APHE-1 and APHE-2, two new antimicrobial and cytotoxic antibiotics. II. Physico-chemical properties and structure elucidation.

  title={APHE-1 and APHE-2, two new antimicrobial and cytotoxic antibiotics. II. Physico-chemical properties and structure elucidation.},
  author={M. Fidalgo and M. Arias and J. Soliveri and M. Arias},
  journal={The Journal of antibiotics},
  volume={45 11},
Two new pyrazolo-isoquinolinone antibiotics, APHE-1 and APHE-2, have been isolated from the culture filtrate and mycelia of Streptoverticillium griseocarneum NCIMB 40447. Molecular formulae were established as C13H12N2O for APHE-1 and C14H14N2O for APHE-2, by elemental analysis, NMR and mass spectra. 2D NMR techniques (1H-1H COSY-45 and 1H-13C correlated spectroscopy) have been applied to establish their structures. 
APHE-1 and APHE-2, two new antimicrobial and cytotoxic antibiotics. I. Taxonomy, fermentation, isolation and biological activity.
APHE-1 and APHE-2 are two new antibiotics produced by Streptoverticillium griseocarneum NCIMB 40447. They exhibited a remarkable cytotoxic activity against several tumor cell lines from differentExpand
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APHE-3, a spore-associated antibiotic of Streptomyces griseocarneus NCIMB 40447
Solid cultures of the producing strain grown on Bennett medium develop abundant mycelium and intense sporulation, and APHE compounds are present in almost all streptomycetes tested, indicating a possible role in the life cycle of these microorganisms. Expand
Nutritional requirements for the production of pyrazoloisoquinolinone antibiotics by Streptomyces griseocarneus NCIMB 40447
Results obtained in minimal medium supplemented with l-valine and l-histidine indicate a relationship between these amino acids and APHE biosynthesis and show possible links with fatty acid biosynthesis. Expand
Structure revision of the APHEs through synthesis
An attempt to synthesize APHE-3 (3-methylpyrazolo[1,5-b]isoquinolin-9(1H)-one, 3) gave the tautomer 3-methylpyrazolo[1,5-b]isoquinolin-9(4H)-one (9) instead, and led to a reconsideration of theExpand
Total Synthesis of a Novel Isoquinolinone Alkaloid Marinamide and its Methyl Ester
A naturally occurring isoquinolinone alkaloid marinamide and its methyl ester were synthesised from phthalic anhydride over eight steps in 46% and 52% overall yield. The key intermediate methylExpand
Chlorosulfonic acid-mediated cyclization of 4-phenyl-3-isocoumarincarboxylic acids and 4-phenyl-3-isoquinolinonecarboxylic acids: an efficient synthesis of 3-oxoindeno[2,1-c]isocoumarins and 3-oxoindeno[2,1-c]isoquinolinones
A highly efficient and clean method has been developed for the synthesis of 3-oxoindeno[2,1-c]isocoumarins and 3-oxoindeno[2,1-c]isoquinolinones from 4-phenyl-3-isocoumarincarboxylic acids andExpand
Selective synthesis of N-substituted pyrrolo[1,2-a]pyrazin-1(2H)-one derivatives via alkyne cyclization
Abstract A novel and efficient synthesis of N-substituted pyrrolo-pyrazinone derivatives has been developed. A trichloroacetyl group connected to the pyrrole ring was converted into the desiredExpand
Optimization of fermentation parameters for enhanced APHE production from Streptomyces griseocarneus through submerged fermentation
Increasing resistance of microbes against antimicrobial drugs keep scientists busy in exploring novel and potent antibiotics. The present study is concerned with the production of antitumorExpand
Factors affecting protoplast formation and regeneration in three strains of Streptoverticillium
Maximum cell regeneration was achieved with protoplasts obtained from mid-exponential growth phase mycelia and plated on an undehydrated Bennet agar overlayered with the same medium containing a lower agar concentration. Expand