ArticleJournal of natural products2017
Discovery of C-Glycosylpyranonaphthoquinones in Streptomyces sp. MBT76 by a Combined NMR-Based Metabolomics and Bioinformatics Workflow.
Article in Journal of natural products, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed, 43 citations in OpenAlex.
- Construction and Diversification of Natural Product Biosynthetic Gene Clusters at High Efficiency and Accuracy.ACS synthetic biology · 2025Article
- Hirocidins, Cytotoxic Metabolites from Streptomyces hiroshimensis, Induce Mitochondrion-Mediated Apoptosis.Angewandte Chemie (International ed. in English) · 2024Article
- Antimicrobial and Cytotoxic Naphthoquinones from Microbial Origin: An Updated Review.Mini reviews in medicinal chemistry · 2024Review
- Tandocyclinones A and B, Ether BridgedMarine drugs · 2023Article
- Genomic and Metabolite Profiling Reveal a NovelMicrobiology spectrum · 2023Article
- Metabolic engineering ofEngineering microbiology · 2022Review
- A single-domain small protein Med-ORF10 regulates the production of antitumour agent medermycin in Streptomyces.Microbial biotechnology · 2021Article
- Vertirhodins A-F, C-Linked Pyrrolidine-Iminosugar-Containing Pyranonaphthoquinones fromOrganic letters · 2021Article
- An Integrative Approach for the Characterization of Plant-PathogenicFrontiers in microbiology · 2021Article
- Recent Advances in Strategies for Activation and Discovery/Characterization of Cryptic Biosynthetic Gene Clusters inMicroorganisms · 2020Review
- An aberrant metabolic flow toward early shunt products in the granaticin biosynthetic machinery of Streptomyces vietnamensis GIMV4.0001.The Journal of antibiotics · 2020Article
- Bioactivity-HiTES Unveils Cryptic Antibiotics Encoded in Actinomycete Bacteria.ACS chemical biology · 2019Article
- Genome-guided and mass spectrometry investigation of natural products produced by a potential new actinobacterial strain isolated from a mangrove ecosystem in Futian, Shenzhen, China.Scientific reports · 2019Article
- Mining Actinomycetes for Novel Antibiotics in the Omics Era: Are We Ready to Exploit This New Paradigm?Antibiotics (Basel, Switzerland) · 2018Review
- Mining for Microbial Gems: Integrating Proteomics in the Postgenomic Natural Product Discovery Pipeline.Proteomics · 2018Review
- Omics based approach for biodiscovery of microbial natural products in antibiotic resistance era.Journal, genetic engineering & biotechnology · 2018Review
- Intertwined Precursor Supply during Biosynthesis of the Catecholate-Hydroxamate Siderophores Qinichelins in Streptomyces sp. MBT76.ACS chemical biology · 2017Article
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Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Mining of microbial genomes has revealed that actinomycetes harbor far more biosynthetic potential for bioactive natural products than anticipated. Activation of (cryptic) biosynthetic gene clusters and identification of the corresponding metabolites has become a focal point for drug discovery. Here, we applied NMR-based metabolomics combined with bioinformatics to identify novel C-glycosylpyranonaphthoquinones in Streptomyces sp. MBT76 and to elucidate the biosynthetic pathway. Following activation of the cryptic qin gene cluster for a type II polyketide synthase (PKS) by constitutive expression of its pathway-specific activator, bioinformatics coupled to NMR profiling facilitated the chromatographic isolation and structural elucidation of qinimycins A-C (1-3). The intriguing structural features of the qinimycins, including 8-C-glycosylation, 5,14-epoxidation, and 13-hydroxylation, distinguished these molecules from the model pyranonaphthoquinones actinorhodin, medermycin, and granaticin. Another novelty lies in the unusual fusion of a deoxyaminosugar to the pyranonaphthoquinone backbone during biosynthesis of the antibiotics BE-54238 A and B (4, 5). Qinimycins showed weak antimicrobial activity against Gram-positive bacteria. Our work shows the utility of combining bioinformatics, targeted activation of cryptic gene clusters, and NMR-based metabolic profiling as an effective pipeline for the discovery of microbial natural products with distinctive skeletons.
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