Isolation, characterization, and bioactivity profiling of oxazoline containing madurastatin siderophores from Actinomadura sp

Nine new hydroxyphenyloxazolines, madurastatin B4, C2, D3 and D4, E1 and E2, F1 as well as G1 and G2 ( 8 – 16 ), along with two new enantiomers of madurastatin D1 ( ent - 6 ) and D2 ( ent - 7 ) and two known congeners, madurastatin B1 ( 2 ) and C1 ( 5 ), were isolated from the liquid culture of Acti...

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Bibliographic Details
Published in:Journal of antibiotics 2022-10, Vol.75 (10), p.576-582
Main Authors: Bill, Mona-K., Kleiner, Yolanda, Flügel, Jana L., Kurz, Michael, Spohn, Marius, Marner, Michael, Mihajlovic, Sanja, Vilcinskas, Andreas, Schäberle, Till F., Hammann, Peter E., Patras, Maria A., Schuler, Sören M. M.
Format: Article
Language:English
Subjects:
639/638/11
639/638/403/936
692/699/255/1318
Absolute configuration
Actinomadura
Anti-Bacterial Agents - chemistry
Antibacterial activity
Antibiotics
Bacteriology
Bicarbonates
Biological activity
Biomedical and Life Sciences
Bioorganic Chemistry
Brief Communication
Congeners
E coli
Enantiomers
Escherichia coli
Life Sciences
Liquid culture
Medicinal Chemistry
Microbial Sensitivity Tests
Microbiology
Microorganisms
Molecular Structure
Natural products
NMR
Nuclear magnetic resonance
Organic Chemistry
Siderophores
Tandem Mass Spectrometry
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Summary:Nine new hydroxyphenyloxazolines, madurastatin B4, C2, D3 and D4, E1 and E2, F1 as well as G1 and G2 ( 8 – 16 ), along with two new enantiomers of madurastatin D1 ( ent - 6 ) and D2 ( ent - 7 ) and two known congeners, madurastatin B1 ( 2 ) and C1 ( 5 ), were isolated from the liquid culture of Actinomadura sp. ST100801 based on the initial activity against Escherichia coli screened in bicarbonate-supplemented Mueller Hinton II medium and identification via molecular networking. Structure elucidation was achieved by comprehensive 1D and 2D NMR as well as MS/MS fragmentation analyses. Their absolute configuration was determined by Marfey’s analysis. Complemented with functionalized hydroxyphenyloxazolines ( 2 , 4 ,  17 – 18 ) obtained by total synthesis, the isolated compounds were evaluated for antibacterial activities revealing MICs down to 4  µ g ml −1 against Moraxella catarrhalis . Therefore, this study enlarges the family of madurastatin siderophores.
ISSN:0021-8820
1881-1469
DOI:10.1038/s41429-022-00557-z