Petrobactin Sulfonate, a New Siderophore Produced by the Marine Bacterium Marinobacter hydrocarbonoclasticus

Hickford, Sarah J. H.; Küpper, Frithjof C.; Zhang, Guangping; Carrano, Carl J.; Blunt, John W.; Butler, Alison

doi:10.1021/np049823i

Cited by 68 publications

(63 citation statements)

References 20 publications

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“…To our knowledge, ABC transporters of sulfonated siderophores have not been characterized. However, members of the Marinobacter genus have been shown to synthesize a sulfonated siderophore (36,37). It is possible that CD2992-2989 has specificity for a sulfonated derivative of a siderophore.…”

Section: Discussionmentioning

confidence: 99%

Ferric Uptake Regulator Fur Control of Putative Iron Acquisition Systems in Clostridium difficile

Ellermeier

2015

J Bacteriol

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Clostridium difficile is an anaerobic, Gram-positive, spore-forming opportunistic pathogen and is the most common cause of hospital-acquired infectious diarrhea. Although iron acquisition in the host is a key to survival of bacterial pathogens, high levels of intracellular iron can increase oxidative damage. Therefore, expression of iron acquisition mechanisms is tightly controlled by transcriptional regulators. We identified a C. difficile homologue of the master bacterial iron regulator Fur. Using targetron mutagenesis, we generated a fur insertion mutant of C. difficile. To identify the genes regulated by Fur in C. difficile, we used microarray analysis to compare transcriptional differences between the fur mutant and the wild type when grown in highiron medium. The fur mutant had increased expression of greater than 70 transcriptional units. Using quantitative reverse transcriptase PCR (qRT-PCR), we analyzed several of the Fur-regulated genes identified by the microarray and verified that they are both iron and Fur regulated in C. difficile. Among those Fur-and iron-repressed genes were C. difficile genes encoding 7 putative cation transport systems of different classes. We found that Fur was able to bind the DNA upstream of three Fur-repressed genes in electrophoretic mobility shift assays. We also demonstrate that expression of Fur-regulated putative iron acquisition systems was increased during C. difficile infection using the hamster model. Our data suggest that C. difficile expresses multiple iron transport mechanisms in response iron depletion in vitro and in vivo. IMPORTANCEClostridium difficile is the most common cause of hospital-acquired infectious diarrhea and has been recently classified as an "urgent" antibiotic resistance threat by the CDC. To survive and cause disease, most bacterial pathogens must acquire the essential enzymatic cofactor iron. While import of adequate iron is essential for most bacterial growth, excess intracellular iron can lead to extensive oxidative damage. Thus, bacteria must regulate iron import to maintain iron homeostasis. We demonstrate here that C. difficile regulates expression of several putative iron acquisition systems using the transcriptional regulator Fur. These import mechanisms are induced under iron-limiting conditions in vitro and during C. difficile infection of the host. This suggests that during a C. difficile infection, iron availability is limited in vivo.A lmost all living organisms require iron as a cofactor for essential metabolic chemistry (1). Although iron is one of the most abundant of Earth's elements, ferric iron has very limited solubility in aqueous, nonacidic, or oxygenated environments (1). Ferric iron is most often found as iron oxides or hydroxides, which cannot be used by most organisms. Competition over bioavailable iron is fierce both among bacteria in complex microbial communities and between bacterial pathogens and their eukaryotic hosts (2).Organisms have evolved various mechanisms of iron transport to obtain this essentia...

