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Major metabolites produced by the Papua New Guinean Porifera Monanchora sp. and South African kelp Ecklonia sp.

Buyukdag, Mehmet
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https://hdl.handle.net/10379/18421
 https://doi.org/10.13025/29215
Publication Date
2024-12-19
Keywords
Natural Product, Marine Biodiscovery, Polycyclic Guanidine Alkaloids, Cyclic Guanidine Alkaloids, Batzelladines, Crambescins, Crambescidins, Porifera, Kelp, Sponge, Seaweeed, Papua New Guinea, PNG, South Africa, Phlorotannin, Sulfated Phlorotannins, Method Development, Monanchora, Ecklonia, Science, Biological and Chemical Sciences, Chemistry
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master thesis
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Abstract
Chapter 1: Sponges from the genus Monanchora are renowned sources of bioactive cyclic guanidine alkaloids. Monanchora from Papua New Guinea are understudied and may represent a new species. The aim of this chapter was to explore the chemical diversity within a Monanchora sample collected from Papua New Guinea. Using computational analysis of the positive mode High Resolution-Electron Spray Ionisation-Tandem Mass Spectrum ((+)-HR-ESI-MS-MS) of the methanolic extract, 4 known pentacyclic guanidines, crambescidin acid, crambescidic acid, crambescidin 359 and 16βhydroxycrambescidin 359 were identified, along with 3 known primary metabolites, phosphatidylethanolamine (16:1/15:0 or 15:1/16:0), lyso-C18-PAF and 1-16: O-lyso-PC, were identified. Through RP-HPLC purification, UPLC-MS analysis and 1D/2D NMR structure elucidation, 2 new cyclic guanidine alkaloids, P2RP1-227 and P2RP2-227 and a known biyclic guanidine, dehydrocrambine A was isolated. The discovery of new molecules within this Papua New Guinean Monanchora sample shows promise for further chemical investigation of this species. Chapter 2 : Kelps belonging to the genus Ecklonia from South Africa are an understudied population presenting opportunities for the discovery of new metabolites. Although many phlorotannins were isolated from this genus, sulfated phlorotannins are rare in academic literature, owing to their labile nature, with the sulfate functionality often degraded during the isolation process. The aim of this project was to develop a new method for the extraction, fractionation and purification of sulfated phlorotannins. A simple method, utilising a H2O/MeOH (1:1) mixture for extraction, an EtOAc/H2O (1:1) for fractionation and a CH3COONa/AcOH pH 4 buffer for purification was developed. Applying this method, a new sulfated phlorotannin, 1054-A, and known phlorotannins eckol and 8,8’-bieckol were isolated. This new method shows potential for the isolation of new sulfated phlorotannins from the genus Ecklonia.
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University of Galway
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Attribution-NonCommercial-NoDerivatives 4.0 International
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University of Galway Theses (Research Masters Theses)