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THESE Hanène ZATER REPUBLIQUE ALGERIENNE DEMOCRATIQUE ET POPULAIRE MINISTERE DE L’ENSEIGNEMENT SUPERIEUR ET DE LA RECHERCHE SCIENTIFIQUE UNIVERSITE FRÈRES MENTOURI CONSTANTINE FACULTE DES SCIENCES EXACTES DEPARTEMENT DE CHIMIE N° d’ordre :168/DS/2017 Série :25/CH/2017 . THESE Présentée en vue de l’obtention du diplôme de Doctorat en Sciences Spécialité : Chimie Organique Option : Phytochimie Par Hanène ZATER Constituants chimiques, propriétés cytotoxiques, antifongiques et antibactériennes de l’extrait chloroforme de Centaurea diluta Ait. subsp. algeriensis (Coss. & Dur.) Maire Devant le jury : Pr. BENAYACHE Samir Université Frères Mentouri, Constantine Président Pr. BENAYACHE Fadila Université Frères Mentouri, Constantine Directrice de thèse, Rapporteur Pr. AMEDDAH Souad Université Frères Mentouri, Constantine Examinateur Pr. LEGSEIR Belgacem Université Badji Mokhtar, Annaba Examinateur Pr. BOUDJERDA Université Mohamed Seddik Examinateur Azzeddine Benyahia, Jijel Pr. KHELILI Smail Université Mohamed Seddik Benyahia, Examinateur Jijel 15/07/ 2017 ۞بِ ْس ِم هَّللاِ ال هر ْح َم ِن ال هر ِحي ِم ۞ ۞ ُس ْب َحانَ َك ََل ِع ْل َم لَنَا إِ هَل َما َعله ْمتَنَا ۖ إِنه َك أَ ْن َت ا ْل َعلِي ُم ا ْل َح ِكي ُم ۞ ﴿ ص َد َق آهلل العل ٌي آلعظ ْيم﴾ Dédicaces ♥A L’âme de ma grande -mère & mon grand-père &Ami Djamel… ♥A mes chers parents Akila & Abderrazek … ♥A mes chères sœurs : Amel, Ibtissem, Schehra, Lamia, Faiza Mouna ♥ A mon frère Ahmed Souheil. ♥A mes neveux. ♥A mes oncles & tantes… ♥ A tous mes amis & collègues !!! ♥ A tous ceux qui ont contribué un jour à mon éducation !!! Je dédie ce modeste travail. Hanène Remerciements En préambule, je souhaite rendre grâce au bon Dieu « ALLAH », le Clément et Miséricordieux de m’avoir donné la force, le courage et la patience de mener à bien ce modeste travail. Au terme de ce travail de recherche qui a été réalisé à la Faculté de Pharmacie de l’Université Libre de Bruxelles (ULB), je souhaiterais adresser mes remerciements aux personnes et institutions qui ont contribué à son accomplissement. Je remercie vivement le Ministère de l’Enseignement Supérieur et de la Recherche Scientifique Algérien qui m’a fait bénéficier d’une bourse de type PNE. Je tiens à remercier sincèrement ma directrice de thèse Mme Fadila BENAYACHE, Professeur à l’Université des Frères Mentouri Constantine 1, de m’avoir suivie et dirigée tout au long de la réalisation de cette thèse et pour toute l'aide, la patience, la disponibilité, les conseils précieux, les critiques constructives et le soutien humain, à la fois dans le développement de cette thèse comme dans tous les processus administratifs. Recevez ici mon profond attachement, ma gratitude et ma sincère reconnaissance & Merci pour tout… Je remercie tout particulièrement et j'exprime toute ma gratitude à mon co-directeur de thèse Mr.Pierre DUEZ Professeur à l’Université de Mons (UMONS) actuellement, pour m’avoir accueillie dans son laboratoire et pour avoir initié et encadré ce travail coté biologique, pour m’avoir témoigné de sa confiance en mettant tout en œuvre pour que ce travail soit réalisé dans son laboratoire. J’ai eu le temps d’apprécier son esprit scientifique. Je