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THÈSE LMD Présentée À REPUBLIQUE ALGERIENNE DEMOCRATIQUE ET POPULAIRE MINISTERE DE L’ENSEIGNEMENT SUPERIEUR ET DE LA RECHERCHE SCIENTIFIQUE UNIVERSITE ABOU-BEKR BELKAID – TLEMCEN THÈSE LMD Présentée à : FACULTE DES SCIENCES – DEPARTEMENT DE CHIMIE Pour l’obtention du diplôme de : DOCTORAT Spécialité: CHIMIE DES PRODUITS NATURELS, ANALYSES ET APPLICATIONS Par : Mme Fatima Zahra BENOMARI Sur le thème VARIABILITE CHIMIQUE ET ACTIVITES BIOLOGIQUES DES VOLATILS DES ESPECES AROMATIQUES A INTERET ECONOMIQUE DES GENRES MENTHA, INULA, THYMUS, ASTERICUS ET CHRYSANTHEMUM DE L’OUEST ALGERIEN Soutenue publiquement le 30 Avril 2018 à Tlemcen devant le jury composé de : Mr Boufeldja TABTI Professeur Université de Tlemcen Président Mr Nassim DJABOU Maître de Conférences A Université de Tlemcen Directeur de thèse Mr Cédric BERTRAND Professeur Université de Perpignan Examinateur Mr Chaouki SELLES Professeur Université de Tlemcen Examinateur Mr David DUVAL Maître de Conférences A Université de Perpignan Examinateur Mme Zahia HOUMANI Professeur Université de Blida Invitée Mr Hamdane ALLALOU Président Consortium PPAM&HE Invité Mr Mohamed MOUMANI Directeur Parc National de Tlemcen Invité Laboratoire de Chimie Organique Substances Naturelles et Analyses BP 119, 13000 Tlemcen - Algérie SOMMAIRE Parti A INTRODUCTION ……………………………………………………………………………………………….P1 1. Plantes à Parfum Aromatiques et Médicinales (PPAM) …………………………………………………P2 2. Généralités sur les huiles essentielles ……………………………………………………………………...P3 3. Les hydrolats ………………………………………………………………………………………………..P4 4. Intérêt économique …………………………………………………………………………………………P5 4.1. Les Plantes à Parfum Aromatiques et Médicinales ……………………………………………….....P5 4.2. Les Huiles Essentielles …………………………………………………………………………………P5 5. Problématique de recherche ………………………………………………………………………………P7 Partie B ETUDE BIBLIOGRAPHIQUE ………………………………………………………………………………..P12 1. Famille des Lamiacées ……………………………………………………………………………………..P13 1.1. Genre Mentha ………………………………………………………………………………………….P13 1.1.1. Mentha pulégium (menthe pouliot)……………………………………………………………………P14 1.1.2. Mentha rotundifolia (menthe des champs) …………………………………………………………...P15 1.1.3. Mentha pipérita (la menthe poivrée) ………………………………………………………………….P16 1.1.4. Mentha spicata (menthe verte) ………………………………………………………………………..P17 1.2. Genre Thymus ………………………………………………………………………………………….P18 1.2.1. Thymus ciliatus …………………………………………………………………………………………P19 1.2.1.1. Thymus ciliatus ssp eu-ciliatus …………………………………………………………………...P19 1.2.1.2. Thymus ciliatus ssp coloratus ……………………………………………………………………..P20 1.2.1.3. Thymus ciliatus ssp munbyanus ………………………………………………………………..P20 1.2.2. Thymus inodorus (Micromeria inodora) ………………………………………………………………P21 2. Famille des Astéracées ……………………………………………………………………………………...P22 2.1. Genre chrysanthemum …………………………………………………………………………………P23 2.1.1. Chrysanthemum coronarium …………………………………………………………………………..P24 2.2. Genre Inula ……………………………………………………………………………………………..P25 2.2.1. Inula viscosa …………………………………………………………………………………………….P25 2.2.2. Inula montana …………………………………………………………………………………………..P26 2.3. Genre Asteriscus ………………………………………………………………………………………..P27 2.3.1. Asteriscus maritimus (Pallenis