Pterulamides I-VI, linear peptides from a Malaysian Pterula sp.

Gerhard Lang, Maya I. Mitova, Anthony L J Cole, Laily B. Din, Sabaratnam Vikineswary, Noorlidah Abdullah, John W. Blunt, Murray H G Munro

    Research output: Contribution to journalArticle

    9 Citations (Scopus)

    Abstract

    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 μg/mL (0.79 and 1.33 μM), respectively.

    Original languageEnglish
    Pages (from-to)1389-1393
    Number of pages5
    JournalJournal of Natural Products
    Volume69
    Issue number10
    DOIs
    Publication statusPublished - Oct 2006

    Fingerprint

    Pterula
    peptides
    Amino Acids
    Peptides
    amino acids
    fruiting bodies
    Inhibitory Concentration 50
    inhibitory concentration 50
    Cells
    cell lines
    Nuclear magnetic resonance
    Cell Line
    Acids
    acids
    Experiments
    methodology

    ASJC Scopus subject areas

    • Plant Science
    • Chemistry (miscellaneous)
    • Drug Discovery
    • Organic Chemistry
    • Pharmacology

    Cite this

    Lang, G., Mitova, M. I., Cole, A. L. J., Din, L. B., Vikineswary, S., Abdullah, N., ... Munro, M. H. G. (2006). Pterulamides I-VI, linear peptides from a Malaysian Pterula sp. Journal of Natural Products, 69(10), 1389-1393. https://doi.org/10.1021/np0600245

    Pterulamides I-VI, linear peptides from a Malaysian Pterula sp. / Lang, Gerhard; Mitova, Maya I.; Cole, Anthony L J; Din, Laily B.; Vikineswary, Sabaratnam; Abdullah, Noorlidah; Blunt, John W.; Munro, Murray H G.

    In: Journal of Natural Products, Vol. 69, No. 10, 10.2006, p. 1389-1393.

    Research output: Contribution to journalArticle

    Lang, G, Mitova, MI, Cole, ALJ, Din, LB, Vikineswary, S, Abdullah, N, Blunt, JW & Munro, MHG 2006, 'Pterulamides I-VI, linear peptides from a Malaysian Pterula sp.', Journal of Natural Products, vol. 69, no. 10, pp. 1389-1393. https://doi.org/10.1021/np0600245
    Lang G, Mitova MI, Cole ALJ, Din LB, Vikineswary S, Abdullah N et al. Pterulamides I-VI, linear peptides from a Malaysian Pterula sp. Journal of Natural Products. 2006 Oct;69(10):1389-1393. https://doi.org/10.1021/np0600245
    Lang, Gerhard ; Mitova, Maya I. ; Cole, Anthony L J ; Din, Laily B. ; Vikineswary, Sabaratnam ; Abdullah, Noorlidah ; Blunt, John W. ; Munro, Murray H G. / Pterulamides I-VI, linear peptides from a Malaysian Pterula sp. In: Journal of Natural Products. 2006 ; Vol. 69, No. 10. pp. 1389-1393.
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