Highly N-methylated linear peptides produced by an atypical sponge-derived Acremonium sp.
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.
Boot
Claudia M
CM
Department of Chemistry and Biochemistry and Department of Ocean Sciences, University of California, Santa Cruz, California 95064, USA.
Tenney
Karen
K
Valeriote
Frederick A
FA
Crews
Phillip
P
D000164:Acremonium / Q000737:chemistry*; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010219:Papua New Guinea; D054848:Peptaibols; D010455:Peptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011161:Porifera; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D054848:Peptaibols; D010455:Peptides; C508454:RHM1 peptide; C508455:RHM2 peptide; C508453:efrapeptin G