Samholides, Swinholide-Related Metabolites from a Marine Cyanobacterium cf. <i>Phormidium</i> sp.

Tao, Yiwen; Li, Pinglin; Zhang, Daojing; Glukhov, Evgenia; Gerwick, Lena; Zhang, Chen; Murray, Thomas F.; Gerwick, William H.

doi:10.1021/acs.joc.8b00028

Cited by 17 publications

(16 citation statements)

References 32 publications

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“…An alternative production method is based on the rationale that BGCs are subject to extensive horizontal gene transfer and that culturable sources therefore likely exist even for idiosyncratic compounds from deep-branching, uncultured divisions. Previous work on the serendipitous discovery of culturable bacterial producers of invertebrate polyketides [36][37][38][39] support this concept. As shown here, a targeted, BGC-based search can not only reveal such producers, but also yield novel synthetic biology chassis for previously demanding biosynthetic steps.…”

Section: Resultsmentioning

confidence: 92%

Genome mining- and synthetic biology-enabled production of hypermodified peptides

et al. 2019

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The polytheonamides are among the most complex and biosynthetically distinctive natural products known to date. These potent peptide cytotoxins are derived from a ribosomal precursor processed by 49 mostly non-canonical posttranslational modifications. Since the producer is a "microbial dark matter" bacterium only distantly related to any cultivated organism, >70-step chemical syntheses have been developed to access these unique compounds. Here we mined prokaryotic diversity to establish a synthetic platform based on the new host Microvirgula aerodenitrificans that produces hypermodified peptides within two days. Using this system, we generated the aeronamides, new polytheonamide-type compounds with near-picomolar cytotoxicity. Aeronamides, as well as the polygeonamides produced from deep-rock biosphere DNA, contain the highest numbers of D-amino acids in known biomolecules. With increasing bacterial genomes being sequenced, similar host mining strategies might become feasible to access further elusive natural products from uncultivated life.

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Section: Resultsmentioning

confidence: 92%

Genome mining- and synthetic biology-enabled production of hypermodified peptides

et al. 2019

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“…Methods for the NCI-H460 cytotoxicity assay [ 101 ] and the Griess assay [ 102 , 103 ] were adapted from the literature.…”

Section: Methodsmentioning

confidence: 99%

Applying a Chemogeographic Strategy for Natural Product Discovery from the Marine Cyanobacterium Moorena bouillonii

et al. 2020

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The tropical marine cyanobacterium Moorena bouillonii occupies a large geographic range across the Indian and Western Tropical Pacific Oceans and is a prolific producer of structurally unique and biologically active natural products. An ensemble of computational approaches, including the creation of the ORCA (Objective Relational Comparative Analysis) pipeline for flexible MS1 feature detection and multivariate analyses, were used to analyze various M. bouillonii samples. The observed chemogeographic patterns suggested the production of regionally specific natural products by M. bouillonii. Analyzing the drivers of these chemogeographic patterns allowed for the identification, targeted isolation, and structure elucidation of a regionally specific natural product, doscadenamide A (1). Analyses of MS2 fragmentation patterns further revealed this natural product to be part of an extensive family of herein annotated, proposed natural structural analogs (doscadenamides B–J, 2–10); the ensemble of structures reflect a combinatorial biosynthesis using nonribosomal peptide synthetase (NRPS) and polyketide synthase (PKS) components. Compound 1 displayed synergistic in vitro cancer cell cytotoxicity when administered with lipopolysaccharide (LPS). These discoveries illustrate the utility in leveraging chemogeographic patterns for prioritizing natural product discovery efforts.

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“…All of these samholides showed potential activities against the human lung cancer cell line H-460 with IC 50 values ranging from 170 to 910 nM. Comparison of the activities of these samholides suggested that the sugar and glycericacid units played important roles in enhancing the cytotoxic activity (Tao et al, 2018).…”

Section: Macrocyclic Lactonesmentioning

confidence: 99%

Glycosylated Natural Products From Marine Microbes

Cai

et al. 2020

Front. Chem.

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A growing body of evidence indicates that glycosylated natural products have become vital platforms for the development of many existing first-line drugs. This review covers 205 new glycosides over the last 22 years (1997-2018), from marine microbes, including bacteria, cyanobacteria, and fungi. Herein, we discuss the structures and biological activities of these compounds, as well as the details of their source organisms.

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Samholides, Swinholide-Related Metabolites from a Marine Cyanobacterium cf. Phormidium sp.

Cited by 17 publications

References 32 publications

Genome mining- and synthetic biology-enabled production of hypermodified peptides

Genome mining- and synthetic biology-enabled production of hypermodified peptides

Applying a Chemogeographic Strategy for Natural Product Discovery from the Marine Cyanobacterium Moorena bouillonii

Glycosylated Natural Products From Marine Microbes

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