Stoffwechselprodukte von Mikroorganismen 49. Mitteilung. Die Ferrioxamine A1, A2 und D2

Keller‐Schierlein, W.; Mertens, Peter; Prelog, V.; Walser, A.

doi:10.1002/hlca.19650480407

Cited by 36 publications

(8 citation statements)

References 23 publications

(9 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Hydroxamate siderophores-DFOB is a tris-hydroxamate terrestrial bacterial siderophore produced by gram-positive actinomycetes and by several gram-negative species (Keller-Schierlein et al 1965;Mucha et al 1999). Recently, desferrioxamine G, a siderophore very similar in structure to DFOB, was shown to be produced by a coastal marine Vibrio species (Martinez et al 2001).…”

Section: Resultsmentioning

confidence: 99%

Photochemical reactivity of siderophores produced by marine heterotrophic bacteria and cyanobacteria based on characteristic Fe(III) binding groups

Barbeau

Rue

Trick

et al. 2003

Limnology & Oceanography

229

190

View full text Add to dashboard Cite

Siderophores, high-affinity Fe(III) ligands produced by microorganisms to facilitate iron acquisition, might contribute significantly to dissolved Fe(III) complexation in ocean surface waters. In previous work, we demonstrated the photoreactivity of the ferric ion complexes of several ␣-hydroxy carboxylic acid-containing siderophores produced by heterotrophic marine bacteria. Here, we expand on our earlier studies and detail the photoreactivity of additional siderophores produced by both heterotrophic marine bacteria and marine cyanobacteria, making comparisons to synthetic and terrestrial siderophores that lack the ␣-hydroxy carboxylate group. Our results suggest that, in addition to secondary photochemical reaction pathways involving reactive oxygen species, direct photolysis of Fe(III)-siderophore complexes might be a significant source of Fe(II) and reactive Fe(III) in ocean surface waters. Our findings further indicate that the photoreactivity of siderophores is primarily determined by the chemical structure of the Fe(III) binding groups that they possess-hydroxamate, catecholate, or ␣-hydroxy carboxylate moieties. Hydroxamate groups are photochemically resistant regardless of Fe(III) complexation. Catecholates, in contrast, are susceptible to photooxidation in the uncomplexed form but stabilized against photooxidation when ferrated. ␣-Hydroxy carboxylate groups are stable as the uncomplexed acid, but when coordinated to Fe(III), these moieties undergo light-induced ligand oxidation and reduction of Fe(III) to Fe(II). These photochemical properties appear to determine the reactivity and fate of Fe(III)-binding siderophores in ocean surface waters, which in turn might significantly influence the biogeochemical cycling of iron.In the oceans, the speciation of dissolved iron, an important limiting micronutrient for marine phytoplankton, has been shown to be dominated by complexation with strong organic ligands (Gledhill and Van den Berg 1994;Rue and Bruland 1995;Powell and Donat 2001). Factors that control

show abstract

Section: Resultsmentioning

confidence: 99%

Photochemical reactivity of siderophores produced by marine heterotrophic bacteria and cyanobacteria based on characteristic Fe(III) binding groups

Barbeau

Rue

Trick

et al. 2003

Limnology & Oceanography

229

190

View full text Add to dashboard Cite

show abstract

“…Six organic Fe complexes were chosen for this study: two synthetic metal chelators, ethylenediaminetetraacetic acid (EDTA) and diethyltriaminepentaacetic acid (DTPA), and four natural, strong organic Fe ligands: desferrioxamine B (DFB), rhodotorulic acid, (–) ‐gallocatechin, and phytic acid. Desferrioxamine B is a linear hexadentate trihydroxamic acid siderophore produced by species of the terrestrial bacteria Streptomyces and Nocardia [ Keller‐Schierlein et al , 1965; Mueller and Raymond , 1984]. Rhodotorulic acid is a tetradentate linear dihydroxymate bacterial siderophore isolated from Rhodotorula pilimanae [ Atkin and Neilands , 1968].…”

Section: Methodsmentioning

confidence: 99%

Acquisition of iron bound to strong organic complexes, with different Fe binding groups and photochemical reactivities, by plankton communities in Fe‐limited subantarctic waters