remercie également Mme Caroline STEVIGNY, Professeur à l'Université Libre de Bruxelles (ULB) pour la générosité humaine qui a accompagné sa participation à ce travail, pour m’avoir offert tant de possibilités. Je la remercie pour tout le soutien, les encouragements, la sympathie, le suivi journalier, l'énergie, le dévouement et les précieux conseils scientifiques en matière de botanique. ii J’exprime toute ma reconnaissance à Mr. Samir BENAYACHE, Professeur à l’Université des Frères Mentouri Constantine 1, pour sa disponibilité, ses conseils précieux et pour le grand honneur qu’il me fait en acceptant de présider le jury de soutenance. Toute ma gratitude va aussi à Mme Joëlle HUET, Docteur du Laboratoire des Biopolymères et des Nanomatériaux Supramoléculaires de l’ULB qui m’a enseigné tout ce que je sais au sujet des tests antifongiques. Merci pour votre aide et pour votre sympathie. Merci pour tout ce que vous m’avez appris, pour votre patience, votre dévouement, votre disponibilité et pour l'amitié que vous m’avez témoignée tout au long de l'année. Ma gratitude va également à tous les membres du jury Mme Souad AMEDDAH Professeur de l'Université des Frères Mentouri Constantine 1, Mr. Belgacem LEGSEIR Professeur de l'Université Badji Mokhtar Annaba, Mr. Azzeddine BOUDJERDA Professeur de l'Université l'Université Mohamed Seddik Ben Yahia, Jijel), Mr. Smaïn KHELILI Professeur de l'Université Mohamed Seddik Ben Yahia, Jijel) qui, malgré leurs multiples occupations, ont accepté d’examiner cette thèse et juger ce travail. J’ai pu bénéficier pour réaliser ce travail de l’accueil et de l’aide de certains laboratoires que je remercie de tout cœur : Haut-Commissariat au Développement de la Steppe « HCDS » & Conservation des Forêts Djelfa, Algérie (la récolte de la plante étudiée) ; Laboratoire Biodiversité et Ressources Phytogénétiques, Faculté des Sciences Biologiques Université Ferhat Abbes Sétif, Campus El-Baz, Setif, Algérie (identification de l’espèce végétale étudiée : Pr. Mohamed KAABECHE) ; Herbarium du jardin Botanique de Meise, Bruxelles , Belgique (authentification & dépôt de l’herbier : Mme Bibiche Mato) ;Laboratoire de Cancérologie et Toxicologie de l’ULB (tests cytotoxiques : Pr. Véronique MATHIEU et Thierry GRAS), Unité de Microbiologie Pharmaceutique et Hygiène de l’ULB (tests antibactériens directs & indirects : Pr. Véronique FONTAINE et Dr. J. NGEZAHAYO) ; CHU Charleroi (tests antimicrobiens : G. LARSON et D. FAMMEREE) ; Centre Wallon de Biologie Industrielle, Bio-Industrie Unité Gembloux Agro-BioTech ; Université de Liège, de Gembloux (tests antifongiques : Pr. Marc ONGENA et Dr. J. HUET; Service du Laboratoire de RMN de l’ULB (enregistrement de spectres de RMN : Pr. M. LUHMER, Dr. L. POTIER), Unité de recherche: Valorisation des Ressources Naturelles, Molécules Bioactives et Analyses iii Physicochimiques et Biologiques (VARENBIOMOL), Constantine, Algérie (enregistrement de spectres UV) ; Laboratoire de Chimie Pharmaceutique Organique de l’ULB (enregistrement des spectres de masse : Dr. C. DELPORTE) ; Institut Meurice – Service de Chimie Organique Haute Ecole Lucia de Brouckère Avenue Emile Gryzon, Bruxelles (Mesure des pouvoirs rotatoires : Dr. E. GICQUEL et J. VANCAUTENBERG). Je