Isolation, NMR spectroscopy, and conformational analysis of the antibiotic ina 2770 (cineromycin B) produced by Streptomyces strain

Терехова, Л. П.; Galatenko, O. A.; Kulyaeva, V. V.; Malkina, N. D.; Boikova, Yu. V.; Катруха, Г. С.; Shashkov, Alexander S.; Gerbst, Alexey G.; Nifantiev, Nikolay E.

doi:10.1007/s11172-007-0121-1

Cited by 7 publications

(6 citation statements)

References 4 publications

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“…) is a 14‐membered macrolide antibiotic that has gained attention for having activity against methicillin‐resistant Staphylococcus aureus (MRSA). To better understand the solution structure of cinermycin B, Terekhova et al conducted NMR spectroscopy experiments to measure NOEs and J‐coupling constants, and performed structural modeling using the MM3 molecular mechanics potential . The lowest‐energy structure of cineromycin B was found to have a different conformation than the one suggested by the experimental data.…”

Section: Resultsmentioning

confidence: 99%

Bayesian inference of conformational state populations from computational models and sparse experimental observables

Voelz

Zhou

2014

J. Comput. Chem.

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We present a Bayesian inference approach to estimating conformational state populations from a combination of molecular modeling and sparse experimental data. Unlike alternative approaches, our method is designed for use with small molecules and emphasizes high-resolution structural models, using inferential structure determination with reference potentials, and Markov Chain Monte Carlo to sample the posterior distribution of conformational states. As an application of the method, we determine solution-state conformational populations of the 14-membered macrocycle cineromycin B, using a combination of previously published sparse Nuclear Magnetic Resonance (NMR) observables and replica-exchange molecular dynamic/Quantum Mechanical (QM)-refined conformational ensembles. Our results agree better with experimental data compared to previous modeling efforts. Bayes factors are calculated to quantify the consistency of computational modeling with experiment, and the relative importance of reference potentials and other model parameters.

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Section: Resultsmentioning

confidence: 99%

Bayesian inference of conformational state populations from computational models and sparse experimental observables

Voelz

Zhou

2014

J. Comput. Chem.

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“…This molecule was reported to have antibacterial activity against Gram-positive bacteria and Candida albicans [ 19 ]. *cineromycin B [ 13 , 22 , 23 ] ( 3 ) and 2,3-dihydrocineromycin B [ 13 , 24 ] ( 4 ). These two active molecules have been already described from Streptomyces species, as two 14-membered ring macrolide antibiotics.…”

Section: Resultsmentioning

confidence: 99%

“… Cineromycin B ( 3 ), lit. [ 23 ] δ C δ H δ C δ H 1 166.1 – 166.3 – 2 115.1 5.87 (d, 15.5) 115.0 5.86 (d, 16) 3 155.2 6.93 (d, 15.5) 155.5 6.91 (d, 16) 4 73.4 – 73.4 – 5 135.2 5.87 (d, 15.5) 135.3 5.85 (d, 16) 6 133.6 5.73 (dd, 16.3, 4.8) 133.6 5.71 (dd, 16, 5) 7 74.6 4.55 (m) 74.5 4.53 (d, 5) 8 137.9 – 137.9 – 9 129.5 5.23 (m) 129.4 5.21 (brm) 10 25.1 2.10 (m), 1.80 (m) 25.0 2.10 (brm), 1.84 (d, 16.5) 11 34.8 1.21 (m), 1.16(m) 34.3 1.22 (m), 1.17 (m) 12 39.5 1.25 (m) 39.5 1.40 (brq, 6) 13 75.5 4.55 (m) 75.6 4.55 (d, 7) CH 3 -4 27.1 1.55 (s) 27.0 …”

