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Mentha Aquatica, Stachys Guyoniana Et Thymus Dreatensis (LAMIACEAE)

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Mentha Aquatica, Stachys Guyoniana Et Thymus Dreatensis (LAMIACEAE) REPUBLIQUE ALGERIENNE DEMOCRATIQUE ET POPULAIRE MINISTERE DE L’ENSEIGNEMENT SUPERIEUR ET DE LA RECHERCHE SCIENTIFIQUE UNIVERSITE DES FRERES MENTOURI-CONSTANTINE FACULTE DES SCIENCES EXACTES DEPARTEMENT DE CHIMIE N° d’ordre : Série : THESE: Présentée en vue de l’obtention du diplôme du Doctorat en Sciences Spécialité: Chimie organique INTITULÉ: ETUDE PHYTOCHIMIQUE ET ÉVALUATION DES ACTIVITÉS BIOLOGIQUES DES ESPÈCES : Mentha aquatica, Stachys guyoniana et Thymus dreatensis (LAMIACEAE) Par FERHAT MARIA Devant le jury : Pr. Ahmed KABOUCHE (U. des frères Mentouri-Constantine) Président Pr. Zahia KABOUCHE (U. des frères Mentouri-Constantine) Rapporteur Pr. Salah AKKAL (U. des frères Mentouri-Constantine) Examinateur Pr. Amar ZELLAGUI (U. Larbi Ben M'hidi - Oum El-Bouaghi) Examinateur Pr Abdelmalik BELKHIRI (U. Constantine 3) Examinateur Dr. Nadji BOULEBDA (U. Mohamed Chérif-Messaadia-Souk-Ahras) Examinateur 10/10/2016 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. Ce travail de thèse a été réalisé entre le Laboratoire d’Obtention de Substances Thérapeutiques, Département de Chimie, Faculté des Sciences Exactes de l’Université des Frères Mentouri-Constantine, sous la direction du Professeur Zahia KABOUCHE. Je tiens à exprimer toute ma reconnaissance et profonde Madame le Professeur Zahia KABOUCHE ma directrice de thèse pour m’avoir accueillie dans le laboratoire d’Obtention de Substances Thérapeutiques, et surtout pour la confiance qu’elle m’a accordée dans la réalisation de ce travail, sa disponibilité, ses conseils éclairés et son concours constant dans cette thèse. Je tiens à adresser mes remerciements et exprimer ma gratitude aux membres de Jury qui ont accepté de juger ce travail malgré leurs multiples occupations : Professeur Ahmed KABOUCHE (Université des frères Mentouri-Constantine), en qualité de président. Professeur Salah AKKAL (Université des frères Mentouri-Constantine), en qualité d’examinateur. Professeur Ammar ZELLAGUI (Université Larbi Ben M'hidi - Oum El-Bouaghi), en qualité d’examinateur. Professeur Abdelmalik BELKHIRI (Université des frères Mentouri-Constantine), en tant qu’examinateur. Docteur Nadji BOULEBDA (Université Mohamed Chérif-Messaadia-Souk-Ahras), en qualité d’examinateur. Je tiens à remercier plus particulièrement : Monsieur le Professeur Hiroshi ARAYA Université Meiji-Japon, en m’accueillant dans son équipe, pour sa disponibilité, ses conseils, et pour m’avoir donné l’opportunité et d’avoir dirigé une partie de ce travail. Monsieur le Professeur Mehmet ÖZTÜRK Université Sitki Koçman-Turquie, pour m’avoir accueillie au sein de son laboratoire, afin de réaliser la partie biologique de ma thèse. Je remercie mes amis de Turquie Ebru et Yunus, du Japon Naoko, Yoshiko, Higashiyama, Masahuro et Suzuna qui ont rendu cette belle aventure plus agréable. Un grand merci pour les bons moments partagés, votre bonne humeur, votre disponibilité, votre aide et soutien moral. L’ensemble de mes collègues du laboratoire d’Obtention de Substances Thérapeutiques trouvera ici l’expression de toute ma sympathie, pour avoir su me soutenir et m’encourager au cours de ce travail. Finalement, toute ma gratitude va à mes parents qui n’ont jamais douté de moi et qui m’ont aidée et encouragée tout au long de mes études, à mes frères et sœurs pour leur patience et leur soutien pendant la période ardue qu’est la rédaction. A l’issue de ce travail, j’ai l’immense plaisir de remercier tous ceux qui ont permis sa réalisation dans des conditions exceptionnelles. Cette thèse est dédiée… À mes chers parents À mes sœurs Radhia et Ikram À mes frères Mohamed et Radhouane À mon neveu Kossai À tous mes amis et collègues Maria Table de matières Introduction générale………………………………………………………………………. 2 Partie 1 : Revue Bibliographique………………………………………………………… 4 Chapitre 1 : Aperçu bibliographique sur le genre Mentha ………….……………...... 5 1.1. Introduction……….……………………………………………………………… 6 1.2. Position systématique de la famille des Lamiaceae……………………………… 6 1.3. Présentation du genre Mentha et de l’espèce Mentha aquatica L.……………….. 6 1.4. Utilisation en médecine traditionnelle du genre Mentha….……………………… 7 1.5. Activités biologiques reconnues du genre Mentha ……………………………… 10 1.6. Métabolites isolés du genre Mentha……………………………………………… 12 1.7. Métabolites secondaire de l’espèce Mentha aquatica L.………………………… 19 Chapitre 2 : Aperçu bibliographique sur le genre Stachys…………………………… 22 2.1. Introduction……………………………………………………………………...… 23 2.2. Caractéristiques botanique de Stachys guyoniana………………………………… 23 2.3. Utilisation en médecine traditionnelle du genre Stachys de Noé...……………….. 