Crystallomycin revisited after 60 years: aspartocins B and C

Tyurin, Anton P.; Alferova, Vera A.; Paramonov, Alexander S.; Shuvalov, Maxim V.; Маланичева, И. А.; Grammatikova, Natalia E.; Solyev, Pavel N.; Liu, Shaowei; Sun, Cheng‐Hang; Prokhorenko, Igor A.; Ефименко, Т. А.; Терехова, Л. П.; Efremenkova, Olga V.; Шенкарев, Захар О.; Korshun, Vladimir A.

doi:10.1039/c8md00002f

Cited by 5 publications

(8 citation statements)

References 18 publications

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“…For example, mutations that lead to a change in the composition and organization of membrane lipids would require a high energetic cost for the defending microorganism, with the variety in peptide sequences reducing cleavage by proteases [80] . Characterised LPs with antimicrobial activity include crystallomycin [81] , aspartocin [82] , laspartomycin [83] , friulimicin [84] , daptomycin [30] and surfactin [29] . However, the specific mechanisms behind these antimicrobial bioactivities remain largely unknown.…”

Section: Antimicrobial Role Of Lipopeptidesmentioning

confidence: 99%

The ecological roles of microbial lipopeptides: Where are we going?

Gutiérrez-Chávez

Benaud

Ferrari

2021

Computational and Structural Biotechnology Journal

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Lipopeptides (LPs) are secondary metabolites produced by a diversity of bacteria and fungi. Their unique chemical structure comprises both a peptide and a lipid moiety. LPs are of major biotechnological interest owing to their emulsification, antitumor, immunomodulatory, and antimicrobial activities. To date, these versatile compounds have been applied across multiple industries, from pharmaceuticals through to food processing, cosmetics, agriculture, heavy metal, and hydrocarbon bioremediation. The variety of LP structures and the diversity of the environments from which LP-producing microorganisms have been isolated suggest important functions in their natural environment. However, our understanding of the ecological role of LPs is limited. In this review, the mode of action and the role of LPs in motility, antimicrobial activity, heavy metals removal and biofilm formation are addressed. We include discussion on the need to characterise LPs from a diversity of microorganisms, with a focus on taxa inhabiting ‘extreme’ environments. We introduce the use of computational target fishing and molecular dynamics simulations as powerful tools to investigate the process of interaction between LPs and cell membranes. Together, these advances will provide new understanding of the mechanism of action of novel LPs, providing greater insights into the roles of LPs in the natural environment.

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Section: Antimicrobial Role Of Lipopeptidesmentioning

confidence: 99%

The ecological roles of microbial lipopeptides: Where are we going?

Gutiérrez-Chávez

Benaud

Ferrari

2021

Computational and Structural Biotechnology Journal

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“…Further, S. griseorubens possesses antibacterial activity against Pseudomonas aeruginosa, S. aureus, Escherichia coli, S. pneumoniae, and Bacillus subtilis (Al-Askar et al, 2014). A recent report described two lipocyclopeptide antibiotic compounds produced via non-ribosomal polypeptide synthetase (NRPS) biosynthetic gene cluster (BGC) in Streptomyces griseorubens strain INA 00887 (Tyurin et al, 2018). These antibiotics, namely, cryst-1 (Aspartocin B and C) and cryst-2 (Aspartocin A), are two major components of crystallomycin complex, an antibiotic discovered 60 years ago when advanced analytical tools were not available to fully characterize the compounds (Tyurin et al, 2018).…”

Section: S Rrna Gene Sequence Of Isolate Dsd069mentioning

confidence: 99%

“…A recent report described two lipocyclopeptide antibiotic compounds produced via non-ribosomal polypeptide synthetase (NRPS) biosynthetic gene cluster (BGC) in Streptomyces griseorubens strain INA 00887 (Tyurin et al, 2018). These antibiotics, namely, cryst-1 (Aspartocin B and C) and cryst-2 (Aspartocin A), are two major components of crystallomycin complex, an antibiotic discovered 60 years ago when advanced analytical tools were not available to fully characterize the compounds (Tyurin et al, 2018). Although S. griseorubens is known to be terrestrial, a S. griseorubens strain was previously isolated from marine sediments collected from the seabed in Weihai, China (Ye et al, 2009).…”

Section: S Rrna Gene Sequence Of Isolate Dsd069mentioning

confidence: 99%

Anthracycline Shunt Metabolites From Philippine Marine Sediment-Derived Streptomyces Destroy Cell Membrane Integrity of Multidrug-Resistant Staphylococcus aureus

et al. 2020

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The rise of antibiotic resistance (ABR) and the drying up of the pipeline for the development of new antibiotics demands an urgent search for new antibiotic leads. While the majority of clinically available antibiotics were discovered from terrestrial Streptomyces, related species from marine sediments as a source of antibiotics remain underexplored. Here, we utilized culture-dependent isolation of thirty-five marine sediment-derived actinobacterial isolates followed by a screening of their antibacterial activity against multidrug-resistant S. aureus ATCC BAA-44. Our results revealed that the crude extract of Streptomyces griseorubens strain DSD069 isolated from marine sediments collected in Romblon, Philippines displays the highest antibacterial activity, with 96.4% growth inhibition. The S. aureus ATCC BAA-44 cells treated with crude extract of Streptomyces griseorubens strain DSD069 showed cell membrane damage as demonstrated by (a) leakage and loss of vital cell constituents, including DNA and proteins, (b) irregular shrinkage of cells, and (c) increase membrane permeability. The antibiotic compounds were identified as Bisanhydroaklavinone and 1-Hydroxybisanhydroaklavinone with MIC value of 6.25 µg/mL and 50.00 µg/mL, respectively. Bisanhydroaklavinone and 1-Hydroxybisanhydroaklavinone are shunt metabolites in the biosynthesis of anticancer anthracycline derivatives namely doxorubicin, daunorubicin, and cinerubins. It is rare, however, that shunt metabolites are accumulated during fermentation of marine sediment-derived Streptomyces strain without genetic modification. Thus, our study provides evidence that natural bacterial strain can produce Bisanhydroaklavinone and 1-Hydroxybisanhydroaklavinone as antibiotic leads to combat ABR.

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“…20 In the years following, a myriad of similar or identical compounds have been reported under different names, which has led to significant confusion in the nomenclature associated with the class. 24,25,45,46 The reader is referred to a comprehensive 2005 review by Baltz and coworkers that serves to clarify much of the ambiguity associated with this group of CDAs. 21,24 Typically these lipopeptides are subdivided into three subclasses, the amphomycins, the friulimicins and the laspartomycins.…”

Section: Clinically Used Cdas and Compounds In Advanced Developmentmentioning

confidence: 99%