Section: Methodsmentioning

confidence: 99%

Bioactive Secondary Metabolites from a New Terrestrial Streptomyces sp. TN262

Elleuch

Shaaban

Smaoui

et al. 2009

Appl Biochem Biotechnol

101

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During our search for Streptomyces spp. as new producers of bioactive secondary metabolites, the ethyl acetate extract of the new terrestrial Streptomyces isolate TN262 delivered eight antimicrobially active compounds. They were identified as 1-acetyl-β-carboline (1), tryptophol (2), cineromycin B (3), 2,3-dihydrocineromycin B (4), cyclo-(tyrosylprolyl) (5), 3-(hydroxyacetyl)-indole (6), brevianamide F (7), and cis-cyclo-(l-prolyl-l-leucyl) (8). Three further metabolites were detected in the unpolar fractions using GC–MS and tentatively assigned as benzophenone (9), N-butyl-benzenesulfonamide (10), and hexanedioic acid-bis-(2-ethylhexyl) ester (11). This last compound is known as plasticizer derivatives, but it has never been described from natural sources. In this article, we describe the identification of the new Streptomyces sp. isolate TN262 using its cultural characteristics, the nucleotide sequence of the corresponding 16S rRNA gene and the phylogenetic analysis, followed by optimization, large-scale fermentation, isolation of the bioactive constituents, and determination of their structures. The biological activity of compounds (2), (3), (4), and those of the unpolar fractions was addressed as well.

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“…The formula C32H48N6O9 was dereplicated as the peptide actinoramide B, which was detected in a marine bacterium highly corelated to the genus Streptomyces [35]. Likewise, the formula C17H26O4 was dereplicated as cineromycin-B antibiotic that showed significant MRSA inhibition, which was isolated from the actinomycetales strain INA 2770 [36]. The formula C19H27N5O7 was annotated as heterobactin B, a siderophore discovered from Rhodococcus erythropolis IGTS8 [37], while the formula C26H39NO5 was dereplicated as piericidin-F, which was reported from Streptomyces sp.…”

Section: Metabolomics Analysis Of the Coculture Extract Of Actinokinementioning

confidence: 99%

Bio-Guided Isolation of Antimalarial Metabolites from the Coculture of Two Red Sea Sponge-Derived Actinokineospora and Rhodococcus spp.

et al. 2021

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Coculture is a productive technique to trigger microbes’ biosynthetic capacity by mimicking the natural habitats’ features principally by competition for food and space and interspecies cross-talks. Mixed cultivation of two Red Sea-derived actinobacteria, Actinokineospora spheciospongiae strain EG49 and Rhodococcus sp. UR59, resulted in the induction of several non-traced metabolites in their axenic cultures, which were detected using LC–HRMS metabolomics analysis. Antimalarial guided isolation of the cocultured fermentation led to the isolation of the angucyclines actinosporins E (1), H (2), G (3), tetragulol (5) and the anthraquinone capillasterquinone B (6), which were not reported under axenic conditions. Interestingly, actinosporins were previously induced when the axenic culture of the Actinokineospora spheciospongiae strain EG49 was treated with signalling molecule N-acetyl-d-glucosamine (GluNAc); this finding confirmed the effectiveness of coculture in the discovery of microbial metabolites yet to be discovered in the axenic fermentation with the potential that could be comparable to adding chemical signalling molecules in the fermentation flask. The isolated angucycline and anthraquinone compounds exhibited in vitro antimalarial activity and good biding affinity against lysyl-tRNA synthetase (PfKRS1), highlighting their potential developability as new antimalarial structural motif.

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Isolation, NMR spectroscopy, and conformational analysis of the antibiotic ina 2770 (cineromycin B) produced by Streptomyces strain

Cited by 7 publications

References 4 publications

Bayesian inference of conformational state populations from computational models and sparse experimental observables

Bayesian inference of conformational state populations from computational models and sparse experimental observables

Bioactive Secondary Metabolites from a New Terrestrial Streptomyces sp. TN262

Bio-Guided Isolation of Antimalarial Metabolites from the Coculture of Two Red Sea Sponge-Derived Actinokineospora and Rhodococcus spp.

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