Highly N-methylated linear peptides produced by an atypical sponge-derived Acremonium sp

J Nat Prod. 2006 Jan;69(1):83-92. doi: 10.1021/np0503653.

Abstract

RHM1 (1) and RHM2 (2) are highly N-methylated linear octapeptides produced by an atypical strain of Acremonium sp., cultured from a marine sponge collected in Papua New Guinea. The known peptaibiotic efrapeptin G (3) was also isolated from this fungus. The planar structures of 1 and 2 were assigned based on 1D- and 2D-NMR experiments and fragmentation patterns from ESIMS. The absolute configuration of 1 was determined via Marfey's method; the absolute configuration of 2 is proposed to be identical. Efrapeptin G (3) displayed potent cytotoxicity against murine cancer cell lines, while RHM1 (1) and RHM2 (2) showed weak cytotoxicity against murine cancer cell lines; efrapeptin G (3) and RHM1 (1) also demonstrated antibacterial activity.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Acremonium / chemistry*
  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Drug Screening Assays, Antitumor
  • Mice
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Papua New Guinea
  • Peptaibols
  • Peptides / chemistry
  • Peptides / isolation & purification*
  • Peptides / pharmacology
  • Porifera
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Peptaibols
  • Peptides
  • RHM1 peptide
  • RHM2 peptide
  • efrapeptin G