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UBC Theses and Dissertations
Isolation, characterisation, and total synthesis of secondary metabolites from marine sponges Linington, Roger Gareth
Abstract
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]
Item Metadata
Title |
Isolation, characterisation, and total synthesis of secondary metabolites from marine sponges
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Creator | |
Publisher |
University of British Columbia
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Date Issued |
2004
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Description |
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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Extent |
11142699 bytes
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Genre | |
Type | |
File Format |
application/pdf
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Language |
eng
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Date Available |
2009-12-02
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Provider |
Vancouver : University of British Columbia Library
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Rights |
For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use.
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DOI |
10.14288/1.0061160
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URI | |
Degree | |
Program | |
Affiliation | |
Degree Grantor |
University of British Columbia
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Graduation Date |
2004-11
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Campus | |
Scholarly Level |
Graduate
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Aggregated Source Repository |
DSpace
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Rights
For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use.