Biosynthesis of pyrrolnitrin and other phenylpyrrole derivatives by bacteria (up to mid-1999)

Pée, K.-H. Van; Ligón, James M.

doi:10.1039/a902138h

Cited by 94 publications

(54 citation statements)

References 59 publications

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“…Compound 3 has a 2,3-dihydropyrrole moiety, and an analogous compound, albeit with a fully unsaturated pyrrole ring, was postulated as an intermediate in the biosynthesis of compound 1 (21,37). Thus, banegasine may be an intermediate in, or a by-product of, the biosynthesis of pyrrolnitrin by strain 679-2.…”

Section: Discussionmentioning

confidence: 99%

“…The antimicrobial (1,37) and phytotoxic (35) activities, respectively, of pyrrolnitrin and maculosin have been described previously. Compound 1 is produced by a wide variety of bacteria, including the pseudomonads (1,23), Enterobacter agglomerans (13), Burkholderia cepacia (19), and others (37). To the best of our knowledge, compound 2 has not been isolated from a prokaryote, nor has it been produced in combination with compound 1 by any organism.…”

Section: Discussionmentioning

confidence: 99%

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Synergistic Antimicrobial Activity of Metabolites Produced by a Nonobligate Bacterial Predator

Cain

Lee²,

Waldo

et al. 2003

Antimicrob Agents Chemother

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A naturally occurring, gram-negative, nonobligate predator bacterial strain 679-2, exhibits broad-spectrum antimicrobial activity that is due, in part, to the production of three extracellular compounds. Antimicrobialactivity-directed fractionation of a culture of strain 679-2 against a panel of microorganisms has led to the isolation of three compounds: pyrrolnitrin, maculosin, and a new compound, which we have named banegasine. Although pyrrolnitrin is well known in the literature, it has not been found in cells with the herbicide maculosin. Further, this is the first report of production of maculosin by a prokaryote. Both maculosin and banegasine, which displayed no antimicrobial activities alone, were found to potentiate the antimicrobial activity of pyrrolnitrin. Based on 16S rRNA sequence, cellular fatty acid composition, and biochemical and cultural characteristics, strain 679-2 appears to represent a new genus and species of eubacteria, Aristabacter necator. The potent, broad-spectrum antimicrobial activity of predator strain 679-2 may be due to synergism between metabolites.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Synergistic Antimicrobial Activity of Metabolites Produced by a Nonobligate Bacterial Predator

Cain

Lee²,

Waldo

et al. 2003

Antimicrob Agents Chemother

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“…In many symbiotic associations between bacteria and eukaryotes, the former produce secondary metabolites that protect their host from pathogens or display other beneficial effects. Pyrrolnitrin, which is produced by PfA, the nonfood source symbiont of D. discoideum, has potent antifungal activity against a variety of soil-borne fungi (20); it is also known to play a crucial role in other symbiotic associations between the producer P. fluorescens strain and plants. The decreased susceptibility of an infected host to soil-borne pathogens can be used as a form of biocontrol, and fluorescent pseudomonads play an important role as biocontrol agents (21)(22)(23)(24).…”

Section: Differential Effect Of Pyrrolnitrin On Farmer and Nonfarmermentioning

confidence: 99%

A bacterial symbiont is converted from an inedible producer of beneficial molecules into food by a single mutation in the gacA gene

Stallforth

Brock

Cantley

et al. 2013

Proc. Natl. Acad. Sci. U.S.A.

