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Etude Phytochimique Et Activités Biologiques Des Huiles Essentielles Et Des REPUBLIQUE ALGERIENNE DEMOCRATIQUE ET POPULAIRE الجمهورية الجزائرية الديمقراطية الشعبية MINISTERE DE L’ENSEIGNEMENT SUPERIEUR ET DE LA RECHERCHE SCIENTIFIQUE وزارة التعليم العالي و البحث العلمي ECOLE NATIONALE SUPERIEURE AGRONOMIQUE EL-HARRACH –ALGER المدرسة الوطنية العليا للفﻻحة الحراش -الجزائر- DEPARTEMENT DE TECHNOLOGIE ALIMENTAIRE Thèse En vue de l’obtention du diplôme de Doctorat en Sciences Agronomiques Option : Sciences Alimentaires Thème Etude phytochimique et activités biologiques des huiles essentielles et des extraits éthanoliques de Teucrium polium subsp capitatum, Thymus algeriensis et Ammoides verticillata Présentée par : M. BENDJABEUR Salah Jury : Président : M. BENCHABANE A. Professeur (E.N.S.A. El Harrach) Directeur de thèse : M. BITAM A. Professeur (E.N.S.A. El Harrach) Co-directeur : M. HAZZIT M Professeur (E.N.S.A. El Harrach) Examinateurs : M. FERHAT M. A. Professeur (ENS Kouba) M. AIT-OUAZZOU A. Maitre de conférences A (Univ. d’Alger 1) Mme. DOUZANE M. Maitre de recherche A (INRA Alger) Année universitaire : 2018-2019 Remerciements Louange à Allah le tout puissant qui m’a donné la santé, le courage, la volonté et la patience pour que je puisse réaliser ce travail. J’exprime mes sincères remerciements à M. BITAM Arezki et M. HAZZIT Mohammed, professeurs à l’Ecole Nationale Supérieure Agronomique (ENSA) pour m’avoir accordé leur confiance en acceptant de diriger ce travail. Qu’ils trouvent ici l’expression de ma reconnaissance et mon profond respect. Je tiens à remercier M. BENCHABANE Ahmed, Professeur à l’ENSA, qui m’a fait l’honneur d’accepter la présidence de mon jury de thèse. Qu’il trouve ici l’expression de ma grande considération. Mes sincères remerciements vont également à : - M. FERHAT Mohamed El Amine, Professeur à l’Ecole Normale Supérieure (ENS) de Kouba (Alger). - M. AIT OUAZZOU Abdennour Maitre de conférences A à l’Université d’Alger 1. - Mme. DOUZANE Malika, Maitre de recherche A à l’Institut National de la Recherche Agronomique (INRA) d’Alger. d’avoir accepté de faire partie du jury d’examination de cette thèse. Ce travail n’aurait pas pu voir la lumière du jour sans l’aide précieuse des personnes suivantes : . Dr. BENSOUICI Chawki, responsable de laboratoire de Biochimie, Centre de Recherche en Biotechnologie (CRBT) de Constantine. Mme. MERDACI Amel, responsable de laboratoire de Microbiologie Centre de Recherche en Biotechnologie (CRBT) de Constantine. L’ensemble du personnel du département de technologie alimentaire et nutrition humaine. Enfin, j’exprime ma profonde gratitude à toutes les personnes qui ont contribué de près ou de loin au bon déroulement de ce travail et que j’ai peut-être omis de citer. Liste des figures Figure 1 : Structure chimique d’unité Isoprène (2-méthylbuta-1,3-diène)................ 6 Figure 2 : Structure chimique de quelques composés d’huiles essentielles ………. 9 Figure 3 : Schéma biosynthèse des terpènes et des phénylpropanoides………….... 11 Figure 4 : Structure commune des acides phénoliques…………………………...... 14 Figure 5 : Structure générique d’une molécule de flavonoïde ………...................... 15 Figure 6 : Voie métabolique possible des composés phénoliques………………..... 18 Figure 7 : Schéma des principales voies de la biosynthèse des polyphénols…….... 20 Figure 8 : Feuilles et fleurs de Teucrium polium subsp capitatum………………… 21 Figure 9 : Feuilles et fleurs de Thymus algeriensis………………………………... 26 Figure 10 : Feuilles et fleurs d’Ammoides verticillata……………………………..... 31 Figure 11 : Sources cellulaires de production des ERO …………………………..... 35 Figure 12 : Stress oxydatif induit par les ERO…………………………………….... 38 Figure 13 : Effets de l'oxydation des lipides sur la qualité des aliments……………. 42 Figure 14 : Stabilisation par résonance du radical phénoxyle……………………..... 46 Figure 15 : Hydrolyse de l'acétylcholine catalysée par l'acétylcholinestérase……..... 49 Figure 16 : Représentation schématique du site actif de l’AChE …………………... 50 Figure 17 : Structure de quelques inhibiteurs réversibles ……………….………….. 53 Figure 18 : Structure de quelques inhibiteurs réversibles ……………….………….. 56 Figure 19 : Structure chimique générale des carbamates biologiquement actifs …… 56 Figure 20 : Étapes de l'interaction d'une estérase avec un inhibiteur organophosphoré……….………….………….………….……………. 57 Figure 21 : Formule structurelle générale des organophosphorés …........................... 57 Figure 22 : Sites d'une bactérie dans lesquels des composés naturels sont actifs …... 63 Figure 23 : Echantillons de plantes sèches utilisées dans l’extraction…………….... 69 Figure 24 : Réaction entre le radical DPPH• et l’antioxydant pour former le DPPH stable …………………………………………………………………..... 