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Sce HABA HAMADA.Pdf REPUBLIQUE ALGERIENNE DEMOCRATIQUE ET POPULAIRE MINISTERE DE L’ENSEIGNEMENT SUPERIEUR ET DE LA RECHERCHE SCIENTIFIQUE UNIVERSITE EL HADJ LAKHDAR BATNA FACULTE DES SCIENCES DEPARTEMENT DE CHIMIE THESE DE DOCTORAT EN SCIENCES SPECIALITE : CHIMIE Présentée par HABA HAMADA Thème Etude phytochimique de deux Euphorbiaceae sahariennes : Euphorbia guyoniana Boiss. et Reut. et Euphorbia retusa Forsk. Soutenue publiquement le 03 juillet 2008 JURY Ammar DIBI Professeur Université de Batna Président Mohammed BENKHALED Professeur Université de Batna Rapporteur Fadila BENAYACHE Professeur Université de Constantine Examinatrice Samir BENAYACHE Professeur Université de Constantine Examinateur Kaddour LAAMARA Professeur Centre Universitaire de Oum Examinateur El Bouaghi Abdelhamid BENKOUIDER Maître de Conférences Université de Batna Examinateur Remerciements Cette thèse de Doctorat en chimie est le résultat d’un travail de collaboration entre les universités de Batna Algérie et Reims France. La 1ère partie de cette recherche est réalisée au laboratoire de chimie et chimie de l’environnement (LCCE) de la faculté des Sciences université de Batna, sous la direction du professeur BENKHALED Mohammed, je tiens à lui exprimer toute ma reconnaissance et profonde gratitude pour m’avoir accueilli au sein de l’unité de phytochimie du laboratoire de chimie et chimie de l’environnement (LCCE) et de m’avoir permis de préparer mon doctorat dans les meilleures conditions. Je tiens à le remercier tout particulièrement pour tous ses efforts et ses encouragements et pour le soutien qu’il m’a témoigné tout au long de cette étude placée sous sa direction. J’ai eu la chance et le plaisir d’effectuer la 2ème partie de ce travail de recherche dans le laboratoire de pharmacognosie de la faculté de pharmacie de Reims France dirigé par le professeur Janos SAPI, sous la direction du professeur Catherine LAVAUD. Je tiens à lui exprimer mes sincères remerciements pour m’avoir accueilli au sein du laboratoire de pharmacognosie, pour m’avoir fait confiance et m’avoir permis de réaliser ce travail dans de meilleures conditions tout en me laissant une grande liberté. Pour son aide et pour les discussions enrichissantes et fructueuses entretenues durant ma présence dans son laboratoire, qu’elle soit assurée de ma profonde gratitude. Mes vifs remerciements vont également à Monsieur le professeur DIBI Ammar de l’université de Batna pour l’honneur qu’il nous a fait en acceptant de présider le jury de ma soutenance de thèse de doctorat. J’aimerais également remercier vivement Madame le professeur BENAYACHE Fadila de l’université de Constantine, Monsieur le professeur BENAYACHE Samir de l’université de l’université de Constantine, Monsieur le professeur LAAMARA Kaddour du Centre universitaire de Oum El bouaghi et Monsieur BENKOUIDER Abdelhamid, maître de conférences à l’université de Batna pour avoir accepté de faire partie de mon jury de thèse. Je tiens particulièrement à exprimer ma reconnaissance à Monsieur le professeur BENDAIKHA Tahar, directeur du laboratoire de chimie et chimie de l’environnement LCCE de l’université de Batna et doyen de la faculté des Sciences pour son soutien et ses encouragements. J’exprime mes sincères remerciements à Georges Massiot, Laurence Marcourt, Christophe Long du centre de recherche sur les substances naturelles de Pierre Fabre de Toulouse France, pour leur aide et disponibilité en me permettant la réalisation des spectres RMN et Masse. Je remercie également tous les membres du laboratoire de pharmacognosie de Reims pour leur soutien et les facilités accordées pour la réalisation de ce travail : Madame le professeur Monique ZECHES, le Dr. Abdulmagid alabdul Magid, le Dr. Laurence Voutquenne-Nazabadioko, le Dr. Christophe BLIARD, le Dr. Jean-Marc NUZILLARD, le Dr. Catherine CARON, Bernard RICHARD, Mariejoe JACQUIER, Agathe MARTINEZ, Jean PATRICK,…... J’exprime également mes remerciements à mes collègues de l’unité de phytochimie du laboratoire de chimie et chimie de l’environnement LCCE pour leur amitié et gentillesse: Mohammed, Hassina, Fatima, Lynda, Rachid, Souad, Hakim, Sonya, Fatiha, Rahima, …… Je tiens à remercier le ministère de l’enseignement supérieur et de la recherche scientifique Algérien pour la bourse qui m’a été accordée dans le cadre du PNE 2006/2007 afin de finaliser ma thèse. Dédicace Cette thèse est dédiée à : A mes chers parents qui m’ont encouragé à être ce que je suis, avec tant d’amour. A ma chère femme Ikram, qui par sa compréhension, sa tendresse et ses encouragements, a soutenu sans cesse mes efforts durant la réalisation de ce travail. A mes chers enfants : Ines, Massil et Sylia pour leur amour A mes chers frères et Sœurs ainsi que ma famille pour leurs encouragements A tous mes amis et collègues. Abréviations AcOEt : acétate d’éthyle MeOH : méthanol ACN : acetonitrile CHCl3 : chloroforme CH2Cl2 : dichlorométhane EtOH : éthanol KOH : hydroxyde de potassium Na2SO4 : sulfate de sodium CDCl3 : chloroforme deutérié CD3OD : méthanol deutéré DMSO-d6 : diméthylsulfoxyde deutérié TFA : acide trifluoroacétique CCM : chromatographie sur couche mince CC : chromatographie sur colonne ouverte de silice CPP : chromatographie sur plaque préparative GC-MS : chromatographie gazeuse coupleé à la spectrométrie de masse VLC : chromatographie liquide sous vide CLHP : chromatographie liquide haute performance SiO2 : gel de silice normale C18 : Silice greffée ax : axial éq : équatorial quint : quintuplet sept : septuplet q : quadruplet qd : quadruplet de doublet d : doublet dd : doublet de doublet ddd : doublet de doublet de doublet dt : doublet de triplet dtl : doublet de triplet large t : triplet td : triplet de doublet tdd : triplet de doublet de doublet ddl : doublet de doublet large dl : doublet large s : singulet sl : singulet large m : multiplet dm : doublet de multiplet l : large Cq : carbone quaternaire RMN 1H : résonance magnétique nucléaire du proton RMN 13C : résonance magnétique nucléaire du carbone 13 COSY H-H : correlated spectroscopy HSQC : heteronuclear single quantum connectivity HMBC : heteronuclear multiple bonding connectivity NOESY : Nuclear overhauser effect spectroscopy NOE : nuclear Overhauser effect RMN : résonance magnétique nucléaire δ : déplacement chimique exprimé en ppm W1/2 : largeur spectrale à mi-hauteur J (Hz) : constante de couplage exprimée en Hz SM : spectrométrie de masse EI : impacte électronique ESI : spectrométrie de masse par electrospray FAB : bombardement d’atomes rapides HR : haute résolution uma : unité de masse atomique m/z : masse/charge d’un ion Na : sodium K : potassium IR : infra-rouge UV : ultra-violet Rdt. : rendement ATP : adénosine triphosphate CDP : copalyl diphosphate DMAPP : diméthylallyl diphosphate FDP : farnésyl diphosphate GDP : géranyl diphosphate GGDP : géranylgéranyk diphosphate GGPP : géranylgéranyl pyrophosphate IPP : isopentényl diphosphate MVA : mévalonate NADPH : nicotinamide adénine dinucléotide phosphate VAM : voie de l’acide mévalonique Réf. : référence Lit. : littérature SOMMAIRE Introduction ………………………………………….……..…………………………………….1 Chapitre I- Rappels bibliographiques……………………………...…………………….…4 I-1- Position systématique de la famille des Euphorbiaceae…………...………….………………....5 I-2- Caractères morphologiques généraux de la famille Euphorbiaceae…………………………..…6 I-3- Utilisation en médecine traditionnelle ………………………………………………………..…7 I-4- Autres usages ………………………………………………………………………………..…..8 I-5- Présentation du genre Euphorbia ……………………………………………………….………9 I-6- Métabolites isolés du genre Euphorbia ………………………………………………………..10 I-6-1- Diterpénoïdes………………………………………………………………………….……..10 I-6-2- Triterpénoïdes………………………………………………………………………………..24 Chapitre II- Etude des terpénoïdes……………………..………………………………….37 II-1- Généralités……………………………………………………………………………………..38 II-2- Biosynthèse des terpènes………………………………………………………….…………...38 II-3- Diterpènes …………………………………………………………………………………….41 II-3-1- Introduction …………………………………………………………………………………41 II-3-2- Biosynthèse des diterpènes………………………………………………………………….41 II-3-3- Propriétés biologiques et emplois des drogues à diterpènes ………………………………..46 II-4-Triterpènes……………………………………………………………………………………...47 II-4-1- Introduction……………………………………………………………………………….....47 II-4-2- Biosynthèse des triterpènes……………………………………………………………….....47 II-4-3- Intérêts des triterpènes ……………………………………………………………………...52 Chapitre III- Etude phytochimique de l’espèce Euphorbia guyoniana Boiss and Reut. ..……………………………………………………………………………………………..53 III-1- Rappels botaniques …………………………………………………………………………..54 III-2- Toxicité ………………………………………………………………………………………55 III-3- Utilisation en médecine traditionnelle ……………………………………………………….55 III-4-Travaux antérieurs sur l’espèce……………………………………………………………….55 III-5- Chimie extractive …………………………………………………………………………….56 III-5-1- Extraction …………………………………………………………………………………56 III-5-2- Purification ……………………………………………………………………………..….57 III-6- Caractérisation des produits obtenus ………………………………………………………...59 III-6-1- Produits nouveaux …………………………………………………………………………59 III-6-2- Produits connus ……………………………………………………………………………59 III-6-3- Elucidation structurale du composé 1………………………................................................63 III-6-4- Elucidation structurale du composé 2………………………................................................72 III-6-5- Elucidation structurale du composé 3………………………................................................81 III-6-6- Elucidation structurale du composé 4………………………................................................86 III-6-7- Elucidation structurale du composé 5………………………................................................89
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