Isolation,structure determination and cytotoxicity studies of tryptophan alkaloids from an Australian marine sponge Hyrtios sp. |
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| Affiliation: | 1. Eskitis Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, Australia;2. Queensland Museum, South Brisbane, QLD 4101, Australia;3. 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;2. Department of Pathology and Molecular Medicine, Queen''s University, Kingston, Ontario, Canada;1. Department of Microbiology and Cell Biology, Tokyo Metropolitan Institute of Medical Science, 2-1-6 Kamikitazawa, Setagaya-ku, Tokyo 156-8506, Japan;2. Department of Microbiology, Graduate School of Medicine, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan;3. Department of Virology II, National Institute of Infectious Diseases, 1-23-1 Toyama, Shinjuku-ku, Tokyo 162-8640, Japan;4. Institute of Microbial Chemistry, 3-14-23 Kamiohsaki, Shinagawa-ku, Tokyo 141-0021, Japan |
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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 μM. |
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| Keywords: | Tryptophan alkaloid Marine sponge DFT-NMR Cytotoxicity |
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