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

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Khokhar, Shahan
Feng, Yunjiang
Campitelli, Marc R
Ekins, Merrick G
Hooper, John NA
Beattie, Karren D
Sadowski, Martin C
Nelson, Colleen C
Davis, Rohan A
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2014
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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 lM.

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Bioorganic & Medicinal Chemistry Letters

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24

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15

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© 2016 Elsevier. Licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International Licence (http://creativecommons.org/licenses/by-nc-nd/4.0/) which permits unrestricted, non-commercial use, distribution and reproduction in any medium, providing that the work is properly cited.

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Medicinal and biomolecular chemistry

Biologically active molecules

Organic chemistry

Pharmacology and pharmaceutical sciences

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