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Thesis Reference Thesis Isolement de xanthones et coumarines inhibitrices de l'acétylcholinestérase, respectivement à partir de "Gentianella campestris" (L.) Börner et "Gentianella amarella" (L.) Börner ssp. "acuta" (Michx.) J.M. Gillett (Gentianaceae), et "Peucedanum ostruthium" (L.) Koch (Apiaceae) URBAIN, Aurélie Abstract Lors d'un criblage visant à détecter des extraits végétaux présentant une activité inhibitrice de l'acétylcholinestérase, trois espèces se sont révélées significativement actives; deux Gentianaceae: "Gentianella campestris" et "Gentianella amarella" ssp. "acuta", et une Apiaceae: "Peucedanum ostruthium". Les composés d'intérêt ont été isolés essentiellement par chromatographie de partage centrifuge. Dix xanthones - dont deux nouvelles, notamment une xanthone dimérique - ainsi qu'un flavonoïde C- glycosylé ont été caractérisés à partir des deux espèces de gentiane. De la même manière, le fractionnement bioguidé de l'extrait de racines de "Peucedanum ostruthium" a conduit à l'obtention de cinq coumarines et d'une chromone. Parmi les dix-sept composés isolés, une xanthone - le triptexanthoside C - et trois coumarines ont montré une inhibition de l'enzyme particulièrement intéressante. L'ostruthol s'est notamment révélé dix fois plus puissant que la galanthamine lors de tests "in vitro", activité confirmée " in vivo" chez la souris. Reference URBAIN, Aurélie. Isolement de xanthones et coumarines inhibitrices de l'acétylcholinestérase, respectivement à partir de "Gentianella campestris" (L.) Börner et "Gentianella amarella" (L.) Börner ssp. "acuta" (Michx.) J.M. Gillett (Gentianaceae), et "Peucedanum ostruthium" (L.) Koch (Apiaceae). Thèse de doctorat : Univ. Genève, 2007, no. Sc. 3934 URN : urn:nbn:ch:unige-5159 DOI : 10.13097/archive-ouverte/unige:515 Available at: http://archive-ouverte.unige.ch/unige:515 Disclaimer: layout of this document may differ from the published version. 1 / 1 UNIVERSITE DE GENEVE FACULTE DES SCIENCES Section des Sciences Pharmaceutiques Laboratoire de Pharmacognosie et Phytochimie Professeur Kurt Hostettmann Isolement de xanthones et coumarines inhibitrices de l’acétylcholinestérase, respectivement à partir de Gentianella campestris (L.) Börner et Gentianella amarella (L.) Börner ssp. acuta (Michx.) J.M.Gillett (Gentianaceae), et Peucedanum ostruthium (L.) Koch (Apiaceae) THESE présentée à la Faculté des sciences de l’Université de Genève pour obtenir le grade de Docteur ès sciences, mention interdisciplinaire par Aurélie Urbain de Reims (France) Thèse N° 3934 GENEVE Atelier de reproduction de la Section de Physique 2007 REMERCIEMENTS Je tiens à exprimer ma reconnaissance à Monsieur le Professeur Kurt Hostettmann, mon directeur de thèse, pour la confiance qu’il m’a accordée en m’accueillant au sein de son équipe ; d’une part pour mener à bien le sujet de recherche qu’il m’a confié, mais également pour assurer l’enseignement et l’encadrement des étudiants en Pharmacie. J’ai apprécié son dynamisme et son enthousiasme communicatifs, ainsi que la liberté qu'il m’a accordée. Je le remercie également pour m’avoir donné l’opportunité de présenter mes travaux lors de congrès internationaux et pour m’avoir encouragée à les publier. Je remercie chaleureusement mon responsable technique, Monsieur le Docteur Andrew Marston, pour sa disponibilité, ses précieux conseils, et pour m’avoir initiée aux joies de la CPC. J’ai apprécié sa gentillesse et ses encouragements tout au long de ce travail. Ma reconnaissance va également aux membres du jury : Monsieur le Docteur Bruno David – des Laboratoires Pierre Fabre, Monsieur le Professeur Robert Anton – du Laboratoire de Pharmacognosie de l’Université Louis Pasteur de Strasbourg, Monsieur le Docteur Laurent Décosterd – du Service de Pharmacologie clinique du CHUV, et Monsieur le Professeur Jean-Luc Veuthey – du Laboratoire de Chimie Analytique Pharmaceutique de l'Université de Genève. J’ai apprécié l’attention et l’intérêt qu’ils ont porté à mon travail. Je remercie également Monsieur le Professeur Pierre-Alain Carrupt pour avoir présidé ce jury. Ce travail aurait été incomplet sans la mise en place de collaborations essentielles, permettant notamment d’approfondir la partie pharmacologique de cette étude. Pour cela, je remercie vivement le Professeur Pierre-Alain Carrupt du Laboratoire de Chimie Thérapeutique – groupe Pharmacochimie, de l’Université de Genève, ainsi que son équipe ; Saviana di Giovanni et Liliana Sintra Grilo, qui ont effectué les tests d’inhibition de l’acétylcholinestérase en solution, ainsi que Juan Bravo pour la mesure de l’inhibition des monoamine oxydases. Toute ma gratitude va au Professeur Elaine Elisabetsky et au Docteur Ionara Siqueira du Département d’Ethnopharmacologie de l’Université Fédérale de Rio Grande do Sul, Porto