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

Autor: Bill MK; Branch for Bioresources, Fraunhofer Institute for Molecular Biology and Applied Ecology (IME), Ohlebergsweg 12, 35392, Giessen, Germany., Kleiner Y; Branch for Bioresources, Fraunhofer Institute for Molecular Biology and Applied Ecology (IME), Ohlebergsweg 12, 35392, Giessen, Germany., Flügel JL; Branch for Bioresources, Fraunhofer Institute for Molecular Biology and Applied Ecology (IME), Ohlebergsweg 12, 35392, Giessen, Germany.; Institute of Organic Chemistry, Justus-Liebig University Giessen, Heinrich-Buff-Ring 17, 35392, Giessen, Germany., Kurz M; Sanofi-Aventis Deutschland GmbH, R&D Integrated Drug Discovery, Industriepark Höchst, 65926, Frankfurt am Main, Germany., Spohn M; Branch for Bioresources, Fraunhofer Institute for Molecular Biology and Applied Ecology (IME), Ohlebergsweg 12, 35392, Giessen, Germany., Marner M; Branch for Bioresources, Fraunhofer Institute for Molecular Biology and Applied Ecology (IME), Ohlebergsweg 12, 35392, Giessen, Germany., Mihajlovic S; Branch for Bioresources, Fraunhofer Institute for Molecular Biology and Applied Ecology (IME), Ohlebergsweg 12, 35392, Giessen, Germany., Vilcinskas A; Branch for Bioresources, Fraunhofer Institute for Molecular Biology and Applied Ecology (IME), Ohlebergsweg 12, 35392, Giessen, Germany.; Institute for Insect Biotechnology, Justus-Liebig University Giessen, Heinrich-Buff-Ring 26-32, 35392, Giessen, Germany., Schäberle TF; Branch for Bioresources, Fraunhofer Institute for Molecular Biology and Applied Ecology (IME), Ohlebergsweg 12, 35392, Giessen, Germany.; Institute for Insect Biotechnology, Justus-Liebig University Giessen, Heinrich-Buff-Ring 26-32, 35392, Giessen, Germany., Hammann PE; Sanofi-Aventis Deutschland GmbH, R&D Integrated Drug Discovery, Industriepark Höchst, 65926, Frankfurt am Main, Germany.; Evotec International GmbH, Marie-Curie-Straße 7, 37079, Göttingen, Germany., Patras MA; Branch for Bioresources, Fraunhofer Institute for Molecular Biology and Applied Ecology (IME), Ohlebergsweg 12, 35392, Giessen, Germany. Maria.Patras@ime.fraunhofer.de., Schuler SMM; Evotec International GmbH, Marie-Curie-Straße 7, 37079, Göttingen, Germany. Soeren.Schuler@evotec.com.
Jazyk: angličtina
Zdroj: The Journal of antibiotics [J Antibiot (Tokyo)] 2022 Oct; Vol. 75 (10), pp. 576-582. Date of Electronic Publication: 2022 Sep 02.
DOI: 10.1038/s41429-022-00557-z
Abstrakt: 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 µg ml -1 against Moraxella catarrhalis. Therefore, this study enlarges the family of madurastatin siderophores.
(© 2022. The Author(s), under exclusive licence to the Japan Antibiotics Research Association.)
Databáze: MEDLINE
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