title: Isolation, structure determination and cytotoxicity studies of tryptophan alkaloids from an Australian marine sponge Hyrtios sp.
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.
authors: Eskitis Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, Australia.
authors: Shahan
authors: S
authors: Khokhar
authors: Eskitis Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, Australia.
authors: Yunjiang
authors: Y
authors: Feng
authors: Eskitis Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, Australia.
authors: Marc R
authors: MR
authors: Campitelli
authors: Queensland Museum, South Brisbane, QLD 4101, Australia.
authors: Merrick G
authors: MG
authors: Ekins
authors: Eskitis Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, Australia; Queensland Museum, South Brisbane, QLD 4101, Australia.
authors: John N A
authors: JN
authors: Hooper
authors: Eskitis Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, Australia.
authors: Karren D
authors: KD
authors: Beattie
authors: 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.
authors: Martin C
authors: MC
authors: Sadowski
authors: 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.
authors: Colleen C
authors: CC
authors: Nelson
authors: Eskitis Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, Australia. Electronic address: r.davis@griffith.edu.au.
authors: Rohan A
authors: RA
authors: Davis
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001315:Australia; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008958:Models, Molecular; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D011789:Quantum Theory; D013329:Structure-Activity Relationship; D014364:Tryptophan / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*
chemical_list: D000470:Alkaloids; D000970:Antineoplastic Agents; D014364:Tryptophan
keywords: Cytotoxicity; DFT-NMR; Hyrtios; Marine sponge; Tryptophan alkaloid