New cineromycins and musacins obtained by metabolite pattern analysis of Streptomyces griseoviridis (FH-S 1832). II. Structure elucidation.
A detailed analysis of the secondary metabolite pattern produced by Streptomyces griseoviridis (strain FH-S 1832) using a chemical screening method resulted in the detection, isolation and structure elucidation of new 14-membered lactones of the cineromycin B-type [dehydrocineromycin B (5), oxycineromycin B (7), and 2,3-dihydrocineromycin B (8)], as well as new gamma-lactones related to nigrosporalactone and 4,5-dihydroxy-octa-2,6-dienoic acid esters named musacins A to F (10, 13 approximately 15, 17, 18 and 21). The constitution of these metabolites were deduced from spectroscopic data as well as chemical transformations. The configuration of musacin D (10) was determined by derivatization with chiral acids (Helmchen's method).
Schneider
A
A
Institut für Organische Chemie, Universität Göttingen, Germany.
Späth
J
J
Breiding-Mack
S
S
Zeeck
A
A
Grabley
S
S
Thiericke
R
R
D005285:Fermentation; D007783:Lactones / Q000737:chemistry* / Q000302:isolation & purification*; D015394:Molecular Structure; D013302:Streptomyces / Q000378:metabolism*; D013329:Structure-Activity Relationship
D007783:Lactones