Biodiversité des invertébrés marins : de l'isolement à la modélisation moléculaire de métabolites secondaires pour la découverte de nouveaux candidats médicaments

Abstract : The work described in this manuscript concerns the chemical study of four sponges from Madagascar: Monanchora unguiculata, Amphimedon sp., Aulospongus gardineri and Biemna laboutei. For the first three sponges, the study was devoted to the extraction, isolation and identification of secondary metabolites by various chromatographic (MPLC, HPLC…) and spectroscopic (UV, HRMS, 1D and 2D NMR…) techniques. Fitfteen secondary metabolites including guanidine alkaloids, bromotyrosin derivated, N-acylethanolamines and polyynes were isolated from these sponges. Eight are new molecules. The biological activities of the isolated compounds were then evaluated. Two of them, fromiamycalin (M70) and ptilomycalin F (MU7) showed a very good antimalarial activity and four of them, fromiamycalin (M70) and ptilomycalins E (MU6), G (MU8) and H (MU9) a promising cytotoxicity against KB cells. The study of the last sponge, Biemna laboutei, was performed on molecules already isolated in the LCSNSA. This work included the determination of the relative configuration of nine guanidine alkaloids by using the DP4+ probability. The relative configuration of seven molecules was confirmed. Three of them, netamines G (E8), P (E17) and R (E19) were selected for a study by molecular modeling to determine their absolute configuration by comparison of their experimental Electronic Circular Dichroism spectrum with a calculated spectrum.
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Pierre-Éric Campos. Biodiversité des invertébrés marins : de l'isolement à la modélisation moléculaire de métabolites secondaires pour la découverte de nouveaux candidats médicaments. Chimie analytique. Université de la Réunion, 2017. Français. ⟨NNT : 2017LARE0007⟩. ⟨tel-01561205⟩

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