Pigments of Pseudomonas species. Part I. Structure and synthesis of aeruginosin A

Holliman, F. G.

doi:10.1039/j39690002514

Cited by 26 publications

(38 citation statements)

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“…Unfortunately, we were unable to identify this material by C 18 reverse-phase HPLC because the pigment is extremely hydrophilic and could not be extracted with the solvents commonly used to recover phenazines. These properties are similar to those of the aeruginosins described previously by Herbert and Holliman (27) and Holliman (28). We hypothesize that the dark red pigment synthesized by P. aeruginosa PAOmxS mutants and by E. coli expressing phzM is not a complex of aeruginosins A and B but rather is a colored intermediate (probably 5-methylphenazine-1-carboxylic acid betaine) formed through methylation of PCA by PhzM.…”

Section: Discussionsupporting

confidence: 64%

Functional Analysis of Genes for Biosynthesis of Pyocyanin and Phenazine-1-Carboxamide from Pseudomonas aeruginosa PAO1

et al. 2001

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Two seven-gene phenazine biosynthetic loci were cloned from Pseudomonas aeruginosa PAO1. The operons, designated phzA1B1C1D1E1F1G1 and phzA2B2C2D2E2F2G2, are homologous to previously studied phenazine biosynthetic operons from Pseudomonas fluorescens and Pseudomonas aureofaciens. Functional studies of phenazine-nonproducing strains of fluorescent pseudomonads indicated that each of the biosynthetic operons from P. aeruginosa is sufficient for production of a single compound, phenazine-1-carboxylic acid (PCA). Subsequent conversion of PCA to pyocyanin is mediated in P. aeruginosa by two novel phenazine-modifying genes, phzM and phzS, which encode putative phenazine-specific methyltransferase and flavin-containing monooxygenase, respectively. Expression of phzS alone in Escherichia coli or in enzymes, pyocyanin-nonproducing P. fluorescens resulted in conversion of PCA to 1-hydroxyphenazine. P. aeruginosa with insertionally inactivated phzM or phzS developed pyocyanin-deficient phenotypes. A third phenazine-modifying gene, phzH, which has a homologue in Pseudomonas chlororaphis, also was identified and was shown to control synthesis of phenazine-1-carboxamide from PCA in P. aeruginosa PAO1. Our results suggest that there is a complex pyocyanin biosynthetic pathway in P. aeruginosa consisting of two core loci responsible for synthesis of PCA and three additional genes encoding unique enzymes involved in the conversion of PCA to pyocyanin, 1-hydroxyphenazine, and phenazine-1-carboxamide.Phenazine compounds produced by fluorescent Pseudomonas species are biologically active metabolites that function in microbial competitiveness (37), the suppression of soilborne plant pathogens (1,11,55,56), and virulence in human and animal hosts (35).The most widely studied phenazine-producing fluorescent pseudomonad is P. aeruginosa, a gram-negative opportunistic pathogen of animals, insects, nematodes, and plants (30,33,35,46). In humans, P. aeruginosa infects immunocompromised, burned, or injured patients and can cause both acute and chronic lung disease. Strains of P. aeruginosa produce a variety of redox-active phenazine compounds, including pyocyanin, phenazine-1-carboxylic acid (PCA), 1-hydroxyphenazine (1-OH-PHZ), and phenazine-1-carboxamide (PCN) (7,52,57).From 90 to 95% of P. aeruginosa isolates produce pyocyanin (52), and the presence of high concentrations of pyocyanin in the sputum of cystic fibrosis patients has suggested that this compound plays a role in pulmonary tissue damage observed with chronic lung infections (64). This idea is supported by several recent studies which demonstrated that pyocyanin contributes in a variety of ways to the pathophysiological effects observed in airways infected by P. aeruginosa. Pyocyanin interferes with the regulation of ion transport, ciliary beat frequency, and mucus secretion in airway epithelial cells by altering the cytosolic concentration of calcium (15). It may interact with endothelium-derived relaxing factor or with nitric oxide (which plays a central role in the control ...

