Svetamycins A–G, Unusual Piperazic Acid-Containing Peptides from <i>Streptomyces</i> sp.

Dardić, Denis; Lauro, Gianluigi; Bifulco, Giuseppe; Laboudie, Patricia; Sakhaii, Peyman; Bauer, Armin; Vilcinskas, Andreas; Hammann, Peter; Plaza, Alberto

doi:10.1021/acs.joc.7b00228

Cited by 44 publications

(48 citation statements)

References 28 publications

(53 reference statements)

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“…The plates were incubated for 48 h at 37°C, shaking at 180 rpm. Cell viability was determined using the BacTiter-Glo TM assay (Promega, Mannheim, Germany) and a LUMIstar OPTIMA microplate luminometer (BMG Labtech, Ortenberg, Germany) for the readout (Dardic et al, 2017).…”

Section: Methodsmentioning

confidence: 99%

Antibiotic-Producing Beneficial Bacteria in the Gut of the Burying Beetle Nicrophorus vespilloides

et al. 2019

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The increasing prevalence of antibiotic-resistant human pathogens is a growing public concern and there is intense pressure to identify new antibacterial compounds that can be developed into antibiotics with novel mode of action. Evolutionary theory predicts that insects that have evolved to occupy sophisticated ecological niches by feeding and reproducing on carcasses will depend on their gut microbiome to prevent colonization by invading pathogens taken up with the diet. This inspired our hypothesis that the complex interactions between the core microbiome and the more flexible microbial communities dependent on the environment may promote the outsourcing of antibiotic synthesis to beneficial microbes. We tested this hypothesis by cultivating and characterizing bacteria isolated from the gut of the burying beetle Nicrophorus vespilloides , which feeds and reproduces on small vertebrate carcasses buried in the soil to avoid competitors such as fly maggots. The extracts of isolated bacteria were screened for activity against human pathogens such as Escherichia coli , Pseudomonas aeruginosa , Staphylococcus aureus , and Candida albicans . More than 400 strains were isolated, among which the crude extract of Serratia marcescens 2MH3-2 displayed promising activity against Staphylococcus aureus . Bioactivity-guided fractionation enabled purification of the primary antimicrobial compound of the extract. By LC-MS and NMR experiments, it was identified as serrawettin W2 (C 38 H 61 N 5 O 9 ), the antibacterial and nematostatic activity of which was corroborated in our study. We postulate that this antibiotic could contribute to the control of both bacteria and phoretic nematodes in the gut, which compete for food when transferred to the carcass. Our study shows that the gut microbiome of N. vespilloides is a promising resource for the screening of antibiotic-producing bacteria.

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Section: Methodsmentioning

confidence: 99%

Antibiotic-Producing Beneficial Bacteria in the Gut of the Burying Beetle Nicrophorus vespilloides

et al. 2019

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“…Other PA-containing cyclic hexapeptides contain only three PA moieties, as, for example, the svetamycins (Dardic et al 2017) or NW-G10 and NW-G11 (Wei et al 2012), two PA moieties, as, for example, depsidomycin (Isshiki et al 1990), piperastatin A þ B Murakami, Harada, Yamazaki et al 1996) or pipalamcin (Uchihata et al 2002), or only one PA moiety as in the case for marformycins (Liu et al 2015).…”

Section: Piperazic Acid Containing Peptidesmentioning

confidence: 99%

Piperazic acid containing peptides produced by an endophytic Streptomyces sp. isolated from the medicinal plant Atropa belladonna

Bekiesch

Oberhofer

Sykora

et al. 2019

Natural Product Research

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The culture broth of endophytic Streptomyces sp. AB100, isolated from the shoots of medicinal plant Atropa belladonna (L.) was investigated for the presence of antibacterial compounds. After initial testing followed by bioactivity-guided fractionation, six new piperazic acid (PA)-containing congeners of two known peptides, JBIR-39 and JBIR-40, were identified by HR-MS/MS and NMR analyses. Only the dehydroxylated hexapeptidic derivatives with unusual incorporation of four PA moieties exhibited weak antibacterial activity against Gram-positive test organism Bacillus subtilis. A 16S rDNA-based phylogenetic tree of known Streptomyces spp. producing PA-containing hexapeptides isolated from different habitats and endophyte Streptomyces AB100 showed considerable diversity, suggesting that these metabolites may play an important environmental role beyond their antibacterial activity.

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“…Piperazic acid (Piz; PubChem CID: 2762538), a cyclic hydrazine and a non‐proteinogenic amino acid, has been found in over 140 molecules of natural products, many of which exhibit promising biological activities (Ciufolini and Xi, 1998; Morgan et al ., 2019): antrimycins (Shimada et al ., 1981) and svetamycins (Dardic et al ., 2017) as tuberculostatic agents, kutznerides (Broberg et al ., 2006) as antimicrobial agents and luzopeptins as anti‐human immunodeficiency viral agents (Ohkuma et al ., 1980). Moreover, Piz has been shown to be able to induce β‐turns in peptides (Ciufolini and Xi, 1998).…”

Section: Introductionmentioning

confidence: 99%

Bioproduction of L‐piperazic acid in gram scale using Aureobasidium melanogenum

Chen

Wang

Liu

et al. 2021

Microbial Biotechnology

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Currently, piperazic acid is chemically synthesized using ecologically unfriendly processes. Microbial synthesis from glucose is an attractive alternative to chemical synthesis. In this study, we report the production of L-piperazic acid via microbial fermentation with the first engineered fungal strain of Aureobasidium melanogenum; this strain was constructed by chassis development, genetic element reconstitution and optimization, synthetic rewiring and constitutive genetic circuit reconstitution, to build a robust Lpiperazic acid synthetic cascade. These genetic modifications enable A. melanogenum to directly convert glucose to L-piperazic acid without relying on the use of either chemically synthesized precursors or harsh conditions. This bio-based process overcomes the shortcomings of the conventional synthesis routes. The ultimately engineered strain is a very high-efficient cell factory that can excrete 1.12 AE 0.05 g l -1 of L-piperazic acid after a 120-h 10.0-l fed-batch fermentation; this is the highest titre of L-piperazic acid reported using a microbial cell factory.

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Svetamycins A–G, Unusual Piperazic Acid-Containing Peptides from Streptomyces sp.

Cited by 44 publications

References 28 publications

Antibiotic-Producing Beneficial Bacteria in the Gut of the Burying Beetle Nicrophorus vespilloides

Antibiotic-Producing Beneficial Bacteria in the Gut of the Burying Beetle Nicrophorus vespilloides

Piperazic acid containing peptides produced by an endophytic Streptomyces sp. isolated from the medicinal plant Atropa belladonna

Bioproduction of L‐piperazic acid in gram scale using Aureobasidium melanogenum

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