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Natural Products Analysis of South Pacific Marine Sponges

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dc.rights.license Author Retains Copyright en_NZ
dc.contributor.advisor Northcote, Peter
dc.contributor.advisor Keyzers, Robert
dc.contributor.author Taufa, Taitusi
dc.date.accessioned 2018-04-19T22:21:40Z
dc.date.accessioned 2022-11-03T21:07:36Z
dc.date.available 2018-04-19T22:21:40Z
dc.date.available 2022-11-03T21:07:36Z
dc.date.copyright 2018
dc.date.issued 2018
dc.identifier.uri https://ir.wgtn.ac.nz/handle/123456789/30151
dc.description.abstract This thesis describes the isolation and structure elucidation of 15 new secondary metabolites from Tongan and New Zealand marine sponges. A total of 18 sponge specimens were subjected to an NMR-based screening method, of which four were analysed in detail. Examination of a two-sponge association, Stelletta crater and Desmacella dendyi from New Zealand, resulted in the isolation of two new 4-methylenesterols, craterols A (94) and B (95). To the best of the author’s knowledge, compounds 94 and 95 represent the first secondary metabolites to be reported from either species. Both 94 and 95 possess a double bond between C-5 and C-6, a feature that is unprecedented in this subgroup of marine natural products. An investigation of a Tongan sponge Zyzzya fuliginosa afforded two new pyrroloquinoline alkaloids, 6-bromodamirone B (182) and makaluvamine W (183). Makaluvamine W (183) contains an oxazole moiety, which is uncommon in this group of natural products. Both 182 and 183 lacked activity against the human promyelocytic leukemia cells (HL-60). Five new compounds were isolated from a Tongan sponge of the genus Leucetta, including two glycerol lipids (238 and 239), three glycerol ethers (244–246) and an imidazole alkaloid (243). Naamidine K (243) is a new addition to the naamidine family, while the glycerol metabolites are non-imidazole alkaloid additions to the group of compounds reported from this genus. A spectroscopic investigation into the Tongan sponge Cacospongia mycofijiensis yielded four new zampanolide analogues (282–285) and a new oxygenated sesquiterpene, isodictyodendrillin A (280). The isolation of the zampanolide analogues gives insight into the structure-activity relationship (SAR) in this family of compounds. Zampanolides B–D (282–284) displayed potent antiproliferative activity towards HL-60 cell lines in the low nanomolar range (3–5 nM), while zampanolide E (285) was significantly less potent with an IC50 value of 306 nM. In addition, the re-isolation of dactylolide (281) and zampanolide A (278) from this sponge, established a firm conclusion regarding the controversial configuration of dactylolide (281), which possesses the same absolute configuration as (–)-zampanolide A (278) and has a levorotatory optical rotation. en_NZ
dc.format pdf en_NZ
dc.language en_NZ
dc.language.iso en_NZ
dc.publisher Te Herenga Waka—Victoria University of Wellington en_NZ
dc.subject Marine natural products en_NZ
dc.subject NMR en_NZ
dc.subject Nuclear magnetic resonance en_NZ
dc.subject Zampanolides en_NZ
dc.title Natural Products Analysis of South Pacific Marine Sponges en_NZ
dc.type Text en_NZ
vuwschema.contributor.unit Centre for Biodiscovery en_NZ
vuwschema.contributor.unit School of Chemical and Physical Sciences en_NZ
vuwschema.subject.anzsrcfor 030502 Natural Products Chemistry en_NZ
vuwschema.subject.anzsrcseo 970103 Expanding Knowledge in the Chemical Sciences en_NZ
vuwschema.subject.anzsrctoa 1 Pure Basic Research en_NZ
vuwschema.type.vuw Awarded Doctoral Thesis en_NZ
thesis.degree.discipline Chemistry en_NZ
thesis.degree.grantor Te Herenga Waka—Victoria University of Wellington en_NZ
thesis.degree.level Doctoral en_NZ
thesis.degree.name Doctor of Philosophy en_NZ

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