Aurachin SS, a new antibiotic from Streptomyces sp. NA04227

Zhang, Mei; Yang, Cheng; Xiao, Yong; Zhang, Bo; Deng, Xin Zhao; Yang, Li; Shi, Jing; Wang, Yi Shuang; Li, Wei; Jiao, Rui Hua; Tan, Ren Xiang; Ge, Hui

doi:10.1038/ja.2017.50

Cited by 22 publications

(17 citation statements)

References 17 publications

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“…Keyicin was active against gram-positive Bacillus subtilis with a MIC of 7.97 mg/L and against MRSA with a MIC of 2.01 mg/L. Zhang et al (2017) obtained MICs of 1.39–5.57 mg/L for two compounds from the Aurachin family that had antimicrobial activity against S. aureus , Streptococcus pyogenes , and B. subtilis . They obtained a MIC of 44.57 mg/L against MRSA, whereas rifampicin and ampicillin had respective MICs of 3.29 and 22.36 mg/L.…”

Section: Resultsmentioning

confidence: 96%

Balsacone C, a New Antibiotic Targeting Bacterial Cell Membranes, Inhibits Clinical Isolates of Methicillin-Resistant Staphylococcus aureus (MRSA) Without Inducing Resistance

et al. 2019

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New options are urgently needed for the treatment of methicillin-resistant Staphylococcus aureus (MRSA) infections. Balsacone C is a new dihydrochalcone extracted from Populus balsamifera that has been reported previously as being active against Staphylococcus aureus. Here, we evaluate the antibacterial activity of balsacone C against MRSA. Thirty-four (34) MRSA isolates were obtained from hospitalized patients; these isolates were then characterized for their resistance. Most of these MRSA (>85%) were resistant to penicillin, amoxicillin/clavulanic acid, ciprofloxacin, moxifloxacin, levofloxacin, clindamycin, erythromycin, and cefoxitin as well as being sensitive to linezolid, trimethoprim/sulfamethoxazole, rifampicin, and gentamicin. When tested against all MRSA isolates and various gram-positive bacteria, the antibacterial activity of balsacone C produced a MIC of 3–11.6 mg/mL. We observed no resistant isolates of MRSA (against balsacone C) even after 30 passages. Microscopy fluorescence showed that bacteria cell membrane integrity was compromised by low concentrations of balsacone C. Scanning electron microscope (SEM) confirmed balsacone C–provoked changes in the bacterial cell membrane and we find a dose-dependent release of DNA and proteins. This loss of cellular integrity leads to cell death and suggests a low potential for the development of spontaneous resistance.

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Section: Resultsmentioning

confidence: 96%

Balsacone C, a New Antibiotic Targeting Bacterial Cell Membranes, Inhibits Clinical Isolates of Methicillin-Resistant Staphylococcus aureus (MRSA) Without Inducing Resistance

et al. 2019

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“…NA04227. 12 Stable isotope enrichment studies with 13 C- and 18 O-labeled precursors revealed that the quinoline and quinolone cores in 4 – 7 were synthesized from anthranilic acid and acetate, 10 suggesting the involvement of a polyketide synthase.…”

Section: Results and Discussionmentioning

confidence: 99%

“…Characterization of the aua , 13 rau , 11 and sau ( 12 ) clusters responsible for the biosynthesis of 4 – 7 , 8 , and 9 , respectively, revealed the following set of core genes shared between the three clusters: a prenyltransferase, an acyl carrier protein (ACP), two β-ketoacyl-ACP synthases, and a benzoate:CoA ligase ( Figure 5 ). The presence of two β-ketoacyl-ACP synthases and an ACP in all three clusters further supported that a type II polyketide synthase (PKS) was involved in the assembly of the aurachin core.…”

