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Page De Garde Faculté des Sciences de la Nature et de la Vie, des Sciences de la Terre et de l’Univers Département de Biologie Laboratoire des produits Naturels THÉSE Présentée par Mr TOUL Fethi Pour l’obtention du diplôme de Doctorat en Biologie Option : Biologie cellulaire et biochimie Profil polyphénolique et activité antioxydante des extraits des différents organes de Pistacia atlantica Desf. subsp. atlantica de la région de Tlemcen Soutenue le 15/03/2018, devant le jury composé de : Pr. DJAZIRI Rabah Président Univ.Tlemcen Pr. ATIK-BEKKARA Fawzia Directrice de thèse Univ.Tlemcen Dr. BELYAGOUBI- Co-directrice Univ.Tlemcen BENHAMMOU Nabila Examinatrice Pr. BELARBI Meriem Univ.Tlemcen Pr. BENMEHDI Hocine Examinateur Univ.Bechar Pr. DJEBLI Noureddine Examinateur Univ.Mostaganem Année Universitaire : 2017/2018 ‘‘La perfection n’est pas de ce monde. Ne sont parfaites que les intentions.’’ -proverbe arabe - DÉDICACES Au centre de gravité et à l’esprit de notre famille, mon cher grand -père . À celui qui a fait de ma réussite sa préoccupation majeure, mon honorable père . À celle qui m’a donné vie et ne cesse de m’en donner, ma précieuse mère . À celle qui partage ma vie et qui ne cesse de m’encourager, ma chère épouse . À celle qui m’apporte joie, à la fragrance de la maison, notre petite R AYHANA . À ceux qui m’épaulaient et qui m’épaulent toujours, mes chaleureux frère et sœurs À ma belle -famille , mes amis et tout le reste de ma famille . TOUL Fethi REMERCIEMENTS Je voudrais tout d'abord adresser toute ma gratitude au professeur ATIK- BEKKARA Fawzia , d’avoir accepté la direction de cette thèse, je tiens à lui exprimer ma profonde reconnaissance et ma gratitude pour sa disponibilité, sa patience, ses conseils, sa compréhension et ses qualités pédagogiques et scientifiques. Veuillez trouver ici, madame, ma reconnaissance et tout mon respect. Un spécial remerciement est adressé à Mme BELYAGOUBI-BENHAMMOU Nabila, maitre de conférences au département de Biologie, faculté des sciences de la nature et de la vie et des sciences de la terre et de l’univers, université Abou Bekr Belkaid Tlemcen , pour son aide scientifique et matérielle et ses conseils précieux, qu’elle trouve ici le témoignage de ma profonde reconnaissance. Je tiens à remercier Monsieur DJAZIRI Rabah , professeur au département de biologie, faculté des sciences de la nature et de la vie et des sciences de la terre et de l’univers, université Abou Bekr Belkaid Tlemcen, pour l’honneur qu’il m’a fait en acceptant de juger ce travail et de présider le jury. Je désire aussi remercier Madame BELARBI Meriem, Professeur au département de biologie, facultés des sciences de la nature et de la vie et des sciences de la terre et de l’univers, université Abou Bekr Belkaid Tlemcen, d’avoir accepté de lire et d’examiner ce travail, je tiens à lui transmettre tous mes sentiments d’estime et de respect que je lui dois. J’exprime également mes sincères remerciements à Mr. DJEBLI Noureddine , Professeur au département de Biologie, Université Abdelhamid IBN BADIS Mostaganem, d’avoir accepté d’examiner cette thèse, qu’il trouve ici l’expression de ma gratitude. Mes remerciements vont également à Mr. BENMEHDI Houcine , Professeur au département de Biologie, Université TAHRI Mohamed Bechar, pour m’avoir honoré d’être examinateur de ce travail. Je tiens