Novel siderophore, JBIR-16, isolated from Nocardia tenerifensis NBRC 101015

Mukai, Akira; Komaki, Hisayuki; Takagi, Motoki; Shin‐ya, Kazuo

doi:10.1038/ja.2009.84

Cited by 23 publications

(11 citation statements)

References 17 publications

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“…In the original papers describing the structures of heterobactins A ( 1 ) and B ( 2 ) 11 and Nocardia heterobactin ( 3 ), 12 the authors offer some preliminary evidence regarding the stoichiometry of the siderophore/iron complexes. The evidence, largely mass spectral data, is in keeping with the idea that heterobactin A and B and Nocardia heterobactin all form 1:1 ligand/metal complexes.…”

Section: Resultsmentioning

confidence: 99%

“…12 R. erythropolis has drawn considerable attention recently because of the ability of particular strains to metabolize oil, making these organisms attractive candidates as tools for bioremediation. 13 This potential application adds value to the current work.…”

Section: Introductionmentioning

confidence: 99%

“…The donor ligands consist of the terminal 2,3-dihydroxybenzoyl hydroxyls, the central oxazoline nitrogen, and the internal aromatic hydroxyl. Heterobactin A ( 1 ) and B ( 2 ), from Rhodococcus , 11 and the heterobactin analogue ( 3) from Nocardia 12 also present with terminal bidentate fragments, although unsymmetrical: on one end, a 2,3-dihydroxybenzoyl, on the other, a hydroxamate derived from cyclized N 5 -OH-L-ornithine. The central donor in heterobactin A ( 1 ), a 5-hydroxy-4-carboxyl-benzoxazole may employ the aromatic hydroxyl and the amide function, as has been previously observed.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of heterobactins A and B and Nocardia heterobactin

2011

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The synthesis of the Rhodococcus erythropolis siderophores heterobactins A and B, and the structurally related Nocardia heterobactin, is described. Two approaches for the assembly of these asymmetric ligand donor chelators are explored. In the first approach, a scheme predicated on the biosynthesis of the Paracoccus denitrificans siderophore, parabactin, is employed. In this approach, the central donor synthon is added last. In the second scheme, the central donor and the terminal 2,3-dihydroxybenzoyl fragment are first fixed to the ligand’s D-ornithine backbone. This is followed by condensation with the cyclic ornithine hydroxamate glycine segment. The schemes offer a flexible approach to other heterobactins. Job’s plots suggest that heterobactin A and Nocardia heterobactin form 1:1 ligand/metal complexes, while heterobactin B forms a 3:2 ligand/metal complex.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of heterobactins A and B and Nocardia heterobactin

2011

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“…Heterobactin siderophores are mixed catechol-hydroxamate siderophores and were first discovered in Rhodococcus erythropolis IGTS8, a member of the actinomycetes (Carrano et al 2001). The production of a heterobactin-like siderophore by Nocardia tenerifensis NBRC 101015, also an actinomycete, was later discovered (Mukai et al 2009). Isolate 2350 was identified as a Streptomyces species on the basis of its morphological characteristics and 16S rRNA sequencing results and this is the first report describing putative heterobactin production by Streptomyces species.…”

Section: Discussionmentioning

confidence: 97%

“…Streptomyces are actinomycetes and most commonly produce some type of trihydroxamate siderophore known as desferrioxamine (Imbert et al 1995;Meiwes et al 1990;Yamanaka et al 2005) but reports have described isolates capable of producing enterobactin (Fiedler et al 2001) the characteristic siderophore of Enterobacteriaceae, that was not excreted into the external environment but remained in the bacterial biomass. Others have described the Streptomyces siderophores coelichelin (Challis and Ravel 2000;Lautru et al 2005) and griseobactin (Patzer and Braun 2010), while the novel heterobactin siderophores have been found in Rhodococcus (Carrano et al 2001) and Nocardia (Mukai et al 2009). …”

Section: Introductionmentioning

confidence: 96%

Siderophore production by actinomycetes isolates from two soil sites in Western Australia

et al. 2011

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The actinomycetes are metabolically flexible soil micro-organisms capable of producing a range of compounds of interest, including siderophores. Siderophore production by actinomycetes sampled from two distinct and separate geographical sites in Western Australia were investigated and found to be generally similar in the total percentage of siderophore producers found. The only notable difference was the proportion of isolates producing catechol siderophores with only 3% found in site 1 (from the north-west of Western Australia and reportedly containing 40% magnetite) and 17% in site 2 (a commercial stone fruit orchard in the hills east of Perth with a soil base ranging from sandy loam to laterite). Further detailed characterization of isolates of interest identified a Streptomyces that produced extracellularly excreted enterobactin, the characteristic Enterobacteriaceae siderophore, and also revealed some of the conditions required for enterobactin production. Carriage of the entF gene, which codes for the synthetase responsible for the final assembly of the tri-cyclic structure of enterobactin, was confirmed by PCR in this isolate. Another separate Streptomyces produced a compound that matched the UV/VIS spectra of heterobactin, a siderophore previously only described in Rhodococcus and Nocardia.

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Unprecedented 17‐Residue Peptaibiotics Produced by Marine‐Derived Trichoderma atroviride

Carroux¹,

Bohemen²,

Roullier³

et al. 2013

Chemistry & Biodiversity

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In the course of investigations on marine-derived toxigenic fungi, five strains of Trichoderma atroviride were studied for their production of peptaibiotics. While these five strains were found to produce classical 19-residue peptaibols, three of them exhibited unusual peptidic sodium-adduct [M + 2 Na](2+) ion peaks at m/z between 824 and 854. The sequencing of these peptides led to two series of unprecedented 17-residue peptaibiotics based on the model Ac-XXX-Ala-Ala-XXX-XXX-Gln-Aib-Aib-Aib-Ala/Ser-Lxx-Aib-Pro-XXX-Aib-Lxx-[C(129) ]. The C-terminus of these new peptides was common to all of them, and its elemental formula C5 H9 N2 O2 was established by HR-MS. It could correspond to the cyclized form of N(δ) -hydroxyornithine which has already been observed at the C-terminus of various peptidic siderophores. The comparison of the sequences of 17- and 19-residue peptides showed similarities for positions 1-16. This observation seems to indicate a common biosynthesis pathway. Both new 17-residue peptaibiotics and 19-residue peptaibols exhibited weak in vitro cytotoxicities against KB cells.

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Novel siderophore, JBIR-16, isolated from Nocardia tenerifensis NBRC 101015

Cited by 23 publications

References 17 publications

Synthesis of heterobactins A and B and Nocardia heterobactin

Synthesis of heterobactins A and B and Nocardia heterobactin

Siderophore production by actinomycetes isolates from two soil sites in Western Australia

Unprecedented 17‐Residue Peptaibiotics Produced by Marine‐Derived Trichoderma atroviride

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