Maldonado

Strzepek

Sander

et al. 2005

Global Biogeochemical Cycles

142

177

View full text Add to dashboard Cite

[1] Though it is clear that plankton in oceanic regions access iron bound to strong organic ligands, the mechanism mediating the release of iron from these complexes remains unresolved. In this study, we aim to elucidate the mechanisms of organic iron acquisition by plankton in subantarctic waters. In particular, we investigated the importance of photochemistry in mediating the reductive dissociation of iron from organic complexes, using naturally occurring ligands, and model iron complexes, with different iron-binding groups and photoreactivities. Our results demonstrate that iron within the model ligands is available for uptake and growth by indigenous plankton, but that photolability of these complexes does not determine iron bioavailability. In contrast, light significantly enhances iron acquisition from the in situ ligands, suggesting that the in situ iron ligands are photolabile, and that photochemistry in surface waters may play a significant role in iron uptake from the dissolved organic iron pool by oceanic plankton.

show abstract

“…1). Up to five different compounds from the set comprising DFOA 1 , DFOA 2 , DFOD 1 , DFOD 2 , DFOB, DFOE, DFOG, or DFOH, have been reported as biosynthetic products from different Streptomyces species, [57][58][59][60][61][62][63][64][65] but to the best of our knowledge, this is the highest number of siderophores from the desferrioxamine class produced by a single actinomycete species. The ability to detect these low abundance species was due to the resolution of the siderophore metabolome afforded by Ni(II)based IMAC.…”

Section: Characterisation Of Siderophoresmentioning

confidence: 99%

The variable hydroxamic acid siderophore metabolome of the marine actinomycete Salinispora tropica CNB-440

Ejje¹,

Soe²,

Gu³

et al. 2013

Metallomics

View full text Add to dashboard Cite

The recently sequenced genome of the marine actinomycete Salinispora tropica CNB-440 revealed a high frequency of gene clusters which code for the biosynthesis of known and novel secondary metabolites. Of these metabolites, bioinformatics analysis predicted that S. tropica CNB-440 could potentially biosynthesize, as high affinity Fe(iii) ligands, siderophores from the hydroxamic acid desferrioxamine class (sid1 gene cluster) and the phenolate-thia(oxa)zoli(di)ne class (sid2 and sid4 gene clusters). In this work, we have used Ni(ii)-based immobilized metal ion affinity chromatography (IMAC) to pre-fractionate the hydroxamic acid siderophore metabolome of S. tropica CNB-440 from the secondary metabolome, to reveal low abundance siderophores. LC-MS measurements and electronic absorption spectra from purified extracts incubated with exogenous Fe(iii) revealed eight siderophores from the desferrioxamine class (DFOA2, DFOA1a, DFOA1b, DFOB, DFON, DFOD2, DFOE, DFOD1), which included two constitutional isomers (DFOA1a, DFOA1b), and one new siderophore (DFON), the latter which would require assembly from a combination of 1,5-diaminopentane and 1,6-diaminohexane as diamine substrates. Three additional species (m/zobs 496.14, 792.34 and 804.34) with electronic absorption spectra characteristic of complexes formed between Fe(iii) and hydroxamic acid-type siderophores were evident under some conditions. The signal at m/zobs 792.34 eluted in the hydrophobic region of the reverse-phase LC and correlated with a DFOD1 analogue with a C-terminal branched chain fatty acid ([M + K(+)](+)m/zcalc 792.35), which has been previously identified from marine sediment dwelling Micrococcus luteus KLE1011. The S. tropica CNB-440 hydroxamic acid siderophore metabolome was modulated by culture conditions (pH 7, 22 °C; pH 7, 28 °C; pH 9, 28 °C) designed to simulate the variable marine environment. An increase in temperature at constant pH value showed increased levels of DFOA2 and DFOA1, and decreased levels of DFOB and DFOE. An increase in pH value at constant temperature showed decreased levels of DFOA2 and DFOA1, and increased levels of DFOB, DFON and DFOE. These results indicate that the marine adaptation of S. tropica CNB-440 could involve its ability to select a suite of siderophores from a large number of candidates, which are optimized for the iron microenvironment.

show abstract

Stoffwechselprodukte von Mikroorganismen 49. Mitteilung. Die Ferrioxamine A₁, A₂ und D₂

Cited by 36 publications

References 23 publications

Photochemical reactivity of siderophores produced by marine heterotrophic bacteria and cyanobacteria based on characteristic Fe(III) binding groups

Photochemical reactivity of siderophores produced by marine heterotrophic bacteria and cyanobacteria based on characteristic Fe(III) binding groups

Acquisition of iron bound to strong organic complexes, with different Fe binding groups and photochemical reactivities, by plankton communities in Fe‐limited subantarctic waters

The variable hydroxamic acid siderophore metabolome of the marine actinomycete Salinispora tropica CNB-440

Contact Info

Product

Resources

About