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1 Universite Des Sciences Et Technologies De Lille UNIVERSITE DES SCIENCES ET TECHNOLOGIES DE LILLE – LILLE 1 ECOLE DOCTORALE SCIENCES DE LA MATIERE, DU RAYONNEMENT ET DE L’ENVIRONNEMENT Doctorat Chimie Organique et Macromoléculaire Thierry HENNEBELLE INVESTIGATION CHIMIQUE, CHIMIOTAXONOMIQUE ET PHARMACOLOGIQUE DE LAMIALES PRODUCTRICES D’ANTIOXYDANTS : Marrubium peregrinum , Ballota larendana , Ballota pseudodictamnus (Lamiacées) et Lippia alba (Verbénacées) Thèse dirigée par le Pr. François BAILLEUL et Mme le Dr. Sevser SAHPAZ Equipe d’Accueil 1043 Soutenue le 24 novembre 2006 Jury : M. François BAILLEUL Professeur à la Faculté des Sciences Pharmaceutiques et Biologiques de Lille 2 M. Joël BOUSTIE Professeur à la Faculté de Pharmacie de Rennes 1 M. Jean-Louis HILBERT Professeur à l’Université des Sciences et Technologies de Lille (Lille 1) M. Guy LEWIN Professeur à la Faculté de Pharmacie de Chatenay- Malabry (Paris-Sud 11) Mme Sevser SAHPAZ Maître de Conférences à la Faculté des Sciences Pharmaceutiques et Biologiques de Lille 2 M. Gaston VERMEERSCH Professeur à la Faculté des Sciences Pharmaceutiques et Biologiques de Lille 2 1 This wandering race, sever'd from other men, Boast yet their intercourse with human arts; The seas, the woods, the deserts, which they haunt, Find them acquainted with their secret treasures: And unregarded herbs, and flowers, and blossoms, Display undreamt-of powers when gather'd by them . The Jew (cité par Sir Walter Scott dans “Ivanhoe”) 2 Remerciements Je tiens tout d’abord à remercier mes directeurs de thèse, Monsieur le Professeur François Bailleul et Madame le docteur Sevser Sahpaz pour leur attention, leur réactivité et leur optimisme tout au long de ces trois années… et des précédentes ! Mes remerciements vont également aux autres membres du jury, qui ont bien voulu trouver un peu de temps pour évaluer mon travail : Monsieur le Professeur Jean-Louis Hilbert, Messieurs les Professeurs Joël Boustie et Guy Lewin, qui ont accepté d’être les rapporteurs de ce travail et Monsieur le Professeur Gaston Vermeersch. De nombreuses personnes m’ont apporté leur aide tout au long de cette thèse. La mise à disposition de moyens techniques, les formations et certaines discussions se sont révélées fondamentales pour l’existence de résultats et leur valorisation. Je veux exprimer ma plus profonde gratitude à tout le Laboratoire d’Application de RMN de l’Université de Lille 2 : Madame le Professeur Nathalie Azaroual, Monsieur le Professeur Gaston Vermeersch, Madame le Docteur Stéphanie Delbaere, Messieurs les Docteurs Christophe Bochu et Jérôme Berthet, Messieurs Vincent Ultre, Frédéric Bonhomme et Pierre Larzillière. Je remercie également Messieurs Paul Bourgeois (Université des Antilles et de Guyane), Charles Dermont (Institut Supérieur d’Agriculture de Lille), Henry Joseph (APLAMEDAROM), Emmanuel Nossin (AVPMC), Bernard Weniger (Université de Strasbourg) pour leur aide dans l’étude de Lippia alba ; Monsieur le Professeur François Tillequin (Paris V) et Madame le Prof. Dr. Nurten Ezer (Hacettepe Üniversitesi, Ankara) pour les collectes d’échantillons d’autres plantes. Enfin, j’exprime ma gratitude envers Monsieur le Professeur Bernard Gressier et Madame le Docteur Françoise Martin-Nizard et Mademoiselle Adeline Darchy pour la réalisation des tests biologiques. Merci également à toutes les personnes avec qui j’ai partagé paillasses, matériel, conseils techniques et/ou discussions triviales pendant des durées variables : Monsieur le bientôt Docteur Alexis Zamblé (Zamblé bi Tah), Marie Carpentier, Ahlam Azarouk, Patricia Cleenewerck, Claire Delattre, Fabienne Delebarre, Maryline Drouet, Marie Landrieux, QiaoWen Yang. Mustafa Gavdar sa ğ olsun. Dr. Irem Tatlı Çankaya’ya Ballota larendana üzerinde ki bilgilerinden dolayı çok te şekkür ederim. Merci à tout le monde au laboratoire de Pharmacognosie de la Faculté des Sciences Pharmaceutiques et Biologiques de Lille : Monsieur le Professeur Francis Trotin, Mesdemoiselles Monique Torck et Nicole Didry, Mesdames Malika Moreira Da Costa, Jennifer Rivière, Michèle Leterme ainsi que l’inénarrable Marie-Agnès Carlier. Merci à ma famille. Céline, je t’aime. Merci. 3 Table des matières Remerciements ........................................................................................................................... 3 Table des matières...................................................................................................................... 4 Abréviations, symboles et conventions...................................................................................... 9 Introduction .............................................................................................................................. 12 I. Oxydation et antioxydants .................................................................................................... 