maritima)………………………………………………………………P27 2.3.2. Asteriscus spinosus (Pallenis spinosa)………………………………………………………………...P28 Partie C L’ANALYSE DES MELANGES COMPLEXES DES VOLATILS DES PLANTES ……………………..P31 1. Méthodes de préparation de l’échantillon ………………………………………………………………...P32 1.1. Hydrodistillation ………………………………………………………………………………………..P33 1.2. Extraction liquide-liquide (Obtention de l’extrait d’hydrolat) ……………………………………...P34 2. Les méthodes d’identification des constituants des mélanges complexes des volatils …………………..P34 2.1. Chromatographie en phase gazeuse « CPG » ………………………………………………………...P35 2.2. Chromatographie en phase gazeuse /spectrométrie de masse (CPG/SM) ………………………….P36 2.3. Résonance magnétique nucléaire (RMN) ……………………………………………………………..P37 3. Méthodologie d’analyse……………………………………………………………………………………...P37 Partie D APPROCHE METHODOLOGIE – RESULTATS ……………………………………………………………P42 1. L’apport de la Chromatographie Liquide sur Colonne (CLC) …………………………………………..P43 2. Utilisation des bibliothèques de données commerciales, un savoir-faire à acquérir…………………….P44 3. La résonance magnétique nucléaire RMN du carbone 13 ………………………………………………..P45 4. Outil statistique ……………………………………………………………………………………………...P45 4.1. Analyse en Composante Principale (ACP)………………………………………………………………...P46 4.2. Classification Ascendante Hiérarchique (CAH) ………………………………………………………….P46 5. Compositions chimiques des huiles essentielles ……………………………………………………………P47 5.1. Variabilité Chimique (Nombre des échantillons)………………………………………………………….P47 5.2. Séchage de la plante et détermination de la teneur en eau ……………………………………………….P48 5.3. Espèces, sous-espèces et variétés…………………………………………………………………………….P49 5.3.1. Espèce ……………………………………………………………………………………………………P49 5.3.2. Sous-espèces ……………………………………………………………………………………………..P50 5.3.3. Variétés …………………………………………………………………………………………………..P50 5.4. Partie de la plante utilisée …………………………………………………………………………………..P51 5.5. Cycle végétatif de la plante et sa période de récolte ………………………………………………………P52 5.6. Facteurs environnementaux ………………………………………………………………………………..P55 6. Étude de la composition chimique des hydrolats …………………………………………………………..P56 Partie E VALORISATION DES HUILES ESSENTIELLES : ACTIVITES BIOLOGIQUES ………………………P59 1. Activité antioxydante ………………………………………………………………………………………..P60 1.1. Piégeage du radical libre DPPH (2,2-diphényle-1-picrylhydrazyl) ………………………………………P60 1.2. Réduction du fer : FRAP (Ferric Reducing Antioxidant Power) ………………………………………...P61 1.3. Test de blanchissement du β-carotène ……………………………………………………………………...P62 2. Activité antibactérienne ……………………………………………………………………………………..P65 2.1. Méthode par diffusion sur milieux solide (méthode des disques) ……………………………………...…P66 2.2. Méthode sur milieux liquides ……………………………………………………………………………….P66 3. Activité antifongique ………………………………………………………………………………………...P70 3.1. Méthode de diffusion ………………………………………………………………………………………...P71 3.2. Méthode de fumigation………………………………………………………………………………………P72 4. Activité insecticide et larvicide …………………………………………………………………………… P74 5. Activité antifongique des hydrolats ……………………………………………………………………… P77 Partie F ASPECT ECONOMIQUE ………………………………………………………………………………………P79 1. Contexte général……………………………………………………………………………………………..P80 2. Approche Intérêt