Divergolides A–D from a Mangrove Endophyte Reveal an Unparalleled Plasticity in ansa-Macrolide Biosynthesis

Authors

  • Dr. Ling Ding,

    1. Leibniz Institute for Natural Product Research and Infection Biology, HKI, Dept. of Biomolecular Chemistry and Bio Pilot Plant, Beutenbergstrasse 11a, 07745 Jena (Germany), Fax: (+49) 3641-532-0804
    Search for more papers by this author
  • Dr. Armin Maier,

    1. Oncotest GmbH, Freiburg (Germany)
    Search for more papers by this author
  • Prof. Dr. Heinz-Herbert Fiebig,

    1. Oncotest GmbH, Freiburg (Germany)
    Search for more papers by this author
  • Dr. Helmar Görls,

    1. Institute for Inorganic and Analytical Chemistry, Friedrich Schiller University, Jena (Germany)
    Search for more papers by this author
  • Prof. Dr. Wen-Han Lin,

    1. State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing (China)
    Search for more papers by this author
  • Dr. Gundela Peschel,

    1. Leibniz Institute for Natural Product Research and Infection Biology, HKI, Dept. of Biomolecular Chemistry and Bio Pilot Plant, Beutenbergstrasse 11a, 07745 Jena (Germany), Fax: (+49) 3641-532-0804
    Search for more papers by this author
  • Prof. Dr. Christian Hertweck

    Corresponding author
    1. Leibniz Institute for Natural Product Research and Infection Biology, HKI, Dept. of Biomolecular Chemistry and Bio Pilot Plant, Beutenbergstrasse 11a, 07745 Jena (Germany), Fax: (+49) 3641-532-0804
    2. Chair for Natural Product Chemistry, Friedrich Schiller University, Jena (Germany)
    • Leibniz Institute for Natural Product Research and Infection Biology, HKI, Dept. of Biomolecular Chemistry and Bio Pilot Plant, Beutenbergstrasse 11a, 07745 Jena (Germany), Fax: (+49) 3641-532-0804
    Search for more papers by this author

  • We thank A. Perner, H. Heinecke, and F. Rhein for MS and NMR measurements, U. Valentin for SPE, C. Heiden and M. Steinacker for fermentation and downstream processing, and C. Weigel for performing biological assays. This research was financially supported by the Federal Ministry of Science and Technology (BMBF, Germany).

Abstract

original image

In-built diversification: Four ansa macrolides, divergolides A–D (14), with intriguing structures were isolated from a bacterial endophyte of the mangrove tree Bruguiera gymnorrhiza. These compounds are generated by a common biogenesis from a linear precursor that undergoes various reactions to give the multicyclic structures. This remarkable plasticity results in metabolites with different antibacterial and cytotoxic properties.

Ancillary