JBIR-78 and JBIR-95: phenylacetylated peptides isolated from Kibdelosporangium sp. AK-AA56

J Nat Prod. 2012 Feb 24;75(2):280-4. doi: 10.1021/np2008279. Epub 2012 Jan 20.

Abstract

The search for metabolites of Kibdelosporangium sp. AK-AA56 resulted in the discovery of novel N-phenylacetylated peptides, JBIR-78 (1) and JBIR-95 (2). Compounds 1 and 2 were established to be N-phenylacetylated heptapeptides by extensive NMR and HRESIMS analyses. The absolute configuration of the standard amino acids including a cysteic acid moiety was determined using Marfey's method on the acid hydrolysates of 1 and 2. The relative and absolute configurations of a nonstandard amino acid, β-hydroxyleucine, were elucidated using the J-based and modified Mosher's methods, respectively. In an antimicrobial test, 1 showed antibacterial activity against Micrococcus luteus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Actinomycetales / chemistry*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Japan
  • Microbial Sensitivity Tests
  • Micrococcus / drug effects
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Peptides / chemistry
  • Peptides / isolation & purification*
  • Peptides / pharmacology

Substances

  • Anti-Bacterial Agents
  • JBIR-78
  • JBIR-95
  • Peptides