2021
DOI: 10.3762/bjoc.17.156
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Isolation and characterization of new phenolic siderophores with antimicrobial properties from Pseudomonas sp. UIAU-6B

Abstract: Five new phenolic siderophores 1–5 were isolated from the organic extract of a culture broth in a modified SGG medium of Pseudomonas sp. UIAU-6B, obtained from sediments collected from the Oyun river in North Central Nigeria. The structure of the new compounds, pseudomonin A–C (1–3) and pseudomobactin A and B (4 and 5) isolated alongside two known compounds, pseudomonine (6) and salicylic acid (7), were elucidated based on high-resolution mass spectrometry, 1D and 2D NMR analyses. The absolute configuration of… Show more

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Cited by 3 publications
(6 citation statements)
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“…Measurements of 2 were not possible due to the low quantity of isolated material, but it stands to reason that its configuration is identical to 5 under the assumption of a shared biosynthetic origin. Compound 6 shows an optical rotation of = −10.6, which is consistent with the published value of pseudomonin A ( = −9.5) [ 12 ]. This natural product is structurally closely related to 6 , featuring a terminal amide instead of a carboxylic acid function.…”
Section: Resultssupporting
confidence: 87%
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“…Measurements of 2 were not possible due to the low quantity of isolated material, but it stands to reason that its configuration is identical to 5 under the assumption of a shared biosynthetic origin. Compound 6 shows an optical rotation of = −10.6, which is consistent with the published value of pseudomonin A ( = −9.5) [ 12 ]. This natural product is structurally closely related to 6 , featuring a terminal amide instead of a carboxylic acid function.…”
Section: Resultssupporting
confidence: 87%
“…Compound 6 represents a possible shunt product of amamistatin biosynthesis. A similar molecule and its putative biosynthetic pathway were recently described by Jaspars et al [ 12 ]. In accordance with this proposal, salicylic acid and ʟ-threonine would form a salimethyloxazolinyl-thioester intermediate, which then undergoes a C–N bond opening resulting in an ester formation.…”
Section: Resultsmentioning
confidence: 70%
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“…In the isolated Pseudomonas strains, this points to a potential role of this siderophore in the inhibition of the three lettuce bacterial pathogens. Pseudomonine and pseudomonine-like compounds are siderophores identified in various Pseudomonas strains of biocontrol interest ( Mercado-Blanco et al, 2001 ; Loper et al, 2012 ; Biessy et al, 2019 ; Oluwabusola et al, 2021 ). They share structural similarities with pyochelin ( Gross and Loper, 2009 ).…”
Section: Discussionmentioning
confidence: 99%
“…They share structural similarities with pyochelin ( Gross and Loper, 2009 ). Some of these compounds have been shown to inhibit the human bacterial pathogen Mycobacterium tuberculosis in vitro ( Oluwabusola et al, 2021 ). Another family of BGCs found in the genome of the 35 strains under study pertains to NRPS and PKS.…”
Section: Discussionmentioning
confidence: 99%