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Table Des Matières الجمهورية الجزائرية الديمقراطية الشعبية RÉPUBLIQUE ALGÉRIENNE DÉMOCRATIQUE ET POPULAIRE وزارة التعليم العالي والبحث العلمي MINISTÈRE DE L’ENSEIGNEMENT SUPÉRIEUR ET DE LA RECHERCHE SCIENTIFIQUE جامعة اﻻخوة منتوري قسنطينة Université des Frères Mentouri Constantine كلية علوم الطبيعة والحياة Faculté des Sciences de la Nature et de la Vie قسم الكيمياء الحيوية و البيولوجيا الخلوية و الجزئية Département de Biochimie et Biologie Moléculaire et Cellulaire Mémoire présenté en vue de l’obtention du Diplôme de Master 2 Domaine : Sciences de la Nature et de la Vie Filière : Sciences Biologiques Spécialité : Biochimie de la nutrition Intitulé Isolement et Caractérisation Structurale de Curcuminoides d’Origine Naturelle Présenté et soutenu par :BOUFEKER Sanaa Le : 28/06/2018 AGGOUNE Dallel Zouleikha Jury d’évaluation : Président du jury : Mr. Nouadri Tahar (MCA- UFM Constantine1). Rapporteur : Mme MOUAS T.Nardjes (MCA - UFM Constantine1). Examinateur : Mme.Dallouche Aziza (MCA- UFM Constantine1). Année universitaire 2017- 2018 Remerciements Nous tenons tout d’abord à remercier DIEU tout puissant, qui en son nom et avec sa protection, nous avons réussi à réaliser ce travail. Nous souhaitons remercier Madame Mouas Toma Nardjes Maitre de conférences à l’UFM Constantine1, pour nous avoir accueillies au sein du département de Biochimie de l’Université des Frères Mentouri pour effectuer ce travail de recherche et le valoriser au mieux. Nous remercions également le président du jury Mr Nouadri Tahar Maitre de conférences classe A à l’Université des Fréres Mentouri Constntine, et Mme Dalloche Aziza Maitre de conférences classe A à UMC , de nous faire l’honneur de juger ce travail. Un merci bien particulier est adressé à Monsieur Khlelifi. D, professeur à l’université Frères Mentouri, Constantine, pour nous avoir accueillis dans son laboratoire GBBV. Sans oublié Monsieur Eric Manoury directeur de recherche au LCC, Toulouse, France d’avoir eu l’amabilité d’effectuer nos analyses RMN dans son service. Nous adressons nos sincères remerciements à tous les professeurs, intervenants et toutes les personnes qui par leurs paroles, leurs écrits, leurs conseils et leurs critiques ont guidé nos réflexions jusqu’à l’obtention du diplôme de master. Nous finissons par remercier nos chers parents pour l’aide qu’ils nous ont apporté tout au long de notre vie. Boufeker Sanaa Aggoune Dallel Zouleikha DEDICACE Je remercie ALLAH le clément pour m’avoir aidé durant toute ma vie. Je dédie ce modeste travail: A mes parents .Aucun hommage ne pourrait être à la hauteur de l’amour Dont ils ne cessent de me combler. Que dieu leur procure bonne santé et longue vie. A celui que j’aime beaucoup et qui m’a soutenue tout au long de ce projet : mon mari ADEL, et bien sur A mes enfants KOUSSAI, MAHITEB, TIN-HINANE et AMIR, sans oublier mes frères et ma chère sœur que j’aime. A toute ma famille, et mes amis, A mon binôme SANAA et toute la famille BOUFEKER. Et à tous ceux qui ont contribué de près ou de loin pour que ce projet soit possible, je vous dis merci. Dallel DEDICACE Je dédie ce travail à : Mes chers parents pour leur amour inestimable,leur confiance, leur soutien, leurs sacrifices et toutes les valeurs qu'ils ont su m'inculquer. Mon cher mari, pour sa précieuse compréhension Mes plus belles filles pour leur présence dans ma vie Mes sœurs et mes belles sœurs pour leur tendresse, leur complicité et leur présence, ainsi qu’à mon frère Ma belle-mère qui ma soutenue tout au long de ce travail j'espère que la vie vous réserve le meilleur. Au reste de la famille BOUFEKER , Pour leur soutient jusqu'à la fin de ce travail, ainsi qu'à Tous mes collègues de travail pour leur aide et encouragements. Tous mes chers amis Pour leur soutien et leur amitié Chaleureuse qui nous a réuni dans ce travail. Mon cher binôme Dallel qui a partagé avec moi les moments difficiles de ce travail. Sanaa Table des matières Table des matières Tables des matières…………………………………………………………I Abréviations………………………………………………………………...II Liste des figures……………………………………………………………III Liste des tableaux………………………………………………………….IV Introduction générale………………………………………………………01 Partie I : Aspects Bibliographiques CHPITRE I : L’espèceCurcuma longa.L I.Historique de la plante …………………………………………………………………….03 I. 2. Terminologie…………………………………………………………………………...03 I.3. Systématiques…………………………………………………………………………...05 I.4.Répartition géographique………………………………………………………………..06 I.5.Description botanique de la plante……………………………………………………....06 I.5.1.Caractères morphologiques……………………………………………………………06 I.5.2.Caractères microscopiques……………………………………………………….……08 I.6.Vertus………………………………………………………………………………...….08 I.7.Composition chimique…………………………………………………………………..11 I.8.Activités biologique de l’extrait brut du Curcuma Longa.L……………………..