Sphingolipides, triterpènoïdes et autres métabolites secondaires des variétés sauvage et cultivée de l'espèceTriumfetta Cordifolia A. Rich (Tiliaceae) : transformations chimiques et évaluation des propriétés biologiques de quelques composés isolés

Abstract : From decade, plants are used in traditional healer to treat many diseases. This could be explained by microorganism pharmaceutical drug resistance. Beside, the poverty limits also access to modern treatment. That is why the present work deals with extraction, isolation, structural elucidation, chemical transformation and biological evaluation of secondary metabolites isolated from the wild and cultivated species of Triumfetta cordifolia A Rich (Tiliaceae). From the organic extract of twigs and leaves of wild T. cordifolia, four new compounds were characterized (two ceramides and two triterpens) by successive chromatography methods and identified as (2R, 6Z)-2-hydroxy-N-[(2S,3S,4R)-1,2,4-trihydroxyhexacosan-2-yl]heptadec-6enamide, {(2R)-N-(1S,2R,3E,6Z,9Z,12Z,15Z)-1-[(beta-D-glucopyranosyloxy)methyl]-2-hydroxy heneicosa-3,6,9,12,15-pentaen-1-yl}-2-hydroxytetradecanamide, 3-O-propanoyl-29-O-triacontanoylstigmasta-5,22-diene-3beta,29-diol et l'acide 2alpha,3beta,19alpha-trimethoxyurs-12-ene-24,28-dioique-24-[(2alpha,3beta)-24,28-bis(beta-D-glucopyranosyloxy)-2-hydroxy-24,28-dioxours-12-en-3-yl] ester acid..These compounds were obtained together with eleven known compounds identified as heptadecanoic acid, beta-sitostérol glucopyranoside, friedelin, lupeol, betulin, oleanolic acid, maslinic acid, corosolic acid, the mixture of stigmasterol and beta sitosterol, heneicosanoic acid and trans-tiliroside. From the organic extract of twigs and leaves of cultivated species, ten products were isolated ; three among of them have not yet been identified, four of them were already obtained from the wild species and the rest were identified as Tormentic acid, beta-carotene and 24-hydroxytormentic acid. The structures of these compounds were determined on the basis of NMR data(1H, 13C, two dimensional NMR analyses), mass spectrometry structure of new compounds were confirmed by chemical transformations while those of known compounds were confirmed by comparison of their physical and spectral data with those reported in the literature and with authentic samples for some of them. Stigmasterol was subjected to different oxidation reactions. The cytotoxic activities of the products and some isolated compounds against human fribosarcoma cell line HT1080 were evaluated. The flow cytometry was used to carry out this assay and some drugs showed good cytotoxic activities although inducing at the same time the apoptopic and necrotic dead of cells. The antioxidant properties of some fractions and compounds were also evaluated by FRAP method. Trans-tiliroside and its fraction showed good antioxidant activity. This work reveals the preventive and curative character of both eatable plants since these species could be used against oxidative stress. Other biological studies could be deepened to highlight the anticancer property of some isolated compounds
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Louis Pergaud Sandjo. Sphingolipides, triterpènoïdes et autres métabolites secondaires des variétés sauvage et cultivée de l'espèceTriumfetta Cordifolia A. Rich (Tiliaceae) : transformations chimiques et évaluation des propriétés biologiques de quelques composés isolés. Autre. Université Paul Verlaine - Metz, 2010. Français. ⟨NNT : 2010METZ006S⟩. ⟨tel-01752741⟩

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