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UBC Theses and Dissertations

Isolation, characterisation, and total synthesis of secondary metabolites from marine sponges Linington, Roger Gareth


Investigations into the chemistry of the marine sponge Caminus sphaeroconia have led to the isolation of the glycolipids caminosides A - D (35, 42, 43, 44). Bioassay guided fractionation showed this class of compounds to be active in a screen designed to identify type III secretion inhibitors. The type III secretion system is the mechanism by which a number of pathogenic bacteria achieve invasion of target human host cells. Compounds capable of disrupting the type III secretion system have the potential to eliminate this pathogenic behaviour, and it has been proposed that small molecules exhibiting this activity could find future utility as antibacterial therapeutics [Chemical Diagram] Previous investigations into the chemistry of the marine sponge Stylissa carteri led to the isolation of two novel alkaloids, latonduines A and B (66 and 67). The paucity of structural information provided by one- and two-dimensional NMR experiments and mass spectrometric analyses allowed only a tentative structural assignment to be made. Completion of a total synthesis of 66 has confirmed the proposed structure and provided material for further biological testing. [Chemical Diagram] Despite structural similarities with a number of previously reported biologically active marine alkaloids, 66 exhibited no biological activity against a range of protein kinases. In an attempt to generate a novel protein kinase inhibitor by rational drug design, synthesis of a regioisomer of 66, isolatonduine A (70), was attempted. Progress towards the synthesis of 70 will be presented. [Chemical Diagram]

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