14 1.1. Action néfaste des ERO dans les tissus biologiques..................................................... 16 1.1.1. Lipides.................................................................................................................... 16 1.1.2. Protéines................................................................................................................. 19 1.1.3. Acides nucléiques................................................................................................... 19 1.2. Mécanismes physiologiques de l’inactivation des ERO ............................................... 20 1.3. Les antioxydants, sources et intérêt............................................................................... 22 1.3.1. Enzymes et cofacteurs............................................................................................ 22 1.3.2. Conservateurs alimentaires .................................................................................... 22 1.3.3. Autres utilisations industrielles .............................................................................. 24 1.3.4. Principaux antioxydants présents naturellement dans notre alimentation.............. 27 1.3.5. Médicaments antioxydants..................................................................................... 28 1.3.6. Métabolites secondaires des végétaux : avancées et potentiels.............................. 28 1.3.6.1. Polyphénols ..................................................................................................... 29 1.3.6.2. Terpènes .......................................................................................................... 31 1.3.6.2.1. Monoterpènes ........................................................................................... 32 Monoterpènes volatils et autres constituants des huiles essentielles.................... 32 Monoterpènes iridoïdiques................................................................................... 34 1.3.6.2.2. Diterpènes................................................................................................. 35 II. Etude de plantes potentiellement productrices d’antioxydants ........................................... 37 2.1. Les Lamiales ................................................................................................................. 37 2.1.1. Place dans la classification systématique botanique .............................................. 37 2.1.2. La famille des Lamiacées....................................................................................... 38 A. Le genre Marrubium et l’espèce Marrubium peregrinum L................................... 39 1. Aspects botaniques............................................................................................... 39 1.1. Caractéristiques du genre Marrubium ........................................................... 39 1.2. Marrubium peregrinum ................................................................................. 40 Caractères morphologiques........................................................................ 40 Répartition géographique ........................................................................... 40 Synonymie.................................................................................................. 41 2. Travaux antérieurs sur Marrubium peregrinum ................................................... 41 2.1. Composition chimique .................................................................................. 41 2.1.1. Huile essentielle ............................................................................... 41 2.1.2. Diterpènes......................................................................................... 42 2.1.3. Stérols............................................................................................... 43 2.1.4. Flavonoïdes ...................................................................................... 44 2.1.5. Phénylpropanoïdes ........................................................................... 45 2.2. Essais pharmacologiques............................................................................... 45 3. Travaux personnels .............................................................................................. 46 3.1. Isolement des composés................................................................................ 46 3.2. Identification des composés .......................................................................... 47 Diterpènes................................................................................................... 47 Composé 1..............................................................................................
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