Rifamorpholines A-E, potential antibiotics from locust-associated actinobacteria Amycolatopsis sp. Hca4

Org Biomol Chem. 2017 May 10;15(18):3909-3916. doi: 10.1039/c7ob00614d.

Abstract

Cultivation of locust associated rare actinobacteria, Amycolatopsis sp. HCa4, has provided five unusual macrolactams rifamorpholines A-E. Their structures were determined by interpretation of spectroscopic and crystallographic data. Rifamorpholines A-E possess an unprecedented 5/6/6/6 ring chromophore, representing a new subclass of rifamycin antibiotics. The biosynthetic pathway for compounds 1-5 involves a key 1,6-cyclization for the formation of the morpholine ring. Compounds 2 and 4 showed potent activities against methicillin-resistant Staphylococcus aureus (MRSA) with MICs of 4.0 and 8.0 μM, respectively.

MeSH terms

  • Actinobacteria / metabolism*
  • Animals
  • Anti-Bacterial Agents / biosynthesis
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology*
  • Grasshoppers / microbiology*
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Conformation
  • Morpholines / chemistry*
  • Morpholines / metabolism
  • Morpholines / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Morpholines