Spirodionic acid, a novel metabolite from Streptomyces sp., part 1: structure elucidation and Diels-Alder-type biosynthesis |
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| Authors: | Textor Adriana Papastavrou Ina Siewert Jürgen Magull Jörg Kulik Andreas Fiedler Hans-Peter von Zezschwitz Paultheo Grond Stephanie |
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| Institution: | 1. Institut für Organische und Biomolekulare Chemie, Georg‐August‐Universit?t G?ttingen, Tammannstrasse 2, 37077 G?ttingen, Germany, Fax: (+49)?551‐391‐2593;2. Institut für Anorganische Chemie, Georg‐August‐Universit?t G?ttingen, Tammannstrasse 4, 37077 G?ttingen, Germany;3. Mikrobiologisches Institut, Eberhard Karls Universit?t Tübingen, Auf der Morgenstelle 28, 72076 Tübingen, Germany |
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| Abstract: | Spirodionic acid (1), a novel microbial metabolite with a spiro4.5]decene skeleton, the 6-ethyl-2H-pyrone 5, dihydrosarkomycin (6), and other metabolites were isolated from the strain Streptomyces sp. Tü 6077. Structural elucidation was accomplished by NMR spectroscopic and mass-spectrometric studies, and the biosyntheses of compounds 1, 5, and 6 were investigated by feeding experiments with (13)C-labeled precursors. All results indicate a biogenetic sequence with metabolite 5 and sarkomycin (7) as precursors in the formation of spirocyclus 1 through an intermolecular Diels-Alder-type reaction. |
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| Keywords: | biosynthesis natural products spiro compounds streptomyces structure elucidation |
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