voudrais exprimer ma gratitude au Pr. Ali CHOKRI recteur de l'Université de Djelfa, à Mr. Abdallah TOUNSI Vice-consul d’Algérie à Bruxelles pour l’aide précieuse dans la procédure de la prolongation de mon séjour. Mes remerciements vont à toute l’équipe du Laboratoire de Pharmacognosie, Bromatologie et Nutrition Humaine: à Marie FAES et Olivier VAILLANT pour votre disponibilité et le matériel que vous avez mis à ma disposition. A vous mes chers collègues chercheurs et stagiaires (Laurent, Jérémie, Philippe, Léocadie, Carole, Valérian, Sofia, Jacob, Naïma, Fatiha, Sihem, Jallel, Ahmed, Amel, Bakari, Albert). Merci pour vos encouragements et, tout particulièrement, pour la bonne ambiance que votre présence a créée au laboratoire. J’ai autour de moi tout un réseau d’amis et de proches qui, de diverses manières, m’ont aidé à aller jusqu’au bout de ce travail. Qu’ils trouvent ici l’expression de ma profonde gratitude. Je cite en particulier : Hafida, Houssem, Sandra, Schehrazed, Eva, Sabrina, Ouahiba, Sana, Lamia, Sarah, Rebiha, Salima, & Fatima Zohra… A tous ceux, que je n´ai pas nommé, et qui de près ou de loin ont contribué à l´élaboration de ce travail. Je remercie chaleureusement toute ma famille, arrières grand-mères, grands-parents, oncles, tantes et tous mes cousins, de tout cœur pour leur soutien. iv Liste des abréviations & acronymes - AB : Antibiotique - AcOH : acide acétique - ADN : Acide desoxyribonucléique - A431 : lignée cellulaire humaine modèle (carcinome épidermoïde) - A549 : carcinome humain du poumon non à petites cellules - AcOEt : acétate d’éthyle - AlCl3 : chlorure d’aluminium - Alg. Mar. : Algérien Marocain - ans : anthères - ARN : Acide ribonucléique - ATCC : American Type Culture Collection - ATM : (Ataxia Telangiectasia Mutated) est la protéine mutée dans le syndrome 20 - []D : Pouvoir rotatoire - B16-F10 : lignée cellulaire de cancer murin - BMR : bactérie multirésistante aux antibiotiques - BuOH : n- butanol - C: capitule. - CH2Cl2: Dichloromethane - CHCl3: Chloroforme - CH3COCH3: Acétone - CDCl3 : Chloroforme deutétré - CD3OD : Méthanol deutéré - CoA : coenzyme A - DMSO : diméthylsulfoxyde - DMSO-d6 : diméthylsulfoxyde deutéré - CC : chromatographie sur colonne - CCC: très commun. - CCM : chromatographie sur couche mince - CO2 : dioxyde de carbone - CFU : Colonies Forming Units v - CMB: Concentration Minimale Bactéricide - CMI: Concentration Minimale Inhibitrice - CFU : Colonies Forming Units - CMB : Concentration Minimale Bactéricide - CMI : Concentration Minimale Inhibitrice - DMSO : Diméthylsulfoxyde - 13C : carbone 13 - CDC25 : Cycle cellulaire - COSY: Correlated Spectroscopy - CP : chromatographie sur papier ; - cp : capitule - d : doublet - dd : doublet de doublet - DEPT: Distortionless Enhancement by Polarization Transfert - DO : densité optique - DSMZ: Deutsche Sammlung von Mikroorganismen und Zellkulturen - δ (ppm) : Déplacement chimique en partie par million - E : Est - ECACC: European Collection of Authenticated Cell Cultures - E. coli: Escherichia coli - EDTA: Ethylene-Diamine-Tetra-Acetic acid (Acide Éthylène Diamine Tétraacétique ; C10H16N2O8) - ESI : Ionisation par l'électronébulisation
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