ArticleJournal of the American Chemical Society2014
Mining soil metagenomes to better understand the evolution of natural product structural diversity: pentangular polyphenols as a case study.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed, 60 citations in OpenAlex.
- Bioactive Angucyclines/Angucyclinones Discovered from 1965 to 2023.Marine drugs · 2025Review
- Metagenomic study of lake microbial mats reveals protease-inhibiting antiviral peptides from a core microbiome member.Proceedings of the National Academy of Sciences of the United States of America · 2024Article
- Enantioselective Transfer Hydrogenative Cycloaddition Unlocks the Total Synthesis of SF2446 B3: An Aglycone of Arenimycin and SF2446 Type II Polyketide Antibiotics.Journal of the American Chemical Society · 2023Article
- Cloning and Expression of Metagenomic DNA in Streptomyces lividans and Its Subsequent Fermentation for Optimized Production.Methods in molecular biology (Clifton, N.J.) · 2023Article
- Article
- SelectiveJournal of medicinal chemistry · 2022Article
- Genetic and Biochemical Characterization of Halogenation and Drug Transportation Genes Encoded in the Albofungin Biosynthetic Gene Cluster.Applied and environmental microbiology · 2022Article
- Combined assembly of long and short sequencing reads improve the efficiency of exploring the soil metagenome.BMC genomics · 2022Article
- A Natural Product Chemist's Guide to Unlocking Silent Biosynthetic Gene Clusters.Annual review of biochemistry · 2021Review
- Metathramycin, a new bioactive aureolic acid discovered by heterologous expression of a metagenome derived biosynthetic pathway.RSC chemical biology · 2021Article
- Discovery of Novel Biosynthetic Gene Cluster Diversity From a Soil Metagenomic Library.Frontiers in microbiology · 2020Article
- Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction.Journal of the American Chemical Society · 2018Article
- Discovery of the Tyrobetaine Natural Products and Their Biosynthetic Gene Cluster via Metabologenomics.ACS chemical biology · 2018Article
- Unique amalgamation of primary and secondary structural elements transform peptaibols into potent bioactive cell-penetrating peptides.Proceedings of the National Academy of Sciences of the United States of America · 2017Article
- Sampling Terrestrial Environments for Bacterial Polyketides.Molecules (Basel, Switzerland) · 2017Review
- Phylogeny-guided (meta)genome mining approach for the targeted discovery of new microbial natural products.Journal of industrial microbiology & biotechnology · 2017Review
- New insights into bacterial type II polyketide biosynthesis.F1000Research · 2017Review
- Genome-based survey of nonribosomal peptide synthetase and polyketide synthase gene clusters in type strains of the genus Microtetraspora.The Journal of antibiotics · 2016Article
- Saccharomyces cerevisiae as a tool for mining, studying and engineering fungal polyketide synthases.Fungal genetics and biology : FG & B · 2016Review
- Culture-independent discovery of natural products from soil metagenomes.Journal of industrial microbiology & biotechnology · 2016Review
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Sequence-guided mining of metagenomic libraries provides a means of recovering specific natural product gene clusters of interest from the environment. In this study, we use ketosynthase gene (KS) PCR amplicon sequences (sequence tags) to explore the structural and biosynthetic diversities of pentangular polyphenols (PP). In phylogenetic analyses, eDNA-derived sequence tags often fall between closely related clades that are associated with gene clusters known to encode distinct chemotypes. We show that these common "intermediate" sequence tags are useful for guiding the discovery of not only novel bioactive metabolites but also collections of closely related gene clusters that can provide new insights into the evolution of natural product structural diversity. Gene clusters corresponding to two eDNA-derived KSβ sequence tags that reside between well-defined KSβ clades associated with the biosynthesis of (C24)-pradimicin and (C26)-xantholipin type metabolites were recovered from archived soil eDNA libraries. Heterologous expression of these gene clusters in Streptomyces albus led to the isolation of three new PPs (compounds 1-3). Calixanthomycin A (1) shows potent antiproliferative activity against HCT-116 cells, whereas arenimycins C (2) and D (3) display potent antibacterial activity. By comparing genotypes and chemotypes across all known PP gene clusters, we define four PP subfamilies, and also observe that the horizontal transfer of PP tailoring genes has likely been restricted to gene clusters that encode closely related chemical structures, suggesting that only a fraction of the "natural product-like" chemical space that can theoretically be encoded by these secondary metabolite tailoring genes has likely been sampled naturally.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.