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Etude Phytochimique Et Évaluation Des Activités Biologiques De Deux Plantes Du Genre Sedum (Crassulaceae)

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Etude Phytochimique Et Évaluation Des Activités Biologiques De Deux Plantes Du Genre Sedum (Crassulaceae) République Algérienne Démocratique et Populaire Ministère de l’enseignement supérieur et de la recherche scientifique UNIVERSITE FRERES MENTOURI CONSTANTINE FACULTE DES SCIENCES EXACTES DEPARTEMENT DE CHIMIE N0 d’ordre :……….. N0 de série :………. THESE Présentée pour obtenir le diplôme de Doctorat en Sciences en Chimie organique OPTION : Phytochimie Etude phytochimique et évaluation des activités biologiques de deux plantes du genre Sedum (Crassulaceae) Par : BENSOUICI Chawki Devant le jury composé de : Président : Prof. A. Kabouche Université frères Mentouri Constantine Rapporteur : Prof. Z. Kabouche Université frères Mentouri Constantine Examinateurs : Prof. S. Akkal Université frères Mentouri Constantine Prof. A. Zellagui Université Larbi Ben'Mhidi (OEB) Prof. L. Arrar Université Ferhat Abbes (Sétif) Prof. A. Baghiani Université Ferhat Abbes (Sétif) Année 2014-2015 Remerciements Remerciements En préambule, je souhaite rendre grâce à Dieu, le Clément et Miséricordieux de m’avoir donné la force, le courage et la patience de mener à bien ce modeste travail Je tiens à remercier sincèrement mon encadreur Pr. KABOUCHE ZAHIA, Professeur à l’Université frères Mentouri Constantine 1, de m’avoir suivi et dirigé tout au long de la réalisation de ce mémoire. Je la remercie aussi pour la confiance qu’elle a placée en moi, pour sa disponibilité permanente, pour sa patience et ses conseils. Je souhaite également remercier les membres du jury, Mr. KABOUCHE AHMED, professeur à l’Université frères Mentouri Constantine 1 qui m’a fait l’honneur d’accepter d’être président de jury. Je remercie également Mr. AKKAL SALAH, professeur à l’Université frères Mentouri Constantine 1 et Mr. ZELLAGUI AMAR, professeur à l’Université Larbi Ben'Mhidi (OEB), Mr. ARRAR LEKHMISSI, professeur à l’Université Ferhat Abbes (Sétif) et Mr. BAGHIANI ABDERRAHMANE, professeur à l’Université Ferhat Abbes (Sétif), pour l’importance qu’ils ont accordé à mon travail en acceptant d’être membres de ce jury et pour le temps qu'ils ont consacré à l'examen de ce mémoire. Enfin, mes remerciements vont également à l’équipe de l’université de Mugla, Pr. Mehmet Öztürk, Pr. Mehmet Emin Duru et à tous ceux et celles qui, de près ou de loin, m’ont apporté aide et encouragements. Qu’ils trouvent ici l’expression de ma profonde gratitude Chawki Dédicaces Je dédie ce mémoire À mes chers parents À mes frères et sœurs À tous mes amis Liste des abréviations DPPH : 1,1-Diphényl-2-PicrylHydrazyl ABTS : 2,2`-azinobis-(3-ethylbenzothiazoline-6-sulfonique) ATCC : American Type Culture Collection BHA : ButylHydroxyAnisole BHT : ButylHydroxyToluene CMI : Concentration Minimale Inhibitrice CUPRAC : Cupric Reducing Antioxidant Capacity EDTA : Ethylenediaminetetraacetic acid CI50 : Concentration Inhibitrice à 50% NCCLS : National Committee for Clinical Laboratory Standard CCM : Chromatographie sur Couche Mince CLHP : Chromatographie Liquide Haute Performance LC/MS : Chromatographie Liquide couplée à la spectrométrie de masse