Spirodionic acid, a novel metabolite from Streptomyces sp., part 1: structure elucidation and Diels-Alder-type biosynthesis.
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.
Textor
Adriana
A
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany.
Papastavrou
Ina
I
Siewert
Jürgen
J
Magull
Jörg
J
Kulik
Andreas
A
Fiedler
Hans-Peter
HP
von Zezschwitz
Paultheo
P
Grond
Stephanie
S
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*
D003470:Culture Media; D013141:Spiro Compounds; C523960:spirodionic acid; D005990:Glycerol