Section: Results and Discussionmentioning

confidence: 99%

Marinoterpins A–C: Rare Linear Merosesterterpenoids from Marine-Derived Actinomycete Bacteria of the Family Streptomycetaceae

et al. 2021

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The chemical examination of two undescribed marine actinobacteria has yielded three rare merosesterterpenoids, marinoterpins A–C ( 1 – 3 , respectively). These compounds were isolated from the culture broth extracts of two marine-derived actinomycetes associated with the family Streptomycetaceae, (our strains were CNQ-253 and AJS-327). The structures of the new compounds were determined by extensive interpretation of 1D and 2D NMR, MS, and combined spectroscopic data. These compounds represent new chemical motifs, combining quinoline- N -oxides with a linear sesterterpenoid side chain. Additionally, consistent in all three metabolites is the rare occurrence of two five-ring ethers, which were derived from an apparent cyclization of methyl group carbons to adjacent hydroxy-bearing methylene groups in the sesterterpenoid side chain. Genome scanning of AJS-327 allowed for the identification of the marinoterpin ( mrt ) biosynthetic cluster, which consists of 16 open-reading frames that code for a sesterterpene pyrophosphate synthase, prenyltransferase, type II polyketide synthase, anthranilate:CoA-ligase, and several tailoring enzymes apparently responsible for installing the N -oxide and bis-tetrahydrofuran ring motifs.

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“…Another class of structurally distinct prenylated quinolones are the quinolone-type aurachins, which are substituted by isoprenoid chains at the C-3 position (Table A2), and have been reported from Stigmatella, Rhodococcus, and Streptomyces species [34][35][36][37]. These are unique in that they are the Another class of structurally distinct prenylated quinolones are the quinolone-type aurachins, which are substituted by isoprenoid chains at the C-3 position (Table A2), and have been reported from Stigmatella, Rhodococcus, and Streptomyces species [34][35][36][37]. These are unique in that they are the only reported bacterial 4-quinolones to possess alkyl chains larger than a methyl group at the C-3 position.…”

Section: Structural Diversity and Distributionmentioning

confidence: 99%

“…Acta 2259 displayed low to moderate activity against S. epidermidis, B. subtilis and P. acnes, respectively [34][35][36]. The O-methylated aurachin SS (ASS10), isolated from a Streptomyces strain, possessed reduced antimicrobial activity compared to aurachins C and D, though it is unclear whether this is due to the presence of the methoxy group, or the shortened side-chain [37].…”

Section: Antibacterial Activitymentioning

confidence: 99%

Bacterial Alkyl-4-quinolones: Discovery, Structural Diversity and Biological Properties

2020

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The alkyl-4-quinolones (AQs) are a class of metabolites produced primarily by members of the Pseudomonas and Burkholderia genera, consisting of a 4-quinolone core substituted by a range of pendant groups, most commonly at the C-2 position. The history of this class of compounds dates back to the 1940s, when a range of alkylquinolones with notable antibiotic properties were first isolated from Pseudomonas aeruginosa. More recently, it was discovered that an alkylquinolone derivative, the Pseudomonas Quinolone Signal (PQS) plays a key role in bacterial communication and quorum sensing in Pseudomonas aeruginosa. Many of the best-studied examples contain simple hydrocarbon side-chains, but more recent studies have revealed a wide range of structurally diverse examples from multiple bacterial genera, including those with aromatic, isoprenoid, or sulfur-containing side-chains. In addition to their well-known antimicrobial properties, alkylquinolones have been reported with antimalarial, antifungal, antialgal, and antioxidant properties. Here we review the structural diversity and biological activity of these intriguing metabolites.

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Aurachin SS, a new antibiotic from Streptomyces sp. NA04227

Cited by 22 publications

References 17 publications

Balsacone C, a New Antibiotic Targeting Bacterial Cell Membranes, Inhibits Clinical Isolates of Methicillin-Resistant Staphylococcus aureus (MRSA) Without Inducing Resistance

Balsacone C, a New Antibiotic Targeting Bacterial Cell Membranes, Inhibits Clinical Isolates of Methicillin-Resistant Staphylococcus aureus (MRSA) Without Inducing Resistance

Marinoterpins A–C: Rare Linear Merosesterterpenoids from Marine-Derived Actinomycete Bacteria of the Family Streptomycetaceae

Bacterial Alkyl-4-quinolones: Discovery, Structural Diversity and Biological Properties

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