyl-capped peptides. Heptarhizin is produced under symbiotic conditions in geographically constrained strains from the Pacific clade; this indicates a potential ecological role of the peptide.

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Nicrophorusamides A and B, Antibacterial Chlorinated Cyclic Peptides from a Gut Bacterium of the Carrion Beetle Nicrophorus concolor

Cited by 25 publications

References 21 publications

Azetidine-Bearing Non-Ribosomal Peptides, Bonnevillamides D and E, Isolated from a Carrion Beetle-Associated Actinomycete

Azetidine-Bearing Non-Ribosomal Peptides, Bonnevillamides D and E, Isolated from a Carrion Beetle-Associated Actinomycete

Pentaminomycins C–E: Cyclic Pentapeptides as Autophagy Inducers from a Mealworm Beetle Gut Bacterium

Genomics‐Driven Discovery of a Symbiont‐Specific Cyclopeptide from Bacteria Residing in the Rice Seedling Blight Fungus

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