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Études chimiques et biologiques d’Aframomum sceptrum (Zingiberaceae) et de la curcumine

Abstract : During our research for fighting human African trypanosomiasis (sleeping sickness), two approaches were employed; firstly the traditional use of plants, secondly the synthesis of original derivatives of curcumin.In the first part, a bioguided fractionation of a methanolic extract of the rhizomes of Aframomum sceptrum K. Schum (Zingiberaceae) allowed the isolation of five compounds, including new labdanes, named sceptrumlabdalactone A and sceptrumlabdalactone B successively. Sceptrumlabdalactone B was reasonably active against T. brucei brucei, and strongly active against L. donovani, with IC50 close to that of pentamidine.The essential oil from the rhizomes of the species might also contribute to its biological activity. It was obtained by hydrodistillation and analyzed by GC–MS. Its major constituents were β-pinene, caryophyllene oxide and cyperene. It exhibited strong bactericidal activity against Gram-positive bacteria. It only showed moderate bacteriostatic activity against Gram-negative bacteria. Remarkable activities against T. b. brucei and Trichomonas vaginalis were also observed.The second part is devoted to curcumin. This diarylheptanoid, is common in several Curcuma spp.Structural modifications and preparation of nanoparticles of curcumin were carried out to increase its activities and/or overcome the problem of the low bioavailability of this compound.Original analogs, e.g. prenylated curcumins were prepared. Several biological activities (antiparasitic, anti-inflammation, Inhibition of β–amyloid aggregation, etc) were evaluated in vitro.Similarly, the oxidative dearomatization of curcumin and its analogues allowed the access to novel original compounds.Finally, the coupling of curcumin and squalene was achieved. The resulting molecules were able to form spherical nanoassemblies that may overcome bioavailability issues. Antiparasitic, antibacterial, and cytotoxic activities were also evaluated. The in vitro leishmanicidal activity seems promising.
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Zakaria Cheikh Ali. Études chimiques et biologiques d’Aframomum sceptrum (Zingiberaceae) et de la curcumine. Autre. Université Paris Sud - Paris XI, 2012. Français. ⟨NNT : 2012PA114814⟩. ⟨tel-00812878⟩



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