23 2.4. Activités biologiques reconnues du genre Stachys……………………………….. 24 2.5. Métabolites secondaire principaux du genre Stachys………………………………… 26 2.5.1. Flavonoïdes…………………………..………………………………………. 26 2.5.2. Iridoïdes……………………………………………………………………… 27 2.5.3. Terpénoïdes………………………………………………………………….. 29 2.5.4. Triterpénoïdes……………………………………………………………….. 33 Chapitre 3 : Aperçu bibliographique sur les huiles essentielles du genre Thymus….. 34 3.1. Introduction ………………………………………………………………………. 35 3.2. Caractéristiques botanique de Thymus dreatensis Batt…………………………… 35 3.3. Utilisation en médecine traditionnelle du genre…………………………………... 35 3.4. Activités biologiques reconnues du genre Thymus………………………………... 35 3.5. Travaux antérieurs sur les huiles essentielles du genre Thymus………………….. 36 3.5.1. Généralités sur les huiles essentielles………………………………………... 43 3.5.2. Méthodes d’extractions………………………………………………………. 43 3.5.2.1. L’hydrodistillation………………………………………………………. 43 3.5.2.2. Extraction par micro-ondes……………………………………………... 44 3.5.2.3. Extraction par le gaz supercritique……………………………………… 45 3.5.2.4. Extraction assistée par ultrasons………………………………………… 45 3.5.2.5. Extraction par solvants volatils…………………………………………. 46 Chapitre 4 : Activités biologiques………………………………………………………. 47 4. Introduction…………………………………………………………………………. 48 4.1. Radicaux libres……………………………………………………………………. 48 4.2. Activité antioxydante……………………………………………………………… 49 4.2.1. Les antioxydants …………………………………………………………….. 49 4.2.1.1. Les antioxydants naturels……………………………………………………… 49 4.2.1.2. Les antioxydants de synthèse…………………………………………………. 53 4.2.2. Les méthodes les plus fréquemment utilisées pour l’évaluation de l’activité 54 antioxydante……………………………………………………………………….. 4.2.2.1. Méthode du DPPH• ……………………………………………………. 54 4.2.2.2. Piégeage de l’ABTS+• ………………………………………………….. 55 4.2.2.3. Méthode du CUPRAC………………………………………………….. 56 4.2.2.4. Chélation des ions métalliques………………………………………….. 56 4.2.2.5. Blanchissement du β-carotène…………………………………………... 57 4.3. Dosage des polyphénols………………………………………………………….. 57 4.4. Screening chimique………………………………………………………………. 57 4.5. Activité Anticholinesterase………………………………………………………... 57 4.6. Activité Antibactérienne…………………………………………………………... 60 4.6.1. Technique de diffusion en milieu gélosé (antibiogramme)………………….. 60 4.6.2. Détermination de la concentration minimale inhibitrice (CMI)…………….. 60 Partie 2 : Matériel et Méthodes…………………………………………………………….. 62 Chapitre 1 : Matériel végétal, Séparations-Extractions et analyses…….……………. 63 1.1. Matériel végétal …………………………………………………………………... 63 1.1.1. Récolte de la plante Mentha aquatica..………………………………………. 63 1.1.2. Récolte de la plante Thymus dreatensis……………..……………………….. 63 1.1.3. Récolte de la plante Stachys guyoniana……………..……………………….. 63 1.2. Extraction et séparation de la plante Mentha aquatica……………………………. 63 1.2.1. Extraction ……………………………………………………………………. 63 1.2.2. Matériel chromatographique…………………………………………………. 64 1.2.2.1. Chromatographie sur couche mince CCM……………………………… 64 1.2.2.2. Chromatographie sur colonne ouverte CC……………………………… 65 1.2.2.3. Chromatographie liquide haute performance CLHP…………………… 65 1.2.3. Purification ………………………………………………………………….. 65 1.2.3.1. Fractionnement et purification de la fraction chloroforme des parties aériennes de l’espèce M. aquatica……………………………………………. 65 1.2.3.2. Fractionnement et purification de la fraction Acétone des racines de l’espèce M. aquatica………………………………………………………….. 67 1.3. Extraction de la plante Stachys guyoniana………………………………………. 70 1.4. Hydrodistillation de l’huile essentielle de Thymus dreatensis…………………… 70 1.5. Analyses…………………………………………………………………………… 70 1.5.1. Chimie structurale……………………………………………………………. 70 1.5.1.1. Spectrophotométrie UV……….………………………………………… 70 1.5.1.2. Spectrométrie de Masse…………………………………………………. 70 1.5.1.3. Spectrométrie RMN…………………………………………................. 70 1.5.1.4. Pouvoir rotatoire………………………………………………………… 71 1.5.2. Analyses GC et GC/M……………………………………………………….. 71 1.5.2.1. Analyse GC……………………………………………………………... 71 1.5.2.2. Analyse GC/MS………………………………………………………… 71 1.5.2.3. Identification des composants de l’huile essentielle de Thymus dreatensis Batt……………………………………………………….………….. 72 Chapitre 2 : Activités biologiques………………………………………………………….. 73 2.1. Activité antioxydante…………………………………………………………….. 74 2.1.1. Blanchissement du β-carotène……………………………………………….. 74 2.1.2. Activité antiradicalaire DPPH………………………………………………... 76 2.1.3. Essai de décoloration de radical cation ABTS………………………………. 76 2.1.4. La réduction cuprique (CUPRAC)…………………………………………… 77 2.1.5. Chélation des ions ferreux……………………………………………………. 77 2.2. Détermination des phénols totaux…………………………………………………. 77 2.3. Screening chimique………………………………………………………………... 78 2.4. Activité anticholinestérase………………………………………………………... 79 2.5. Activité antibactérienne ………………………………………………………….. 79 Partie 3: Résultats
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