2. Academic Validation
  3. Isolation, structure determination and cytotoxicity studies of tryptophan alkaloids from an Australian marine sponge Hyrtios sp

Isolation, structure determination and cytotoxicity studies of tryptophan alkaloids from an Australian marine sponge Hyrtios sp

  • Bioorg Med Chem Lett. 2014 Aug 1;24(15):3329-32. doi: 10.1016/j.bmcl.2014.05.104.
Shahan Khokhar 1,  Yunjiang Feng 1,  Marc R Campitelli 1,  Merrick G Ekins 2,  John N A Hooper 3,  Karren D Beattie 1,  Martin C Sadowski 4,  Colleen C Nelson 4,  Rohan A Davis 5
Affiliations

Affiliations

  • 1 Eskitis Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, Australia.
  • 2 Queensland Museum, South Brisbane, QLD 4101, Australia.
  • 3 Eskitis Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, Australia; Queensland Museum, South Brisbane, QLD 4101, Australia.
  • 4 Australian Prostate Cancer Research Centre-Queensland Institute of Health and Biomedical Innovation, Queensland University of Technology, Princess Alexandra Hospital, Translational Research Institute, Brisbane, QLD 4102, Australia.
  • 5 Eskitis Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, Australia. Electronic address: r.davis@griffith.edu.au.
PMID: 24973030 DOI: 10.1016/j.bmcl.2014.05.104
Abstract

Mass-guided fractionation of the MeOH extract from a specimen of the Australian marine Sponge Hyrtios sp. resulted in the isolation of two new tryptophan Alkaloids, 6-oxofascaplysin (2), and secofascaplysic acid (3), in addition to the known metabolites fascaplysin (1) and reticulatate (4). The structures of all molecules were determined following NMR and MS data analysis. Structural ambiguities in 2 were addressed through comparison of experimental and DFT-generated theoretical NMR spectral values. Compounds 1-4 were evaluated for their cytotoxicity against a prostate Cancer cell line (LNCaP) and were shown to display IC50 values ranging from 0.54 to 44.9 μM.

Keywords

Cytotoxicity; DFT-NMR; Hyrtios; Marine sponge; Tryptophan alkaloid.

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