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Section: Discussionsupporting

confidence: 64%

Functional Analysis of Genes for Biosynthesis of Pyocyanin and Phenazine-1-Carboxamide from Pseudomonas aeruginosa PAO1

et al. 2001

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“…The aeruginosin-containing eluates were concentrated under reduced pressure. The UV-visible spectra of both compounds corresponded to those previously reported (15,20).…”

Section: Vol 75 2009supporting

confidence: 51%

“…Aeruginosins A and B were recovered as water-soluble red pigments from 6-day supernatants from P. aeruginosa PA14 cultures grown in Holliman's medium (20). Approximately 200 ml of the culture supernatant was applied to chromatographic columns.…”

Section: Vol 75 2009mentioning

confidence: 99%

“…In addition, P. aeruginosa can produce two red pigments, aeruginosins A and B (5-methyl-7-amino-1-carboxymethylphenazinium betaine and 5-methyl-7-amino-1-carboxy-3-sulfo-methylphenazinium betaine, respectively), after prolonged incubation. Unlike the other phenazines produced by P. aeruginosa, aeruginosins A and B are highly water soluble, and their biological activities are much less well characterized (15,20).…”

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confidence: 99%

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Pseudomonas aeruginosa - Candida albicans Interactions: Localization and Fungal Toxicity of a Phenazine Derivative

Gibson

Sood

Hogan

2009

Appl Environ Microbiol

191

186

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Phenazines are redox-active small molecules that play significant roles in the interactions between pseudomonads and diverse eukaryotes, including fungi. When Pseudomonas aeruginosa and Candida albicans were cocultured on solid medium, a red pigmentation developed that was dependent on P. aeruginosa phenazine biosynthetic genes. Through a genetic screen in combination with biochemical experiments, it was found that a P. aeruginosa-produced precursor to pyocyanin, proposed to be 5-methyl-phenazinium-1-carboxylate (5MPCA), was necessary for the formation of the red pigmentation. The 5MPCA-derived pigment was found to accumulate exclusively within fungal cells, where it retained the ability to be reversibly oxidized and reduced, and its detection correlated with decreased fungal viability. Pyocyanin was not required for pigment formation or fungal killing. Spectral analyses showed that the partially purified pigment from within the fungus differed from aeruginosins A and B, two red phenazine derivatives formed late in P. aeruginosa cultures. The red pigment isolated from C. albicans that had been cocultured with P. aeruginosa was heterogeneous and difficult to release from fungal cells, suggesting its modification within the fungus. These findings suggest that intracellular targeting of some phenazines may contribute to their toxicity and that this strategy could be useful in developing new antifungals.

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“…Relatively little antibiotic was produced in the broth cultures used to measure phenazine production (Table 4). Qualitative and quantitative differences in phenazine production as a function of growth conditions, including aeration, have been reported previously for pseudomonads (17,20,26). Mutant times in experiment 4.…”

Section: Methodsmentioning

confidence: 97%

Role of a phenazine antibiotic from Pseudomonas fluorescens in biological control of Gaeumannomyces graminis var. tritici

1988

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Pseudomonasfluorescens 2-79 (NRRL B-15132) and its rifampin-resistant derivative 2-79RN10 are suppressive to take-all, a major root disease of wheat caused by Gaeumannomyces graminis var. tritici. Strain 2-79 produces the antibiotic phenazine-l-carboxylate, which is active in vitro against G. graminis var. tritici and other fungal root pathogens. Mutants defective in phenazine synthesis (Phz-) were generated by TnS insertion and then compared with the parental strain to determine the importance of the antibiotic in take-all suppression on wheat roots. Six independent, prototrophic Phz-mutants were noninhibitory to G. graminis var. tritici in vitro and provided significantly less control of take-all than strain 2-79 on wheat seedlings. Antibiotic synthesis, fungal inhibition in vitro, and suppression of take-all on wheat were coordinately restored in two mutants complemented with cloned DNA from a 2-79 genomic library. These mutants contained TnS insertions in adjacent EcoRI fragments in the 2-79 genome, and the restriction maps of the region flanking the insertions and the complementary DNA were colinear. These results indicate that sequences required for phenazine production were present in the cloned DNA and support the importance of the phenazine antibiotic in disease suppression in the rhizosphere.

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Pigments of Pseudomonas species. Part I. Structure and synthesis of aeruginosin A

Cited by 26 publications

References 0 publications

Functional Analysis of Genes for Biosynthesis of Pyocyanin and Phenazine-1-Carboxamide from Pseudomonas aeruginosa PAO1

Functional Analysis of Genes for Biosynthesis of Pyocyanin and Phenazine-1-Carboxamide from Pseudomonas aeruginosa PAO1

Pseudomonas aeruginosa - Candida albicans Interactions: Localization and Fungal Toxicity of a Phenazine Derivative

Role of a phenazine antibiotic from Pseudomonas fluorescens in biological control of Gaeumannomyces graminis var. tritici

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