Neopikromycin and novapikromycin from the pikromycin biosynthetic pathway of Streptomyces venezuelae

J Nat Prod. 2006 May;69(5):847-9. doi: 10.1021/np060026p.

Abstract

Two new macrolides from the pikromycin biosynthetic pathway of Streptomyces venezuelae, neopikromycin (9) and novapikromycin (10), were identified and structurally characterized through mass spectrometry and NMR spectroscopy. The established structures showed that 9 and 10 have hydroxyl groups at C-14 (9) and at both C-12 and C-14 (10), on the basis of a comparison with narbomycin (7). The purified PikC cytochrome P450 monooxygenase catalyzes the in vitro hydroxylation of 7 and pikromycin (8) to yield 9 and 10, respectively, thus expanding the substrate- and regio-flexibility of this enzyme.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / isolation & purification
  • Anti-Bacterial Agents* / pharmacology
  • Bacillus subtilis / drug effects
  • Cytochrome P-450 Enzyme System / metabolism*
  • Macrolides* / chemistry
  • Macrolides* / isolation & purification
  • Macrolides* / metabolism
  • Macrolides* / pharmacology
  • Microbial Sensitivity Tests
  • Mixed Function Oxygenases / metabolism*
  • Molecular Structure
  • Streptomyces / chemistry*
  • Streptomyces / enzymology*
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Macrolides
  • neopikromycin
  • novapikromycin
  • Cytochrome P-450 Enzyme System
  • Mixed Function Oxygenases
  • PikC cytochrome P450 hydroxylase
  • picromycin