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

J Antibiot (Tokyo). 1989 Nov;42(11):1567-77. doi: 10.7164/antibiotics.42.1567.

Abstract

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.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Anthracyclines
  • Antibiotics, Antineoplastic / chemical synthesis
  • Antibiotics, Antineoplastic / isolation & purification*
  • Antibiotics, Antineoplastic / pharmacology
  • Chromatography, Thin Layer
  • Drug Screening Assays, Antitumor
  • Fermentation
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Naphthacenes
  • Spectrophotometry
  • Streptomyces / metabolism
  • Tumor Cells, Cultured

Substances

  • Anthracyclines
  • Antibiotics, Antineoplastic
  • Naphthacenes
  • rhodomycinone
  • maggiemycin
  • anhydromaggiemycin
  • daunomycinone