Chromophenazines from the terrestrial Streptomyces sp. Ank 315

J Nat Prod. 2012 Jan 27;75(1):2-8. doi: 10.1021/np100818d. Epub 2012 Jan 5.

Abstract

The new chromophenazines A-F [9-methyl-5-(3'-methylbut-2'-enyl)-5H-benzo[a]phenazin-7-one (1a), 9-methyl-5-(3'-methylbut-2'-enyl)-7-oxo-5,7-dihydrobenzo[a]phenazine-1-carboxylic acid (1b), 5-(3'-methylbut-2'-enyl)-7-oxo-5,7-dihydrophenazine-1-carboxamide (2), 3-benzoyl-5-(3'-methylbut-2'-enyl)-5,10-dihydrophenazine-1-carboxylic acid (5a), 3,7-dibenzoyl-5-(3'-methylbut-2'-enyl)-5,10-dihydrophenazine-1-carboxylic acid (5b), and 3,7-dibenzoyl-5-(3'-methylbut-2'-enyl)-5,10-dihydrophenazine-1-carboxamide (5c)], together with phenazine-1-carboxylic acid, 1-phenazinecarboxamide, 1-phenazinol, tryptophol, and anthranilic acid, were isolated from Streptomyces sp. Ank 315. The structures of the new compounds were established on the basis of spectroscopic data, 1D NOE, 2D NMR, and ESIMS measurements and comparison with literature values.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / isolation & purification*
  • Anti-Infective Agents / pharmacology
  • Bacillus subtilis / drug effects
  • Candida albicans / drug effects
  • Escherichia coli / drug effects
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Mucor / drug effects
  • Nuclear Magnetic Resonance, Biomolecular
  • Phenazines / chemistry
  • Phenazines / isolation & purification*
  • Phenazines / pharmacology
  • Staphylococcus aureus / drug effects
  • Streptomyces / chemistry*

Substances

  • Anti-Infective Agents
  • Phenazines
  • chromophenazine D