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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 JA 3933/G44 of the daunomycin-producing Streptomyces griseus strain IMET JA 3933 are described. G44-K4/5 was found to be identical with 7,11-dideoxy-13-dihydrodaunomycinone previously isolated from a mutant strain of Streptomyces 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 daunomycin-producing wild type strain. This suggest that in general the accumulation of 11-deoxydaunomycinone derivatives may be the result of a block of C11-hydroxylation in the normal biosynthetic pathway of daunomycin and its analogues.
C Wagner, and
K Eckardt, and
D Tresselt, and
W Ihn, and
G Schumann, and
W F Fleck
January 1984,
Zeitschrift fur allgemeine Mikrobiologie,
C Wagner, and
K Eckardt, and
D Tresselt, and
W Ihn, and
G Schumann, and
W F Fleck
January 1981,
Zeitschrift fur allgemeine Mikrobiologie,
C Wagner, and
K Eckardt, and
D Tresselt, and
W Ihn, and
G Schumann, and
W F Fleck
January 1983,
Zeitschrift fur allgemeine Mikrobiologie,
C Wagner, and
K Eckardt, and
D Tresselt, and
W Ihn, and
G Schumann, and
W F Fleck
March 1982,
The Journal of antibiotics,
C Wagner, and
K Eckardt, and
D Tresselt, and
W Ihn, and
G Schumann, and
W F Fleck
May 1984,
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C Wagner, and
K Eckardt, and
D Tresselt, and
W Ihn, and
G Schumann, and
W F Fleck
June 1961,
Biochimica et biophysica acta,
C Wagner, and
K Eckardt, and
D Tresselt, and
W Ihn, and
G Schumann, and
W F Fleck
May 1996,
Gene,
C Wagner, and
K Eckardt, and
D Tresselt, and
W Ihn, and
G Schumann, and
W F Fleck
September 1980,
Applied and environmental microbiology,
C Wagner, and
K Eckardt, and
D Tresselt, and
W Ihn, and
G Schumann, and
W F Fleck
July 1990,
Journal of bacteriology,
C Wagner, and
K Eckardt, and
D Tresselt, and
W Ihn, and
G Schumann, and
W F Fleck
November 1951,
Antibiotics & chemotherapy (Northfield, Ill.),
