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Page De Garde ار اا اا ا وزارة ا ا و ا ا République Algérienne Démocratique et Populaire Ministère de l’Enseignement Supérieur et de la Recherche Scientifique Université d’Oran Es-Sénia Faculté des Sciences Département de Biologie Mémoire en vue de l’obtention du diplôme de Magistère en Biologie Option : Biochimie Végétale Appliquée Thème Screening de plantes pour leur activité inhibitrice de l’acétylcholinestérase et analyse phytochimique Présenté par : Mr BENAMAR Houari Soutenu le 2008, devant la commission du jury : Mr BELKHODJA Moulay Prof. Université d’Oran Président Mr AOUES Abdelkader Prof. Université d’Oran Examinateur Mme BENNACEUR Malika M.C. Université d’Oran Examinatrice Mr MAROUF Abderrazak M.C. Université d’Oran Rapporteur 2008-2009 REMERCIMENTS Ce travail a été réalisé au Laboratoire de Biochimie Végétale (Département de Biologie, Faculté des Sciences, Université d’Oran, Es-Sénia), sous la direction du Docteur MAROUF Abderrazak (Maître de conférences à l’Université d’Oran, Es-Sénia), à qui j’exprime mes sincères remerciements pour ses connaissances, sa compétence, sa rigueur scientifique et ses conseils avisés. Mes très vifs remerciements vont à Monsieur BELKHODJA Moulay, Professeur à l’Université d’Oran, Es-Sénia, d'avoir accepté la présidence du jury de ce mémoire. Mes chaleureux remerciements vont aussi à Monsieur AOUES Abdelkader, Professeur à l’Université d’Oran, Es-Sénia, d’avoir accepté d’examiner ce travail. J'exprime ma profonde gratitude à Madame BENNACEUR Malika, Maître de conférences à l’Université d’Oran, Es-Sénia, d'avoir accepté d’examiner ce travail et de nous avoir aidé tout au long du magister, qu'elle trouve ici le témoignage de mon profond remerciement. Mes remerciements vont à tous mes camarades du magister : Amine, Fatiha, Fatima, Nawel et Wahiba, pour leur encouragement et leur gentillesse. Mes profonds remerciements vont aussi à nos techniciens du laboratoire Belkhir, Faïza, Saliha, à Khalida (LBMB), Amina (Laboratoire d’Ecopédologie) et Souad (Laboratoire de Botanique), qu’ils acceptent l’expression de mon entière reconnaissance. Je tiens à adresser un hommage à la mémoire de Madame KHOUAÏJIA Malika, enseignante à l’Université d’Oran, Es-Senia. DÉDICACE le tous puissant qui m’a donné le courage et la volonté pour ,« ﺍﷲ » C’est grâce à Dieu achever ce modeste travail que je dédie : A mes très chers parents en reconnaissance de leurs divers sacrifices, de leurs précieux conseils, de leur soutien moral et de leurs encouragements tout au long de mes études et durant ce mémoire. Je ne les remercierai jamais assez, pour tout ce qu'ils m'ont fait. A mon chère oncle Karim qui ma donné l'aide et le courage à surmonter les situations pénibles. A mes deux chers frères. A mes très chères sœurs. A mes amis Hmed, Miloud, Mohammed et Mustafa. A ceux qui ont contribué de prés ou de loin à l’élaboration de ce travail. Houari RESUME L’inhibition de l’acétylcholinestérase (AChE, EC 3.1.1.7), enzyme clé dans le clivage de l’acétylcholine, est considérée comme une stratégie prometteuse pour le traitement des maladies neurodégénératives telle que la maladie d’Alzheimer. Dans ce contexte, l’objectif de cette étude consiste à réaliser un screening de l’activité inhibitrice de l’AChE de certaines plantes médicinales ainsi que leur profil phytochimique. La bioautographie sur couche mince a révélé 10 extraits aqueux actifs sur un total de 77 extraits évalués à une quantité de 13,3 µg. Parmi lesquels l’extrait aqueux de Pistacia lentiscus L. a présenté sept spots actifs dont un est de nature flavonoïdique. La méthode colorimétrique d’Ellman a montré que l’extrait aqueux de Pistacia atlantica Desf et de Pistacia lentiscus L. présente une très forte inhibition de l’AChE, par contre l’extrait aqueux de Rosmarinus officinalis L. a montré la plus faible inhibition. Les valeurs d’IC 50 obtenues pour ces trois extraits sont 0,87 ± 0,55 - 13,67 ± 0,69 - 207,41 ± 10,04 µg/mL respectivement. La fraction chloroformique issue du partage liquide- liquide de l’extrait aqueux des racines d’ Atriplex halimus L. a montré la plus forte inhibition de l’AChE parmi toutes les fractions testées avec une IC 50 de 9,55 ± 2,91 µg/mL. Le screening phytochimique par CCM a révélé que Globularia alypum L. et Osyris quadripartita Salzm. sont très riches en métabolites secondaires. Le dosage quantitatif des flavonoïdes et des polyphénols totaux par méthode colorimétrique a permis de qualifier Osyris quadripartita Salzm. et Pistacia atlantica Desf comme étant les plus riches en composés phénoliques (438,99 ± 7,52 - 407,68 ± 9,23 mg/g), par contre Rosmarinus officinalis L. et Acacia raddiana Savi ont montré la teneur la plus élevée en flavonoïdes (125,70 ± 11,33 - 115,37 ± 11,28 mg/g). Mots clés : Inhibition de l’acétylcholinestérase ; Maladie d’Alzheimer ; Plantes médicinales ; Bioautographie ; Métabolites secondaires. iii ABSTRACT Inhibition of acetylcholinesterase (AChE, EC 3.1.1.7), the key enzyme in the breakdown of acetylcholine, is considered as a promising strategy for the treatment of neurological disorders such as Alzheimer’s disease. In this context, the aim of this study consists to realise a screening of some medicinal plants for acetylcholinesterase inhibitory activity and their phytochemical profile. The bioautography on Thin-layer chromatography (TLC) reveals 10 active aqueous extracts for a total of 77 extracts evaluated at a quantity of 13,3 µg. Among it, aqueous extract of Pistacia lentiscus L. presents seven active spots, one of them is identified as flavonoid. The Ellman’s colorimetric method showed that aqueous extract of Pistacia atlantica Desf and Pistacia lentiscus L. present a strong AChE inhibition, contrary the aqueous extract of Rosmarinus officinalis L. showed weak inhibition. The IC 50 values obtained for these extracts were 0,87 ± 0,55 - 13,67 ± 0,69 - 207,41 ± 10,04 µg/mL respectively. The chloroformic fraction obtained after partition of Atriplex halimus L. roots aqueous extract, showed a strong AChE inhibition among all fractions tested with IC 50 of 9,55 ± 2,91 µg/mL. The phytochimical screening by TLC revealed that Globularia alypum L. and Osyris quadripartita Salzm. contains several secondary metabolites. The quantitative dosage of flavonoids and total polyphenols by colorimetric method showed that Osyris quadripartita Salzm. and Pistacia atlantica Desf are the richest on total phenolic compounds (438,99 ± 7,52 - 407,68 ± 9,23 mg/g), contrary Rosmarinus officinalis L. and Acacia raddiana Savi presents highest content on flavonoids (125,70 ± 11,33 - 115,37 ± 11,28 mg/g). Key words : Acetylcholinesterase inhibition ; Alzheimer’s disease ; medicinal plants ; Bioautography ; Secondary metabolites. iv ABRÉVIATIONS A : Asymmetric collagen-tailed forms a : Amphiphilique AcCoA : Acétyl-Coenzyme A ACh : Acétylcholine AChE : Acétylcholinestérase AcOEt : Acétate d’éthyle AcOH : Acide acétique AlCl 3 : Chlorure d’aluminium AMM : Autorisation de Mise sur le Marché AMPc : Adénosine monophosphate cyclique ATChI : Acétylthiocholine iodide BChE : Butyrylcholinestérase BSA : Bovine serum albumine ChAT : Choline-acétyl-transférase CBM : Carbamates CCM : Chromatographie sur couche mince Ch : Choline CH 2Cl 2 : Dichlorométhane CHCl 3 : Chloroforme ChEs : Cholinestérases CoA : Coenzyme A ColQ : Collagène Q DAG : Diacylglycérol DFP : Diisopropylphosphonofluoridate DO : Densité optique DTNB : 5,5'-dithiobisnitrobenzoate EtOH : Ethanol FCS : Fluide cérébrospinal FDA : Food and Drug Administration G : Globulaire Gal : Galanthamine GPI : Glycophosphatidylinositol HCl : Chlorure d’hydrogène HCOOH : Acide formique HPLC : Chromatographie liquide haute performance IC 50 : Concentration nécessaire pour inhiber 50 % de l’activité enzymatique Ins(1.4.5)P3 : Inositol-1.4.5-trisphosphate Iso-OMPA : Tetraisopropylpyrophosphoramide Kcat : Constante catalytique Km : Constante de Michaelis KOH : Hydroxyde de potassium LBD : Lewy Bodies Dementia MA : Maladie d’Alzheimer MéOH : Méthanol MS : Spectroscopie de masse na : Non-amphiphilique Na 2CO 3 : Bicarbonate de sodium v Na 2HPO 4 : Phosphate disodique NaH 2PO 4 : Phosphate monosodique NaNO 2 : Nitrate de sodium NaOH : Hydroxyde de sodium n-BuOH : n-Buthanol NH 4OH : Hydroxyde d’ammoniaque OP : Organophosphorés P : Degré de signification PEG : Polyéthylène glycole PKC : Protéine kinase Ca 2+ dépendante PRiMA : Récepteur membranaire riche en proline R2 : Cœfficient de corrélation Rf : Facteur de rétention s : seconde SbCl 3 : Chlorure d’antimoine TcAChE : Torpedo californica Acétylcholinestérase UV : Ultraviolet v : vitesse δ : Facteur de dilution vi LISTE DES FIGURES Figure 1 : Photographie d’ Acacia raddiana Savi. 7 Figure 2 : Photographie d’ Atriplex halimus L. 9 Figure 3 : Photographie de Globularia alypum L. 12 Figure 4 : Photographie de Myrtus nivellei Batt & Trab. 15 Figure 5 : Photographie d’ Olea lapperini Batt & Trab. 17 Figure 6 : Photographie d’ Osyris quadripartita Salzm. 19 Figure 7 : Photographie de Pistacia atlantica Desf. 21 Figure 8 : Photographie de Pistacia lentiscus L. 23 Figure 9 : Photographie de Rhus pentaphylla L. 26 Figure 10 : Photographie de Rosmarinus officinalis L. 28 Figure 11 : Photographie de Tetraclinis articulata (Vahl.) Masters. 31 Figure 12 : Synthèse de l’ACh. 37 Figure 13 : Synapse cholinergique. 38 Figure 14 : Hydrolyse de l’ACh par l’AChE. 39 Figure 15 : Vue détaillée du site actif de la Tc AChE. 40 Figure 16 : Structure tridimensionnelle de la Tc AChE. 41 Figure 17 : Structure tridimensionnelle de l’AChE. 41 Figure 18 : Vue détaillée du site périphérique de la Tc
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