Leukaemomycin-geblockte Mutanten des Streptomyces griseus und ihre Pigmente III. 11-Desoxydaunomycinonderivate aus der Mutante ZIMET 43699/G44

✍ Scribed by Christina Wagner; K. Eckardt; D. Tresselt; W. Ihn; G. Schumann; W. F. Fleck

• Publisher: John Wiley and Sons
• Year: 1985
• Tongue: English
• Weight: 486 KB
• Volume: 25
• Category: Article
• ISSN: 0233-111X
• DOI: 10.1002/jobm.3620251021

✦ Synopsis

The isolation and identification of several anthracyclinones (designated as G44-K4/5, G44-G1, G44-G2) and anthracyclines (G44-A, B, C, D, E, F , G) produced by the mutant strain IMET J A 3933/G44 of the daunomycin-producing Streptomyces griseus strain IMET J A 3933 are described. G44-K4/5 was found to be identical with j7,1l-dideoxy-13-dihydrodaunomycinone previously isolated from a mutant strain of Xtreptomyces coeruleorubidus. Compound G44-G1 was identified as 11 -deoxydaunomycinone, the aglycone of the antibiotic 11 -deoxydaunomycin. G44-G2 was found to be a stereoisomer of G44-G1. The NMR and CD spectral data suggest strongly that the compound is 7-epi-11-deoxydaunomycinone. Of the 7 isolated G44-glycosides only the major component G44-B could be identified. Comparison with an authentic sample revealed that this compound is 11-deoxydaunomycin which had previously been isolated from cultures of Streptomyces peucetius var. aureus and Micromonospora peucetica. As reported for S. coeruleorubidus, S. peucetius var. aureus, and Micromonospora peucetica the 11 -deoxydaunomycinone derivatives described in this paper were isolated from the fermentation broth of a mutant of a daunomycinproducing wild type strain. This suggests that in general the accumulation of 11-deoxydaunomycinone derivatives may be the result of a block of C,,-hydroxylation in the normal biosynthetic pathway of daunomycin and its analogues.