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

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.

• Authors: Claudia M Boot, Karen Tenney, Frederick A Valeriote, Phillip Crews
• Journal: Journal of natural products (J Nat Prod) Vol. 69 Issue 1 Pg. 83-92 (Jan 2006) ISSN: 0163-3864 [Print] United States
• PMID: 16441074 (Publication Type: Journal Article, Research Support, N.I.H., Extramural)

Chemical References

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

Topics

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