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Stable multipartite mutualistic associations require that all partners benefit. We show that a single mutational step is sufficient to turn a symbiotic bacterium from an inedible but host-beneficial secondary metabolite producer into a host food source. The bacteria's host is a "farmer" clone of the social amoeba Dictyostelium discoideum that carries and disperses bacteria during its spore stage. Associated with the farmer are two strains of Pseudomonas fluorescens, only one of which serves as a food source. The other strain produces diffusible small molecules: pyrrolnitrin, a known antifungal agent, and a chromene that potently enhances the farmer's spore production and depresses a nonfarmer's spore production. Genome sequence and phylogenetic analyses identify a derived point mutation in the food strain that generates a premature stop codon in a global activator (gacA), encoding the response regulator of a twocomponent regulatory system. Generation of a knockout mutant of this regulatory gene in the nonfood bacterial strain altered its secondary metabolite profile to match that of the food strain, and also, independently, converted it into a food source. These results suggest that a single mutation in an inedible ancestral strain that served a protective role converted it to a "domesticated" food source.symbiosis | GacA-GacS two-component system | differential metabolomics S mall molecules regulate mutually beneficial associations between bacterial symbionts and their eukaryotic hosts. A fascinating set of structurally diverse molecules that defend the host, initiate host developmental changes, and carry out other important functions have been shaped by their evolutionary history (1-10). Recently, Brock et al. (11) described an association between the social amoeba Dictyostelium discoideum and a variety of Gram-negative bacteria, some of which it carries to initiate new food populations.D. discoideum is a popular model for studying multicellularity, chemical signaling, general eukaryotic cellular mechanisms, and social phenomena (12-15). The protist is typically found in soil, where it preys on bacteria; in nutrient-rich environments it lives as single-celled organisms that reproduce by binary fission. Upon starvation, cAMP-mediated aggregation occurs, leading to the formation of a multicellular pseudoplasmodium containing up to 10 5 individual cells. Eventually, the aggregate develops into a fruiting body in which some 20% of the cells differentiate into a dead stalk that supports a spherical structure known as the sorus; the latter contains 80% of the cells that turn into spores.Previous work by Brock et al. (11) showed that about one-third of wild-collected clones of D. discoideum engage in stable associations with bacteria throughout the sporulation and dispersal process. These clones are called "primitive farmers" because they carry, seed, and prudently harvest their bacterial food.Schultz and Brady (16) characterized agriculture as a specialized form of symbiosis known in only four animal groups: humans,...

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“…The other notable exception is pyrrolnitrin, which was licensed shortly after its discovery from Pseudomonas pyrrocinia for the treatment for fungal infections of the skin. 42 It also served as a lead structure for synthesis of several more light-stable analogues, fenpiclonil 16 and fludioxonil, which are presently in use as agrochemical fungicides. Interestingly, pyrrolnitrin is one of the few myxobacterial natural products to have a structure identical to a compound produced by other bacterial groups, including Serratia sp.…”

Section: Anti-fungalmentioning

confidence: 99%

Myxobacterial secondary metabolites: bioactivities and modes-of-action

2010

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The myxobacteria, long a source of fascination due to their sophisticated, social lifestyles, are now increasingly recognized as multi-producers of promising natural products. Here we provide an overview of the bioactivities and modes-of-action of these secondary metabolites, with an emphasis on potential clinical applications. Highlights of metabolite modes-of-action: case studies 3.1 Soraphen: an inhibitor of acetyl-CoA carboxylase 3.2 Corallopyronin, myxopyronin, ripostatin, and sorangicin: inhibitors of bacterial RNA polymerase 3.3 Disorazol: a potential anti-cancer agent 3.4 Argyrin: a proteasome inhibitor 4 Outlook 5 Acknowledgements 6 References

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Biosynthesis of pyrrolnitrin and other phenylpyrrole derivatives by bacteria (up to mid-1999)

Cited by 94 publications

References 59 publications

Synergistic Antimicrobial Activity of Metabolites Produced by a Nonobligate Bacterial Predator

Synergistic Antimicrobial Activity of Metabolites Produced by a Nonobligate Bacterial Predator

A bacterial symbiont is converted from an inedible producer of beneficial molecules into food by a single mutation in the gacA gene

Myxobacterial secondary metabolites: bioactivities and modes-of-action

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