UBC Theses and Dissertations

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UBC Theses and Dissertations

Secondary metabolites from selected British Columbian marine organisms Tischler, Mark


The two purine alkaloids, phidolopin (36) and desmethylphidolopin (37), originally isolated from Phidolopora pacifica, were synthesized in order to produce sufficient quantities of the natural products for extended biological and pharmacological screening and to confirm the previous structural assignment of 37 which was based on spectral data. Various combinations of phidolopin (36), desmethylphidolopin (37), 4-hydroxymethyl-2-nitrophenol (38) and 4-methoxymethyl-2-nitrophenol (39) were isolated from four different species of bryozoans, Diaperoecia californica, Heteropora alaskensis, Tricellaria ternata and Hippodiplosia insculpta. A dietary origin is suggested for these metabolites. The red sponge, Anthoarcuata graceae yielded six novel steroids including the ∆⁴-3,6-diketosteroids 116, 117, the A-nor steroids anthosterone A (118) and anthosterone B (119) as well as two diosphenol containing steroids, 120 and 121. The proposed structures were based on a combination of spectral analysis, chemical interconversions, synthesis, and single crystal X-ray diffraction analysis.

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