Septocylindrins A and B: peptaibols produced by the terrestrial fungus Septocylindrium sp. LL-Z1518.
Two new peptaibols, septocylindrin A (1) and septocylindrin B (2), related to the well-studied membrane-channel-forming peptaibol alamethicin, were obtained from a terrestrial isolate of the fungus Septocylindrium sp. Both 1 and 2 are linear 19-amino acid peptides with a modified phenylalanine C-terminus. Analysis of the HRMS data indicated that they differ only in the 18th residue, where 1 contains Glu and 2 contains Gln. The structures of these two peptaibols were determined by extensive NMR and HRMS analysis. The absolute configurations of amino acids present in 1 were determined using Marfey's methodology. Both compounds were isolated through bioassay-guided fractionation and exhibited significant antibacterial and antifungal activity.
Summers
Mia Y
MY
Department of Chemical and Screening Sciences, Wyeth Research, 401 N. Middletown Road, Pearl River, NY 10965, USA. summerm@wyeth.com
Kong
Fangming
F
Feng
Xidong
X
Siegel
Marshall M
MM
Janso
Jeffrey E
JE
Graziani
Edmund I
EI
Carter
Guy T
GT
D000408:Alamethicin / Q000737:chemistry; D000595:Amino Acid Sequence; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005658:Fungi / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D008969:Molecular Sequence Data; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D054848:Peptaibols; D010455:Peptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D054848:Peptaibols; D010455:Peptides; C519245:septocylindrin A; C519246:septocylindrin B; D000408:Alamethicin