Économique / Recherche Scientifique………………………………………………….P81 2.1. Huiles Essentielles jamais décrites dans la littérature ……………………………………………………P82 2.1.1. Cas de Thymus inodorus………………………………………………………………………………...P82 2.1.2. Cas d’Inula montana…………………………………………………………………………………….P82 2.2. Huiles essentielles jamais décrites en Algérie……………………………………………………………...P83 2.2.1. Cas de Thymus ciliatus ssp manbyanus………………………………………………………………...P83 2.2.2. Cas d’Asteriscus maritimus et d’Asteriscus spinosus…………………………………………………..P83 2.3. Huiles essentielles décrites en Algérie et dans le monde…………………………………………………..P83 CONCLUSIONS ………………………………………………………………………………………………….P88 REFERENCES ……………………………………………………………………………………………………P90 LISTE DES TRAVAUX …………………………………………………………………………………………P103 LISTE DES ARTICLES SCIENTIFIQUES ……………………………………………………………….......P108 ARTICLE 1 ………………………………………………………………………………………………………P ARTICLE 2 ………………………………………………………………………………………………………P ARTICLE 3 ………………………………………………………………………………………………………P ARTICLE 4 ………………………………………………………………………………………………………P ARTICLE 5 ………………………………………………………………………………………………………P اﺰﻮت اﻷﺎﺔ ھﻲ ﺎت طﺔ ذات ﺔ ﻀﺎﺔ ﺎﺔ، ﮭﻲ ﺪم ﺎﺔ ﺎﮭﺎ اﻄﺮة، ﻲ ﻄﺎع ﻀﺮات ا واﻄﻮر، و ﺎﺔ أﺮى ﺎﮭﺎ اﻄﺔ. اﺰﻮت اﻷﺎﺔ ذات ﺮ ﺎﻲ ﺪ ﺪا. ﺈﮭﺎ ﺪم أﺎﺎ ﺎ إﻰ ﺪة ﺎت اﺰﺎت اﻄﺮﺔ اﺸﻄﺔ، واﻲ ﻮﺪ ﻲ ﺔ واﻲ ﻄ .ﺬ أﺪث أﺎ اﻀﺮ وا ﺪ ھﺬا اﺚ إﻰ دراﺔ ا اﺎﻲ ﺾ اﻷﻮاع اﺸﺮﺔ اﺰاﺮ واﺎ، أ إﺸﺎء دراﺎت ﺎرﺔ، و أﻀﺎ اﻷﻮاع اﻮطﺔ اﻄﺔ اﻐﺮﺔ اﺰاﺮ واﻲ ﺪرس ﻻول ﺮة، ﺪﺪ ﺮﺎﮭﺎ .واﺸ أي ﻮﺔ اﻲ ﺪ ﺰ ﺮﮭﺎ اﺎﻲ، وﮭ اﺎ اﺎﻲ اﮭﺪف ھﺬه اﺪراﺔ ﺮﺰ ﮭﺔ ﻲ اﺎھﺔ ﻲ ﻄﻮﺮ اﻮﺎت اﺎﺔ ﺎﺜﺮوة اﺎﺔ،و ﮭﺔ اﺮى ﺪراﺔ اﺎدﺔ اﺎﺪة اﻲ أن ﮭﺎ ﺔ ﺾ اﻷﻮاع اﺪروﺔ ﻲ ھﺬه اﻷطﺮوﺔ ﻰ اﻄﺎق اﺎﻲ اﺔ اﻀﺎﺔ اﻻﺎﺔ واﻻﺎدﺔ Résumé Les huiles essentielles sont des produits naturels à forte valeur ajoutée, elles sont utilisées, d’une part pour leurs propriétés odorantes, dans le secteur des cosmétiques et parfums, et d’autre part pour leurs propriétés médicinales. Les huiles essentielles sont d’une composition chimique très complexe; elles proposent parfois jusqu’à plusieurs centaines de molécules aromatiques actives, qui se trouvent en proportions variables et qui nécessitent la mise en œuvre des méthodes de préparations et d’analyses les plus modernes. Ce travail de thèse, repose sur l’étude de la variabilité chimique de certaines espèces communes à l’Algérie et dans le monde, afin d’établir des études comparatives, mais aussi des espèces endémiques de la région Ouest de l’Algérie, jamais décrites dans la littérature, afin d’identifier leurs compositions chimiques et de déceler toute spécificité pouvant caractériser leurs compositions chimiques et ainsi intéresser le monde industriel. Pour cela différents volets ont été développé : le principal volet est chimique, il concerne la caractérisation des compositions chimiques des huiles essentielles, et les deux autres volets sont complémentaires, un volet d’activités biologiques, et un volet sur l’étude économique qui montre l’importance ou l’utilité que peut apporter le développement de certaines des espèces étudiées dans cette thèse à l’échelle industrielle afin de créer de la plus-value socio- économique. Abstract Essential oils are natural products with high added value; they are used, on the one hand for their fragrant properties, in the cosmetics and
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