Alegre, Brésil, pour avoir réalisé les essais in vivo sur les souris. Merci également au Docteur Emma Marsden-Edwards, de la société Waters, à Manchester, Royaume-Uni, pour avoir développé les conditions d’analyse par UPLC/TOF. Je remercie également les diplômants qui ont contribué de près ou de loin à cette étude : Dounia et Valentin pour leur travail sur l’impératoire, Sophie et Line pour avoir entrepris avec beaucoup de ténacité l’investigation de Pancratium littorale , ainsi que Céline, ma “disciple”, pour sa bonne humeur permanente. Pour leur aide précieuse tout au long de ce travail, leurs conseils, leurs encouragements, mais aussi leur sympathie, je tiens vivement à remercier le Professeur Jean-Luc Wolfender et le Docteur Emerson Ferreira Queiroz. Merci également au Docteur Karine Ndjoko-Ioset pour m’avoir assistée lors de mes premiers pas avec la RMN et la spectrométrie de masse. Ces quatre années de thèse ont été l’occasion de nombreux échanges scientifiques avec mes collègues de l’Institut, mais également de souvenirs mémorables lors des congrès et sorties. Aussi je tiens à les remercier pour tout cela. Un merci tout spécial aux membres du “labo des blondes”, et à Aline avec qui j’ai partagé la dernière ligne droite. Je tiens aussi à remercier particulièrement Elia et Gaétan, non seulement pour leur aide technique et scientifique, mais également pour leur sympathie et leur soutien. Merci Gaétan pour les instants de complicité que nous avons partagés, et aussi pour avoir été là dans les moments, disons, “moins faciles”. Un grand merci à mes amis et collègues du LCAP pour leur bonne humeur et tous les bons moments passés ensemble. Sans vouloir froisser ceux que je ne cite pas, je souhaite remercier plus particulièrement Myriam, Laurent et Davy pour leur amitié. Pour m’avoir supportée durant ces longues années, je tiens sincèrement à remercier ma sœur Alexandra, ainsi que Benoît, Pascal et Camille. La vie ici aurait été différente sans vous. Merci aussi à tous mes amis de Haute-Savoie, de Reims et d’ailleurs pour leur soutien et leurs encouragements. Dans le désordre : Houda, Leïla, Cédric, Julian, Sébastien, Jérôme, Jean-Michel, Olivier, Hanan, Tim, Pierre-François, … Enfin je ne saurais oublier mes parents, qui m’ont soutenue et fait confiance tout au long des mes études. COMMUNICATIONS ET PUBLICATIONS Ce travail de thèse a été réalisé à l’Institut de Phytochimie et Pharmacognosie de l’Université de Lausanne d’octobre 2003 à août 2004, et au Laboratoire de Phytochimie et Pharmacognosie de l’Université de Genève de septembre 2004 à septembre 2007. Une partie des résultats obtenus a été présentée sous forme de posters dans différents congrès, et fait l’objet de plusieurs publications scientifiques. Publications Urbain A., Marston A., Queiroz E.F., Ndjoko K., Hostettmann K. Xanthones from Gentiana campestris as new acetylcholinesterase inhibitors. Planta Medica 2004, 70: 1011-1014. Urbain A., Marston A., Hostettmann K. Coumarins from Peucedanum ostruthium as inhibitors of acetylcholinesterase. Pharmaceutical Biology 2005, 43: 647-650. Hostettmann K., Borloz A., Urbain A., Marston A. Natural product inhibitors of acetylcholinesterase. Current Organic Chemistry 2006, 10: 825-847. Di Giovanni S., Borloz A., Urbain A., Marston A., Hostettmann K., Carrupt P.A., Reist M. In vitro screening assays to identify natural or synthetic acetylcholinesterase inhibitors: Thin layer chromatography versus microplate methods. European Journal of Pharmaceutical Sciences 2008 . Sous presse. Urbain A., Marston A., Sintra Grilo L., Bravo J., Purev O., Purevsuren B., Batsuren D., Reist M., Carrupt P.A., Hostettmann K. Xanthones from Gentianella amarella ssp. acuta with acetylcholinesterase and monoamine oxidase inhibitory activities. Journal of Natural Products 2008. Sous presse. Urbain A., Marston A., Batsuren D., Purev O., Hostettmann K. Preparative isolation of closely-related xanthones from Gentianella amarella ssp. acuta by centrifugal countercurrent chromatography. Phytochemical Analysis . Soumis. Urbain A., Marsden-Edwards E., Marston A., Hostettmann K. UPLC/ESI-TOF-MS as a chemotaxonomic tool for the analysis of Gentianaceae species. Phytochemical Analysis . Soumis. Posters Urbain A., Marston A., Queiroz E.F., Ndjoko K., Hostettmann K. New acetylcholinesterase inhibitors from Gentiana campestris L. 15 th International Symposium on Pharmaceutical and Biomedical Analysis, Florence, Italie, 2004. Urbain A., Marston A., Hostettmann K. Coumarins from Peucedanum ostruthium as inhibitors of acetylcholinesterase. International Congress and 53 rd Annual Meeting of the Society for Medicinal Plant Research, Florence, Italie, 2005. Di Giovanni S., Reist M., Borloz A., Urbain A., Marston A., Hostettmann K. Carrupt P.A. Comparison of two
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