title: Spirodionic acid, a novel metabolite from Streptomyces sp., part 1: structure elucidation and Diels-Alder-type biosynthesis.
abstract: Spirodionic acid (1), a novel microbial metabolite with a spiro[4.5]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.
authors.affiliation: Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany.
authors.forename: Adriana
authors.initials: A
authors.lastname: Textor
authors.forename: Ina
authors.initials: I
authors.lastname: Papastavrou
authors.forename: Jürgen
authors.initials: J
authors.lastname: Siewert
authors.forename: Jörg
authors.initials: J
authors.lastname: Magull
authors.forename: Andreas
authors.initials: A
authors.lastname: Kulik
authors.forename: Hans-Peter
authors.initials: HP
authors.lastname: Fiedler
authors.forename: Paultheo
authors.initials: P
authors.lastname: von Zezschwitz
authors.forename: Stephanie
authors.initials: S
authors.lastname: Grond
mesh_terms: D018360:Crystallography, X-Ray; D003470:Culture Media; D005285:Fermentation; D005990:Glycerol / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D013058:Mass Spectrometry; D008958:Models, Molecular; D025282:Mycelium / Q000737:chemistry / Q000378:metabolism; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013141:Spiro Compounds / Q000737:chemistry*; D013302:Streptomyces / Q000737:chemistry*
chemical_list: D003470:Culture Media; D013141:Spiro Compounds; C523960:spirodionic acid; D005990:Glycerol