Isolation, Structure Elucidation, and Biological Activity of Maltepolides: Remarkable Macrolides from Myxobacteria

Authors

  • Dr. Herbert Irschik,

    1. Helmholtz Centre for Infection Research (HZI), Inhoffenstrasse 7, 38124 Braunschweig (Germany)
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  • Dr. Peter Washausen,

    1. Helmholtz Centre for Infection Research (HZI), Inhoffenstrasse 7, 38124 Braunschweig (Germany)
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  • Dr. Florenz Sasse,

    1. Helmholtz Centre for Infection Research (HZI), Inhoffenstrasse 7, 38124 Braunschweig (Germany)
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  • Dr. Jörg Fohrer,

    1. Department of NMR Spectroscopy, Institute of Organic Chemistry, University of Hannover, Schneiderberg 1B, 30167 Hannover (Germany)
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  • Dr. Volker Huch,

    1. Institute of Inorganic Chemistry, Saarland University, Campus, Gebäude B 2.2 66123 Saarbrücken (Germany)
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  • Prof. Dr. Rolf Müller,

    1. Helmholtz Centre for Infection Research (HZI), Inhoffenstrasse 7, 38124 Braunschweig (Germany)
    2. Department of Microbial Natural Products, Helmholtz-Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI) and Pharmaceutical Biotechnology, Saarland University, Campus C2 3, 66123 Saarbrücken (Germany)
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  • Dr. Evgeny V. Prusov

    Corresponding author
    1. Helmholtz Centre for Infection Research (HZI), Inhoffenstrasse 7, 38124 Braunschweig (Germany)
    • Helmholtz Centre for Infection Research (HZI), Inhoffenstrasse 7, 38124 Braunschweig (Germany)
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  • We acknowledge the contributions of A. Meier and T. Hirsch to the isolation of maltepolides and support from the HZI Biotechnology platform during the fermentations. We are also indebted to Prof. Dr. G. Höfle for many stimulating discussions and to Dr. F. Surup and C. Brünjes for some valuable suggestions. We thank Dr. R. Jansen and Dipl.-Ing. H. Steinmetz for assistance in acquiring LC/MS data and C. Kakoschke for some special NMR measurements.

Abstract

original image

Epoxide “swing”: A family of polyketide macrolactones originating from maltepolide E was discovered in Sorangium cellulosum So ce1485. Their structure was established by NMR experiments, molecular modeling, and X-ray crystallography. Maltepolides induce rather rare morphological changes in the dividing transformed cell lines (see picture in the background).

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