New betaclamycin and aclarubicin analogs obtained by prolonged microbial conversion with an aclarubicin-negative mutant.
Microbial conversion of beta-rhodomycinone and aklavinone using an aclarubicin-negative Streptomyces galilaeus mutant afforded new anthracycline antibiotics CG21-C and CG1-C which had a rednosyl-2-deoxyfucosyl-rhodosaminyl trisaccharide residue at C-7 of each added aglycone. They were produced only when a prolonged conversion culture took place. Because the usual conversion products containing a cinerulosyl-2-deoxyfucosyl-rhodosaminyl residue were at first accumulated and then decreased during further cultivation, it was evident that they occurred by the modification of terminal cinerulose. The isolation, purification, and structural determination are described, and cytotoxicity in vitro against cultured L1210 cells and the formation mechanism are discussed.
Johdo
O
O
Central Research Laboratories, Mercian Corporation, Fujisawa, Japan.
Yoshioka
T
T
Naganawa
H
H
Takeuchi
T
T
Yoshimoto
A
A
D015250:Aclarubicin / Q000031:analogs & derivatives*; D000818:Animals; D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic / Q000737:chemistry* / Q000378:metabolism* / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D015394:Molecular Structure; D009154:Mutation; D013302:Streptomyces / Q000235:genetics / Q000378:metabolism*; D014407:Tumor Cells, Cultured
D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic; C101445:CG1-C antibiotic; C101446:CG21-C antibiotic; C076090:betaclamycin B; D015250:Aclarubicin; C042911:betaclamycin A