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Section: Discussionmentioning

confidence: 99%

Ferric Uptake Regulator Fur Control of Putative Iron Acquisition Systems in Clostridium difficile

Ellermeier

2015

J Bacteriol

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“…The chemical structure of petrobactin Ba was verified by Fourier transform ion cyclotron resonance (FTICR) mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectral analysis. To isolate petrobactin Mh , cultures of M. hydrocarbonoclasticus DSM 8798 precultured in Bacto marine broth (Difco) were grown in a synthetic seawater medium at 28°C for 7 days, as has been described previously (1,18). After fermentation broths were harvested by centrifugation, XAD-16 resin was added to each supernatant and the mixtures were agitated by shaking for 6 h at 150 rpm in the dark.…”

Section: Methodsmentioning

confidence: 99%

Biosynthetic Analysis of the Petrobactin Siderophore Pathway from Bacillusanthracis

Lee

Janes²,

Passalacqua³

et al. 2007

J Bacteriol

105

123

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The asbABCDEF gene cluster from Bacillus anthracis is responsible for biosynthesis of petrobactin, a catecholate siderophore that functions in both iron acquisition and virulence in a murine model of anthrax. We initiated studies to determine the biosynthetic details of petrobactin assembly based on mutational analysis of the asb operon, identification of accumulated intermediates, and addition of exogenous siderophores to asb mutant strains. As a starting point, in-frame deletions of each of the genes in the asb locus (asbABCDEF) were constructed. The individual mutations resulted in complete abrogation of petrobactin biosynthesis when strains were grown on iron-depleted medium. However, in vitro analysis showed that each asb mutant grew to a very limited extent as vegetative cells in iron-depleted medium. In contrast, none of the B. anthracis asb mutant strains were able to outgrow from spores under the same culture conditions. Provision of exogenous petrobactin was able to rescue the growth defect in each asb mutant strain. Taken together, these data provide compelling evidence that AsbA performs the penultimate step in the biosynthesis of petrobactin, involving condensation of 3,4-dihydroxybenzoyl spermidine with citrate to form 3,4-dihydroxybenzoyl spermidinyl citrate. As a final step, the data reveal that AsbB catalyzes condensation of a second molecule of 3,4-dihydroxybenzoyl spermidine with 3,4-dihydroxybenzoyl spermidinyl citrate to form the mature siderophore. This work sets the stage for detailed biochemical studies with this unique acyl carrier protein-dependent, nonribosomal peptide synthetase-independent biosynthetic system.

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“…16,17 As a result of the -hydroxy carboxylate group, the Fe(III)-complex of petrobactin is photoreactive in natural sunlight. 16,17 Recently, a Vibrio species isolated from the 4 These Gulf of Mexico after the BP oil spill was found to produce the suite of amphiphilic ochrobactins-OH siderophores, which are also photoreactive when complexed to Fe(III). 18 We report the structural characterization and iron(III) binding properties of lystabactin A, B 19 Bacterial growth was determined by measuring the optical density of the culture at 600 nm.…”

mentioning

confidence: 99%

Isolation, Structure Elucidation, and Iron-Binding Properties of Lystabactins, Siderophores Isolated from a Marine Pseudoalteromonas sp.

Zane

Butler

2013

J. Nat. Prod.

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The marine bacterium Pseudoalteromonas sp. S2B, isolated from the Gulf of Mexico after the Deepwater Horizon oil spill, was found to produce lystabactins A, B, and C (1−3), three new siderophores. The structures were elucidated through mass spectrometry, amino acid analysis, and NMR. The lystabactins are composed of serine (Ser), asparagine (Asn), two formylated/hydroxylated ornithines (FOHOrn), dihydroxy benzoic acid (Dhb), and a very unusual nonproteinogenic amino acid, 4,8-diamino-3-hydroxyoctanoic acid (LySta). The iron-binding properties of the compounds were investigated through a spectrophotometric competition.

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Petrobactin Sulfonate, a New Siderophore Produced by the Marine Bacterium Marinobacter hydrocarbonoclasticus

Cited by 68 publications

References 20 publications

Ferric Uptake Regulator Fur Control of Putative Iron Acquisition Systems in Clostridium difficile

Ferric Uptake Regulator Fur Control of Putative Iron Acquisition Systems in Clostridium difficile

Biosynthetic Analysis of the Petrobactin Siderophore Pathway from Bacillusanthracis

Isolation, Structure Elucidation, and Iron-Binding Properties of Lystabactins, Siderophores Isolated from a Marine Pseudoalteromonas sp.

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