Maggiemycin and anhydromaggiemycin: two novel anthracyclinone antitumor antibiotics. Isolation, structures, partial synthesis and biological properties.

R C Pandey, M W Toussaint, J C McGuire, M C Thomas

NCI-FCRF Fermentation Program, NCI-Frederick Cancer Research Facility, Maryland 21701.

The Journal of antibiotics 1989 Nov

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Two new anthracyclinone antitumor antibiotics, maggiemycin (6, NSC-D344012) and anhydromaggiemycin (8) have been isolated from a culture of an unspeciated Streptomyces (ATCC No. 39235). Bioautography against Bacillus subtilis was used for the preliminary detection of these anthracyclinones. Structures were proposed based on their UV-visible, IR, 1H NMR, 13C NMR spectra, electron impact (EI) and high-resolution EI-MS and confirmed by partial synthesis and a direct correlation with epsilon-rhodomycinone. Both the anthracyclinones are active against KB, P388 and L1210 murine tumor cell lines; however, anhydromaggiemycin was more active than maggiemycin. A number of related anthracyclinones have also been prepared and their biological activity has been determined. The structure-activity relationship of these new anthracyclinones is also discussed.

Citation

R C Pandey, M W Toussaint, J C McGuire, M C Thomas. Maggiemycin and anhydromaggiemycin: two novel anthracyclinone antitumor antibiotics. Isolation, structures, partial synthesis and biological properties. The Journal of antibiotics. 1989 Nov;42(11):1567-77