73 •+ Figure 25 : Formation de l’ABTS par un oxydant persulfate de potassium ……..... Figure 26 : Illustration de la méthode d'aromatogramme…………………………… 82 Figure 27 : Préparation d'inoculum microbien McFarland………………………...... 83 Figure 28 : Microdilution en bouillon pour le test antibactérien……………………. 83 Figure 29 : Chromatogramme (agrandi) GC-MS de l’huile essentielle de Teucrium polium subsp capitatum……………………………………………….... 89 Liste des figures Figure 30 : Chromatogramme (agrandi) GC-MS de l’huile essentielle de Thymus algeriensis…………………………………………………………….... 93 Figure 31 : Chromatogramme (agrandi) GC-MS de l’huile essentielle d’Ammoides verticillata……………………………………………………………………... 96 Figure 32 : Schéma de biosynthèse de carvacrol et de thymol……………………... 96 Figure 33 : Chromatogramme HPLC-DAD-UV à 355nm de l’extrait de Teucrium polium subsp capitatum………………………………………………… 102 Figure 34 : Chromatogramme HPLC-DAD-UV à 355nm de l’extrait de Thymus algeriensis……………………………………………………………………… 103 Figure 35 : Chromatogramme HPLC-DAD-UV à 355nm de l’extrait d’Ammoides verticillata……………………………………………………………………… 105 Figure 36 : Activité d’inhibition de l’acétylcholinestérase (AChE) exprimée en pourcentages…………………………………………………………… 107 Figure 37 : Activité d’inhibition de la butyrylcholinestérase (BChE) exprimée en pourcentages…………………………………………………………… 107 Figure 38 : Pouvoir de piégeage du radical DPPH exprimé en pourcentage d’inhibition (%)…………………………………………………………. 114 Figure 39 : Pouvoir de piégeage du radical ABTS exprimé en pourcentage d’inhibition (%)…………………………………………………………. 117 •– Figure 40 : Activité du piégeage du radical superoxyde (O2 ) exprimée en % de réduction en formazan…………………………………………………... 119 Figure 41 : Pouvoir réducteur du fer exprimé en absorbance à 700nm……………… 121 Figure 42 : Pouvoir réducteur cuivrique (CUPRAC) exprimé en absorbance à 450 nm……………………………………………………………………… 125 Figure 43 : Activité d’inhibition de blanchissement de β-carotène en exprimée en pourcentages…………………………………………………………… 127 Figure 44 : Activité antihémolytique exprimée en % d’inhibition d’hémolyse induite par AAPH……………………………………………………………….. 131 Figure 45 : Photos montrant les zones d’inhibitions des souches testées (aromatogramme)………………………………………………………. 141 Figure 46 : Représentation schématique de l'activité supposée du carvacrol………. 144 Liste des tableaux Tableau 1 : Principales fonctions monoterpéniques des HEs……………………... 7 Tableau 2 : Principales fonctions sesquiterpéniques des HEs…………………….. 8 Tableau 3 : Structure des squelettes des polyphénols…………….………………. 13 Tableau 4 : Différentes classes de flavonoïdes et leurs sources alimentaires…….. 16 Tableau 5 : Espèces réactives de l’oxygène (ERO) et espèces non radicalaires….. 34 Tableau 6 : Mécanismes d’oxydation des lipides…………………………………. 40 Tableau 7 : Principaux groupes de composés de plantes avec leurs mécanismes antimicrobiens……………………………………………………...… 61 Tableau 8 : Données sur les composés étalons utilisés pour l’identification HPLC 72 Tableau 9 : Liste et caractéristiques des souches microbiennes testées…………... 81 Tableau 10 : Composition chimique (%) de l’huile essentielle de Teucrium polium subsp capitatum……………………………………………………………… 87 Tableau 11 : Composition chimique (%) de l’huile essentielle de Thymus algeriensis…………………………………………………………….. 91 Tableau 12 : Composition chimique (%) de l’huile essentielle d’Ammoides verticillata……………………………………………………………………. 95 Tableau 13 : Rendement, teneur en composés phénoliques totaux (CPT) et en flavonoïdes totaux (FT)……………………………………………….. 98 Tableau 14 : Composition chimique (%) des extraits éthanoliques des plantes étudiées……………………………………………………………… 101 Tableau 15 : Effet inhibiteur des huiles essentielles et des extraits éthanoliques sur BChE et AChE exprimé en IC50 (µg / ml)…………………………… 106 Tableau 16 : Activité antiradicalaire des huiles essentielles et des extraits éthanoliques exprimée en IC50 (µg / ml)………………………...…… 113 Tableau 17 : Pouvoir réducteur ferrique et cuivrique et pouvoir d’inhibition de blanchiment du -carotène IC50 (µg/ml)……………………………… 122 Tableau 18 : Effet inhibiteur des extraits éthanoliques vis-à-vis de l’hémolyse exprimé en IC50 (µg / ml)……………………………………………… 130 Tableau 19 : Diamètres des zones d’inhibition (ZI en mm) et concentrations minimales inhibitrices (CMI en µg/ml)) des huiles essentielles………. 135 Liste des abréviations ABTS : 2,2'-azino -bis (acide 3-éthylbenzthiazoline-6-sulfonique AAPH : 2,2-azobis (2-méthylpropionamidine) dihydrochlorure de composé azoïque ACh : Acétylcholine AChE : Acétylcholinestérase AG : Acides gras AGPI : Acides gras polyinsaturés AGS : Acides gras saturés ATCC : American Type Culture Collection A. ver : Ammoides verticillata BChE : Butyrylylcholinestérase BHA : Butyl-Hydroxy-Anisole BHT : Butyl-Hydroxy-Toluène CMI : Concentration Minimale Inhibitrice CAT : Catalase CLSI : Clinical and Laboratory Standards Institute CPT
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