Legonoxamines A-B,two new hydroxamate siderophores from the soil bacterium, Streptomyces sp. MA37 |
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Authors: | Fleurdeliz Maglangit Ming Him Tong Marcel Jaspars Kwaku Kyeremeh Hai Deng |
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Institution: | 1. Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, UK;2. College of Science, University of the Philippines Cebu, Lahug, Cebu City 6000, Philippines;3. Department of Chemistry, University of Ghana, P.O. Box LG56, Legon-Accra, Ghana |
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Abstract: | Two new siderophores belonging to the hydroxamate class, Legonoxamine A (1) and B (2) have been isolated from the soil bacterium, Streptomyces sp. MA37, together with one known compound, desferrioxamine B (3). Their structures were elucidated based on spectroscopic methods including 1D, 2D NMR, MS, as well as by comparison with the relevant literatures. To our knowledge, this is the first report describing a siderophore containing the N-hydroxyl phenylacetyl cadaverine (HPAC) moiety in the structure. Based on bioinformatics analysis and previous knowledge of the biosynthesis of the hydroxamate-type siderophore, the biosynthetic gene cluster (lgo) responsible for the production of 1–3 was identified in the annotated genome of the producing strain. The supplementation of phenylacetate and benzoate analogues with meta substitution into the cultures of Streptomyces sp. MA37 resulted in the production of new legonoxamine A derivatives as observed in LC-HR-ESIMS, suggesting that the legonoxamine biosynthetic pathway has a good degree of natural flexibility of accepting unnatural precursors with different functional groups. |
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Keywords: | Siderophores Hydroxamates Legonoxamine Precursor-directed biosynthesis |
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