Pigments of Pseudomonas species. Part II. Structure of aeruginosin B

Herbert, Richard B.; Holliman, F. G.

doi:10.1039/j39690002517

Cited by 18 publications

(21 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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“…5B) but lacked the maximum at ϳ390 nm, which is characteristic of red P. aeruginosa phenazines aeruginosins A (Fig. 5B) and B (not shown), as reported previously by Holliman et al (15,20). The spectrum of the red pigment isolated from fungal cells also differed from those of other known P. aeruginosa phenazines, including PCA, pyocyanin, and the products of PhzM activity on PCA produced in E. coli (Fig.…”

Section: Resultsmentioning

confidence: 56%

“…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 2009mentioning

confidence: 49%

“…The purification of the pigment is described in more detail in Results. The approximate concentration of the red pigment was determined using the extinction coefficient for aeruginosins A and B (15,20). The absorbance and fluorescence spectra were obtained using Treatment of yeast with the PhzM product.…”

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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Thermospray mass spectrometric analysis of phenazines

Watson

Taylor

Wilson

et al. 1988

Biol. Mass Spectrom.

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Positive and negative thermospray mass spectra have been recorded for a number of phenazines at the sub microgram level. The spectra are dominated by molecular ion species (IM + HI', [M -HI-) with minimal fragmentation. The gas chromatographic/electron impact mass spectrometric behaviour of the phenazines was also investigated. A number of phenazines were not amenable to gas chromatographic/mass spectrometric analysis without derivatization; in contrast, thermospray mass spectrometric data were obtained for each phenazine. Thermospray liquid chromatography/mass spectrometry has been applied to identify phenazine-l-carboxylic acid and 2-hydroxyphenazine in culture filtrates of Pseudomonas aureofaciens and 1-amidophenazine from Pseudomonas aeruginosa.

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Pigments of Pseudomonas species. Part II. Structure of aeruginosin B

Cited by 18 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

Thermospray mass spectrometric analysis of phenazines

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