LC/MS/MS : Chromatographie Liquide couplée à deux spectrométries de masse COSY : Correlated Spectroscopy d : doublet dd : doublet de doublet DEPT : Distortionless Enhancement by Polarization Transfer HMBC : Heteronuclear Multiple Bonding Connectivity HSQC : Heteronuclear Single Quantum Connectivity J (Hz) : constante de couplage exprimée en Hertz RMN 1H : Résonance Magnétique Nucléaire du proton RMN 13C : Résonance Magnétique Nucléaire du carbone COSY: Correlation spectroscopy UV : Ultra-Violet λmax : longeur d’onde maximale µg : Micro-gramme ECSC : Extrait chloroformique de Sedum caeruleum EASC: Extrait acétate d’éthyle de Sedum caeruleum EBSC: Extrait butanolique de Sedum caeruleum EHSP: Extrait hexane de Sedum pubescens ECSP: Extrait chloroformique de Sedum pubescens EBSP: Extrait butanolique de Sedum pubescens Liste des tableaux No Titre Page 1 Usages et propriétés de quelques espèces du genre Sedum 12 2 Distribution des Acides phénoliques dans le genre Sedum 13 3 Distribution des Flavonoïdes dans le genre Sedum 17 4 Distribution des coumarines dans le genre Sedum 30 5 Distribution des terpenoides dans le genre Sedum 32 6 Distribution des alcaloïdes dans le genre Sedum 35 7 Distribution des mégastigmanes dans le genre Sedum 39 8 Distribution d’autres composés dans le genre Sedum 42 9 Classification des polyphénols 57 10 Structures des diffèrent flavonoïdes aglycones étudiés 61 11 Fragment ESI-MS/MS des flavones 1-6 63 12 Fragment ESI-MS/MS des flavonols 7-11 64 13 Fragment ESI-MS/MS des flavonones 12-15 65 14 Résultats de séparation par chromatographie sur colonne de gel de silice de 92 la fraction chloroformique 15 Résultats de séparation de la fraction F4 93 16 Résultats de séparation de la fraction F15 93 17 Résultats de séparation de la fraction F19 94 18 Résultats de séparation de la fraction F69 94 19 Résultats de séparation de la fraction F74 95 20 Résultats de séparation de la fraction F77 95 21 Résultats de séparation de la fraction F91 95 22 Résultats de séparation de la fraction F106 96 23 Résultats de séparation par chromatographie sur colonne de gel de silice de 96 la fraction acétate d’éthyle 24 Résultats de séparation de la fraction AC10 98 25 Résultats de séparation de la fraction AC10 98 26 Résultats de séparation de la fraction AC12 98 27 Résultats de séparation de la fraction AC12 99 28 Résultats de séparation de la fraction AC14 99 29 Résultats de séparation de la fraction AC15 99 30 Résultats de séparation de la fraction AC122 100 31 Calibration de LC/MS/MS en présence des standards 104 32 Données de la série spectrales UV du produit F60 118 1 33 Données de la RMN H du produit F60 (DMSO-d6 à 400 MHz) 119 34 Données de la série spectrale UV du produit AC10 123 1 35 Données de la RMN H du produit AC10 (CD3OD, 400 MHz) 124 36 Données de la série spectrale UV 131 37 Données de la RMN 1H du produit AC122 132 13 38 Données RMN C (400 MHz, CD3OD) du produit AC122 133 39 Déplacements chimiques en RMN1H (400MHz) et RMN 13C (100 MHz) du 142 produit F19 dans le DMSO-d6 40 Déplacements chimiques en RMN1H (400 MHz) et RMN 13C du composé 155 F75enregistré dans le DMSO-d6 13 41 Données RMN C (100 MHz, DMSO-d6) du produit F72 165 42 Composés de l’extrait butanolique identifiés par LCMSMS 199 43 Polyphénols totaux de Sedum caeruleum et Sedum pubescens. 