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

Khokhar, Shahan and Feng, Yunjiang and Campitelli, Mark R. and Ekins, Merrick G. and Hooper, John N. A. and Beattie, Karren D. and Sadowski, Martin C. and 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.


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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Item Type: Article (Commonwealth Reporting Category C)
Refereed: Yes
Item Status: Live Archive
Additional Information: Published Version restricted in accordance with publisher copyright policy (Elsevier)
Faculty/School / Institute/Centre: No Faculty
Faculty/School / Institute/Centre: No Faculty
Date Deposited: 26 Oct 2014 05:20
Last Modified: 17 Mar 2015 01:06
Uncontrolled Keywords: tryptophan alkaloid; marine sponge; Hyrtios; DFT-NMR; cytotoxicity
Fields of Research (2008): 03 Chemical Sciences > 0306 Physical Chemistry (incl. Structural) > 030606 Structural Chemistry and Spectroscopy
03 Chemical Sciences > 0305 Organic Chemistry > 030502 Natural Products Chemistry
03 Chemical Sciences > 0307 Theoretical and Computational Chemistry > 030799 Theoretical and Computational Chemistry not elsewhere classified
11 Medical and Health Sciences > 1112 Oncology and Carcinogenesis > 111205 Chemotherapy
Fields of Research (2020): 34 CHEMICAL SCIENCES > 3403 Macromolecular and materials chemistry > 340399 Macromolecular and materials chemistry not elsewhere classified
34 CHEMICAL SCIENCES > 3405 Organic chemistry > 340502 Natural products and bioactive compounds
34 CHEMICAL SCIENCES > 3407 Theoretical and computational chemistry > 340799 Theoretical and computational chemistry not elsewhere classified
32 BIOMEDICAL AND CLINICAL SCIENCES > 3211 Oncology and carcinogenesis > 321105 Chemotherapy
Socio-Economic Objectives (2008): E Expanding Knowledge > 97 Expanding Knowledge > 970103 Expanding Knowledge in the Chemical Sciences
C Society > 92 Health > 9201 Clinical Health (Organs, Diseases and Abnormal Conditions) > 920102 Cancer and Related Disorders
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