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

Article


Khokhar, Shahan, Feng, Yunjiang, Campitelli, Mark R., Ekins, Merrick G., Hooper, John N. A., Beattie, Karren D., Sadowski, Martin C., Nelson, Colleen C. and Davis, Rohan A.. 2014. "Isolation, structure determination and cytotoxicity studies of tryptophan alkaloids from an Australian marine sponge Hyrtios sp." Bioorganic and Medicinal Chemistry Letters. 24 (15), pp. 3329-3332. https://doi.org/10.1016/j.bmcl.2014.05.104
Article Title

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

ERA Journal ID1566
Article CategoryArticle
AuthorsKhokhar, Shahan (Author), Feng, Yunjiang (Author), Campitelli, Mark R. (Author), Ekins, Merrick G. (Author), Hooper, John N. A. (Author), Beattie, Karren D. (Author), Sadowski, Martin C. (Author), Nelson, Colleen C. (Author) and Davis, Rohan A. (Author)
Journal TitleBioorganic and Medicinal Chemistry Letters
Journal Citation24 (15), pp. 3329-3332
Number of Pages4
Year2014
PublisherElsevier
ISSN0960-894X
1464-3405
Digital Object Identifier (DOI)https://doi.org/10.1016/j.bmcl.2014.05.104
Web Address (URL)http://www.ncbi.nlm.nih.gov/pubmed/24973030
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.

Keywordstryptophan alkaloid; marine sponge; Hyrtios; DFT-NMR; cytotoxicity
ANZSRC Field of Research 2020340399. Macromolecular and materials chemistry not elsewhere classified
340502. Natural products and bioactive compounds
340799. Theoretical and computational chemistry not elsewhere classified
321105. Chemotherapy
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Byline AffiliationsGriffith University
Queensland Museum, Australia
Australian Prostate Cancer Research Centre, Australia
Queensland University of Technology
Institution of OriginUniversity of Southern Queensland
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