Thuggacins, macrolide antibiotics active against Mycobacterium tuberculosis: isolation from myxobacteria, structure elucidation, conformation analysis and biosynthesis

Chemistry. 2007;13(20):5822-32. doi: 10.1002/chem.200700269.

Abstract

Two novel antibiotics, thuggacin A (1) and B (2), were isolated from the myxobacterium Sorangium cellulosum. 1 and 2 are unique thiazole-containing macrolides with side chains on both sides of the lactone group. Upon standing in solution, thuggacin A (1) rearranges by acyl migration of the lactone group to give a mixture with thuggacins B (2) and C (3). NOEs and vicinal coupling constants within the lactone ring provided distinct data for the generation of a structure model by PM3 calculations, which allowed an analysis of the conformation in solution and the relative configuration of six asymmetric centres. A minor sorangium metabolite was identified as 13-methyl-thuggacin A (4). Furthermore, two natural thuggacin variants, 5 and 6, were found in another myxobacterium, Chondromyces crocatus. In these variants, one side chain is replaced by a methyl group and a hydroxy group is repositioned to give a primary alcohol at the former methyl site, in an alpha position with respect to the thiazole ring. 1 proved to be active against clinical isolates and reference strains of Mycobacterium tuberculosis. Preliminary studies on the mechanism of action indicate inhibition of the cellular electron-transport chain.

MeSH terms

  • Antitubercular Agents / chemistry
  • Antitubercular Agents / isolation & purification*
  • Antitubercular Agents / metabolism
  • Macrolides / chemistry
  • Macrolides / isolation & purification*
  • Macrolides / metabolism
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Molecular Structure
  • Myxococcales / chemistry*
  • Myxococcales / metabolism

Substances

  • Antitubercular Agents
  • Macrolides
  • thuggacin A
  • thuggacin B
  • thuggacin C