Pterulamides I-VI, linear peptides from a Malaysian Pterula sp.
Six new linear peptides, pterulamides I-VI (1-6), were isolated from the fruiting bodies of a Malaysian Pterula species. The structures were elucidated by MS and 2D NMR experiments, and the absolute configurations of the constituent amino acids established using Marfey's method. The pterulamides are mainly assembled from nonpolar N-methylated amino acids and, most interestingly, have non-amino-acid N-terminal groups, among them the unusual cinnamoyl, (E)-3-methylsulfinylpropenoyl, and (E)-3-methylthiopropenoyl groups. Furthermore, pterulamides I-V are the first natural peptides with a methylamide C-terminus. Pterulamides I and IV are cytotoxic against the P388 cell line with IC50 values of 0.55 and 0.95 microg/mL (0.79 and 1.33 microM), respectively.
Lang
Gerhard
G
Department of Chemistry and School of Biological Sciences, University of Canterbury, Christchurch, New Zealand.
Mitova
Maya I
MI
Cole
Anthony L J
AL
Din
Laily B
LB
Vikineswary
Sabaratnam
S
Abdullah
Noorlidah
N
Blunt
John W
JW
Munro
Murray H G
MH
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001487:Basidiomycota / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D007941:Leukemia P388; D008296:Malaysia; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009842:Oligopeptides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
D000970:Antineoplastic Agents; D009842:Oligopeptides