University of Canterbury Home
    • Admin
    UC Research Repository
    UC Library
    JavaScript is disabled for your browser. Some features of this site may not work without it.
    View Item 
    1. UC Home
    2. Library
    3. UC Research Repository
    4. Faculty of Science | Te Kaupeka Pūtaiao
    5. Science: Theses and Dissertations
    6. View Item
    1. UC Home
    2.  > 
    3. Library
    4.  > 
    5. UC Research Repository
    6.  > 
    7. Faculty of Science | Te Kaupeka Pūtaiao
    8.  > 
    9. Science: Theses and Dissertations
    10.  > 
    11. View Item

    Potential anti-tumour compounds from marine sources (1989)

    Thumbnail
    View/Open
    copp_thesis.pdf (6.480Mb)
    Type of Content
    Theses / Dissertations
    UC Permalink
    http://hdl.handle.net/10092/8568
    http://dx.doi.org/10.26021/5992
    
    Thesis Discipline
    Chemistry
    Degree Name
    Doctor of Philosophy
    Publisher
    University of Canterbury. Chemistry
    Collections
    • Science: Theses and Dissertations [4497]
    Authors
    Copp, Brent R.
    show all
    Abstract

    The search for potential anti-tumour compounds from marine sources has covered many areas of research. Initial investigations were made to ascertain any drug mode of action information contained in the readings of our in-house antiviral/cytotoxicity assays. These results, utilising clinical drugs with known modes of action, failed to indicate any obvious correlations. The extract of a New Zealand ascidian, Aplidium species D, was studied because extracts prepared from it always exhibited a wide range of biological activities. Bioassay directed fractionation led to the isolation of a novel metabolite cis-5-hydroxy-4-(4'-hydroxy-3'-methoxyphenyl)-4-(2"-imidazolyl)-1,2,3-trithiane, trithiane A. The structure was solved by extensive use of mass and NMR spectroscopy. The compound was found to be stable in acidified solutions, but under alkaline conditions was observed to interconvert to the 4-epi derivative, trithiane B and to decompose to 2-vanilloyl imidazole. Two competing base catalysed mechanisms were proposed to account for these observations. The relative stereochemistries of trithiane A and B were established by ¹H NMR NOE experiments, application of the modified Karplus equation and molecular mechanics modelling. Numerous attempts were made to crystallise trithiane A and to make crystalline derivatives. Only one reaction, oxidation to the monosulphoxide, gave any isolable products. The trithianes were found to be cytotoxic to both BSC monkey kidney cells and P388 leukemia cells and modestly inhibitory to bacteria and fungi. No efficacy against in vitro viruses was observed. A study based upon the chemical modification of discorhabdin C was carried out in order to produce compounds with more effective in vivo activity than discorhabdin C and to explore the structural features that could be responsible for the observed bioactivities of the discorhabdins. To this end, a new discorhabdin, E, was isolated and identified and six new derivatives were synthesised and characterised. Analysis of the biological activities of the discorhabdin derivatives suggested that structural features of ring E and possibly electron distribution changes in the iminoquinone moiety were responsible for the observed bioactivities.

    Rights
    Copyright Brent R. Copp
    https://canterbury.libguides.com/rights/theses

    Related items

    Showing items related by title, author, creator and subject.

    • Actinomycetes and fungi associated with marine invertebrates: a potential source of bioactive compounds 

      Mahyudin, Nor Ainy (University of Canterbury. Biological Sciences, 2008)
      Actinomycetes and fungi were successfully isolated from both New Zealand and Malaysian marine invertebrates and classified as facultatively marine based on their ability to grow on both sea water and non-sea water media. ...
    • An investigation into the anti-tumour properties of resveratrol against ovarian cancer using the CAM model. 

      Singh, Melanie Gabrielle (University of Canterbury, 2019)
      Ovarian cancer is one of the deadliest gynaecological cancers. A key contributing factor to its high mortality rate is its non-specific symptoms and lack of early detection, which results in most patients being diagnosed ...
    • Anti-tumour effects of resveratrol and pterostilbene on ovarian cancer. 

      Hosking, Janelle (University of Canterbury, 2016)
      Ovarian cancer is the most lethal gynaecologic malignancy, with a high mortality rate that is associated with the difficulty of treating the disease. This is due to the typical onset of symptoms when the disease is at a ...
    Advanced Search

    Browse

    All of the RepositoryCommunities & CollectionsBy Issue DateAuthorsTitlesSubjectsThesis DisciplineThis CollectionBy Issue DateAuthorsTitlesSubjectsThesis Discipline

    Statistics

    View Usage Statistics
    • SUBMISSIONS
    • Research Outputs
    • UC Theses
    • CONTACTS
    • Send Feedback
    • +64 3 369 3853
    • ucresearchrepository@canterbury.ac.nz
    • ABOUT
    • UC Research Repository Guide
    • Copyright and Disclaimer
    • SUBMISSIONS
    • Research Outputs
    • UC Theses
    • CONTACTS
    • Send Feedback
    • +64 3 369 3853
    • ucresearchrepository@canterbury.ac.nz
    • ABOUT
    • UC Research Repository Guide
    • Copyright and Disclaimer