Pteratides I-IV, new cytotoxic cyclodepsipeptides from the Malaysian basidiomycete Pterula sp.

Chien Hui Chen, Gerhard Lang, Maya I. Mitova, Annabel C. Murphy, Anthony L J Cole, Laily B. Din, John W. Blunt, Murray H G Munro

    Research output: Contribution to journalArticle

    9 Citations (Scopus)

    Abstract

    Four new cyclodepsipeptides, pteratides I-IV (1-4), have been isolated from the extract of a Pterula species collected from a Malaysian tropical forest. Homonuclear and heteronuclear 2D NMR techniques as well as MS fragmentation experiments, in combination with methanolysis, determined the gross structures of the peptides and showed that pteratides I and II each contained the nonproteinogenic amino acid 4-methylproline. The absolute configurations of the amino acids in pteratides I-IV were established using Marfey's method. Pteratides I and II are each potently cytotoxic against the P388 murine leukemia cell line (IC50 values of 41 and 40 nM, respectively). Pteratides III and IV show weaker, but still notable, activity with IC50 values of 7.4 and 2.9 μM, respectively.

    Original languageEnglish
    Pages (from-to)7947-7951
    Number of pages5
    JournalJournal of Organic Chemistry
    Volume71
    Issue number21
    DOIs
    Publication statusPublished - 13 Oct 2006

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    Depsipeptides
    Amino Acids
    Cells
    Nuclear magnetic resonance
    Peptides
    Experiments
    4-methylproline

    ASJC Scopus subject areas

    • Organic Chemistry

    Cite this

    Chen, C. H., Lang, G., Mitova, M. I., Murphy, A. C., Cole, A. L. J., Din, L. B., ... Munro, M. H. G. (2006). Pteratides I-IV, new cytotoxic cyclodepsipeptides from the Malaysian basidiomycete Pterula sp. Journal of Organic Chemistry, 71(21), 7947-7951. https://doi.org/10.1021/jo060843u

    Pteratides I-IV, new cytotoxic cyclodepsipeptides from the Malaysian basidiomycete Pterula sp. / Chen, Chien Hui; Lang, Gerhard; Mitova, Maya I.; Murphy, Annabel C.; Cole, Anthony L J; Din, Laily B.; Blunt, John W.; Munro, Murray H G.

    In: Journal of Organic Chemistry, Vol. 71, No. 21, 13.10.2006, p. 7947-7951.

    Research output: Contribution to journalArticle

    Chen, CH, Lang, G, Mitova, MI, Murphy, AC, Cole, ALJ, Din, LB, Blunt, JW & Munro, MHG 2006, 'Pteratides I-IV, new cytotoxic cyclodepsipeptides from the Malaysian basidiomycete Pterula sp.', Journal of Organic Chemistry, vol. 71, no. 21, pp. 7947-7951. https://doi.org/10.1021/jo060843u
    Chen, Chien Hui ; Lang, Gerhard ; Mitova, Maya I. ; Murphy, Annabel C. ; Cole, Anthony L J ; Din, Laily B. ; Blunt, John W. ; Munro, Murray H G. / Pteratides I-IV, new cytotoxic cyclodepsipeptides from the Malaysian basidiomycete Pterula sp. In: Journal of Organic Chemistry. 2006 ; Vol. 71, No. 21. pp. 7947-7951.
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    abstract = "Four new cyclodepsipeptides, pteratides I-IV (1-4), have been isolated from the extract of a Pterula species collected from a Malaysian tropical forest. Homonuclear and heteronuclear 2D NMR techniques as well as MS fragmentation experiments, in combination with methanolysis, determined the gross structures of the peptides and showed that pteratides I and II each contained the nonproteinogenic amino acid 4-methylproline. The absolute configurations of the amino acids in pteratides I-IV were established using Marfey's method. Pteratides I and II are each potently cytotoxic against the P388 murine leukemia cell line (IC50 values of 41 and 40 nM, respectively). Pteratides III and IV show weaker, but still notable, activity with IC50 values of 7.4 and 2.9 μM, respectively.",
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    AU - Din, Laily B.

    AU - Blunt, John W.

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