203 44 Inhibition du radical DPPH par les extraits de S. caeruleum et S. pubescens 204 45 Activité des extraits de Sedum caeruleum sur les ions chélates 208 46 Inhibition du CUPRAC par les extraits de Sedum caeruleum 209 47 Inhibition du CUPRAC par les extraits de Sedum pubescens 210 48 Activité de blanchissement du β-carotène par les extraits de Sedum 212 caeruleum 49 Activité de blanchissement du β-carotène par les extraits de Sedum 213 pubescens 50 Activité antiradicalaire (ABTS) des extraits de Sedum pubescens 214 51 Inhibition de l’acétylcholinestérasepar les extraits de Sedum caeruleum 215 52 Inhibition de labutyrylcholinestérase par les extraits de Sedum caeruleum 217 53 Activité anti-inflammatoire in vivo de Sedum caeruleum 219 54 Résultats de l’activité antibactérienne de l’ECSC 220 Liste des figures No Titre Page 1 Photos de la plante sedum caeruleum. 11 2 Photos de la plante Sedum pubescens 11 3 Structures des acides phénoliques isolés du genre Sedum 16 4 Squelette de base des flavonoïdes 17 5 Structures des flavonoïdes isolés du genre Sedum 29 6 Structures des coumarines isolées du genre Sedum 31 7 Structures des terpenoides isolés du genre Sedum 34 8 Structures des alcaloïdes isolés du genre Sedum 39 9 Structures des mégastigmanes isolés du genre Sedum 41 10 Structures des autres composés isolés du genre Sedum 42 11 Détection des acides gras par LC/MS/MS 55 12 Classification des polyphénols 59 13 Nomenclature adoptée pour le retrocyclisation et différents clivages observés 62 dans cette étude 14 Fréquence d’utilisation des méthodes d’évaluation in vitro de l’activité 70 antioxydante 15 Principaux composés naturels (ou synthétisés) possédant des propriétés 71 antioxydantes 16 Transformation du radical DPPH• en DPPH 73 17 Formation et piégeage du radical ABTS•+ par un antioxydant donneur de H• 75 18 Réduction du complexe chromogène de Cu+2-Nc 76 19 Sites d’ions métalliques par les flavonoïdes 77 20 Mécanisme chimiques de la méthode d’Ellman’s 78 21 Schéma d’extraction de Sedum caeruleum 90 1 22 Spectre RMN H du produit F60 (CD3OD,400 MHz) 120 1 23 Spectre RMN H étalé du produit F60 (CD3OD,400 MHz) 121 1 24 Spectre RMN H du produit AC14 (CD3OD,400 MHz) 126 1 25 Spectre RMN H étalé 1 du produit AC14 (CD3OD,400 MHz) 127 1 26 Spectre RMN H étalé 2 du produit AC14 (CD3OD,400 MHz) 128 27 Identification par HPLC du produit AC14 129 1 28 Spectre RMN H du produit AC122 (CD3OD,400 MHz) 135 1 29 Spectre RMN H étalé 1 du produit AC122 (CD3OD,400 MHz) 136 1 1 30 Spectre cosy H- H du produit AC122 (CD3OD,400 MHz) 137 1 1 31 Spectre HSQC H- H du produit AC122 (CD3OD, 100 MHz) 138 32 Chromatogramme LC/MS/MS du produit AC122 139 33 Spectrométrie de masse LC/MS/MS du produit AC122 139 1 34 Spectre RMN H du produit F19 (DMSO-d6, 400 MHz) 142 1 35 Spectre RMN H étalé du produit F19 (DMSO-d6, 400 MHz) 144 36 Spectre Dept 135 du produit F19 (DMSO-d6, 100 MHz) 145 37 Spectre Dept 135 étalé du produit F19 (DMSO-d6, 100 MHz) 146 38 Spectre COSY étalé du produit F19 (DMSO-d6, 400 MHz) 147 39 Spectre COSY étalé du produit F19 (DMSO-d6, 400 MHz) 148 40 Spectre HSQC du produit F19 (DMSO-d6, 400 MHz) 149 41 Spectre HSQC du produit F19 (DMSO-d6, 400 MHz) 150 42 Spectre HMBC du produit F19 (DMSO-d6, 400 MHz) 151 43 Spectre HMBC du produit
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