….…..13 I.8.1. Activité antioxydante…………………………………………………………………13 I.8.2. Activité anti-inflammatoire …………………………………………………………..13 I.8.3. Activité antimicrobienne……………………………………………………………...14 CHAPITRE II : Les Curcuminoides II.1.Propriétés physicochimiques …………………………………………………………..15 II.1.1.Structure chimique…………………………………………………………………...15 II .1.2.Solubilité…………………………………………………………………………….16 II .1.3.Biodisponibilité……………………………………………………………………...17 II.1.4.Les analogues structuraux de la Curcumine………………………………….....…18 II.1.4.1. Les analogues naturels de la curcumine ……………………………..................18 II.1.4.2. Les analogues synthétiques de la curcumine……………………………………....20 II.1.4.3. Les relations structure-activité (RSA) ……………………………………………22 II.2.Activités biologiques…………………………………………………………………...23 II.2.1.Activité antioxydante………………………………………………………………...23 II.2.2.Activité anti-inflammatoire…………………………………………………………..23 CHAPITRE III : Techniques D’analyses Introduction…………………………………………………………………………………25 III.1.Extraction……………………………………………………………………………...25 III .1.1.Extraction par solvant organique……………………………………………….…...26 III .1.2. Extraction par ultrason……………………………………………………………...26 III .1.3. Extraction par absorbance…………………………………………………………..26 III .1.4. Extraction par CO2 supercritique…………………………………………………..27 Table des matières III.2.Chromatographie………………………………………………………………………27 III.2.1.Bref Historique………………………………………………………………………27 III.2.2.Définition…………………………………………………………………………….28 III.2.3.Classification………………………………………………………………………...28 III.2.4.Types de chromatographie…………………………………………………………...29 III.2.4.1.Chromatographie sur colonne……………………………………………………...29 III.2.4.2.Chromatographie en couche mince………………………………………………..30 III.3.Spectroscopie de Résonance Magnétique Nucléaire…………………………………..31 III.3.1. Différents Type de RMN…………………………………………………………....32 III.3.1.1.RMN 1H…………………………………………………………………………....32 III.3.1.2.RMN 13C……………………………………………………………………….…..33 III.3.1.3.Spectroscopie Corrélée Homonucléaire, COSY…………………………………...33 III.3.1.4. Spectroscopie d'amplification nucléaire Overhauser, NOESY…………………..34 III.4.Domaine d’application…………………………………………………………………34 III.4.1.Applications RMN en biologie végétale………………………………………….….34 III.4.2.Applications RMN en toxicologie……………………………………………….…..34 III.4.3.Applications RMN en Chimie Organique…………………………………………...35 Partie II : Aspects Expérimentaux CHPITRE I : Matériel et Méthodes I.1.Matériel…………………………………………………………………………………36 I.1.1.Matériels Végétal……………………………………………………………………...36 I.1.2.Matériel et produits de laboratoire……………………………………………………36 I.2.Méthodes………………………………………………………………………………..37 I.2.1.Enquête ethnobotanique……………………………………………………………….37 I.2.2.Séchage………………………………………………………………………………..38 I.2.3.Extraction……………………………………………………………………………...38 I.2.4.Séparation……………………………………………………………………………...40 I.2.4.1.Chromatographie sur colonne…………………………………………………….....40 I.2.4.2.Chromatographie liquide sur couche mince………………………………………....43 I.2.5.Caractérisation par RMN1H……………………………………………………...……46 CHAPITRE II: Résultats et Discussion II.1.Résultats………………………………………………………………………………...48 II.1.1.Enquête ethnobotanique …………...…………………………………………….…...48 II.1.2.Séchage……………………………………………………………………………….51 II.1.3.Rendement de l’extraction…………….…………………………………………...…52 II.1.4.Séparation et identification…………………………………………………………...53 II.1.4.1.Chromatographie sur colonne……………………………………………………....53 II.1.4.2.Chromatographie liquide sur couche mince………………………………………...55 II.1.6.Caractérisation structurale par RMN1H………………………………………..……..59 II.2.Discussion…………..……………………………………………………………..…...63 II.2.1.Enquête ethnobotanique………………………………………………………………63 II.2.2.Séchage……………………………………………………………………………….64 II.2.3.Rendementde l’extraction...……………………………………………………..……64 II.2.4.Séparation et isolement de la curcumine……………………………………………..66 II.2.4.1.Chromatographie sur colonne………………………………………………………66 II.2.5.Caractérisation structuralepar RMN1H…..………………………………………….68 Table des matières Conclusion.……………….…..…………………………………….………70 Références………………..…………………………………………..………73 Annexes……………………………………………………………………….79 Résumés Liste des figures Figure Titre Page 1 Classification phylogénétique du végétal Curcuma. 05 2 Aspect des rhizomes de Curcuma Longa.L. 08 3 Les composés de Curcuma longa peuvent influencer positivement 11 plusieurs pathologies. 4 Structure chimique des différentscurcuminoides. 16 5 Les analogues naturels de la curcumine. 18 6 Les analogues synthétiques de la curcumine. 22 7 Structures du curcumol et des curcuminoïdes retrouvées dans le 23 Curcuma sp. 8 Développement historique de la chromatographie liquide. 28 9 Dessin d'une colonne de chromatographie liquide. 30 10 Exemple d’utilisation d’une CCM. 31 11 Diagramme schématique détaillant les principaux composants d'un 32 spectromètre à résonance
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