à vous exprimer, Monsieur, ma sincère reconnaissance et mon plus profond respect. Je remercie aussi Mr. KOKKALOU Eugenius, professeur et chef du laboratoire de pharmacognosie au sein de la faculté de pharmacie à l’université d’Aristote de Thessalonique, Grèce, de m’avoir accueilli dans son laboratoire et d’avoir mis à ma disposition tout le matériel et le personnel du laboratoire, qu’il sache que je lui en suis très reconnaissant. Un remerciement particulier à Mme. MOUSSOUNI Sonia, Docteur en pharmacie à l’université d’Aristote de Thessalonique, Grèce, pour m’avoir gentiment apporté son aide qui m’était très précieux. Je vous adresse, madame, tout le respect et l’estime que je vous dois. Je remercie spécialement, Mme DJENDAR Amina , ma chère femme, pour son aide, pour sa patience et sa présence et pour son soutien permanent. Un remerciement fraternel et amical à Mme SELADJI Meryem , à Mme ZITOUNI Amel , à Mme GHEMBAZA Nacera , à Mme DIB Hanane et à Mr HACI Imad Abdelhamid, pour leurs aides scientifiques et leurs bonnes humeurs. Enfin j’adresse mes remerciements à tous ce qui ont participé à l’accomplissement de ce travail, de prés et de loin. Merci. رجاا /وع,+*()'&%$فإ"!ا فداتأة، وFاDEن9A6(Bةا@ت?>))ع,+<=>;:89،,7$،و56!34ا12ل، JK/ةاG Pistacia atlantica Desf. subsp atlantica GHIو?>38\[\=>ا2ر4ت ً اIا=>ا^jّ Jاi/وذe2,fg)8تا_,))ac`\داتا_)ل. %$فااإ"!@Hqاpطا2دnةlm;\mتا9A+@H@)k ;\wmأ6ءا3\اwذ/،وذE/2gأي7$أu)ىr\E>sا2دة nة، وFا qE اB m\4)6 ا\qت ?> }\">: اqرة cy ا2دة nة،@B/~@31{ا^Jرا^|/ u، DPPHرة@31{ا^|واqرة56!@31{@•€ ا•\}رو@Aن،إEإ"!اHq@H@ qE+\)ىا3\\داتا_)ل,4\ل @qت_. @Aن aل ا\i أن اm;\2 ا^م m:9اc ) H6ا ,\دات ا_)ل، ا_E)8)'ات،ا_E)8)توا\8•ت،أA84(\8&m;\/Fنأ:u9رةدة nة،B@<=`a/~@31{ا^Jرا^|/ DPPH و@B/~@31{@•€ا•\}رو@Aن, A9 دة)اmE\31{اIC50) •_l) 0.016 /و 0.006 /،,9@•™. 8/ا _ اm;\2 ا^م m:9اH6 ا2دة nة وﻩ ,\دات ا_)ل u ,\r\ijB,4\لا\qتا\:/و@)/اEاqIا/qu،/و @)/اEا )د و ا/و@)/اEاfز'وا4,)`)لإ"!/ms ا\+m اA8/, •_Iنا)وي اf2• ( £¢•&¡د ¥NMR -2D§ أcاp,6wا2/تاm6ml+@)k»$. ّ aلاا@ا6wأر•¬e)8ت و?>:إ£ن})ر' ،EE)8)ن و EE)ن. اتا : اHI ،\داتا_)ت،ا_ا2دةnة،ا/و@)/اE اfز'، ا/A8نا)وياf2• ( £¢•&¡د . Résumé Ce travail s’inscrit dans le cadre d’un programme de longue haleine visant à découvrir des antioxydants naturels. Plusieurs plantes font l’objet de nombreuses recherches dans notre laboratoire, nous citons l’espèce Pistacia atlantica Desf. subsp atlantica , une plante médicinale de la pharmacopée traditionnelle de l’Algérie, très riche en substances bioactives notamment les polyphénols. Le but de ce travail est d’évaluer l’activité antioxydante des extraits obtenus à partir des différents organes de P.atlantica afin de pouvoir connaitre celui ayant le pouvoir antioxydant le plus élevé, ceci a été fait par plusieurs techniques : la capacité antioxydante totale, DPPH *, Pouvoir de réduction du Fer et le test d’inhibition du blanchiment de β-carotène. En outre,les teneurs en polyphénols ont été mesurées par des techniques spectrophotométriques. L’extrait brut des bourgeons s’est révélé le plus riche en polyphénols totaux, en flavonoïdes, en flavonols et en tanins. L’extrait des anthocyanes de la même partie a montré l’activité antioxydante la plus importante, en comparaison avec l’antioxydant de référence (BHT), dans les deux tests de piégeage du radical libre DPPH *et d’inhibition du blanchiment de β-carotène, 16 µg/mL et 6µg/mL, respectivement. L’extrait brut des bourgeons, à cause de sa forte teneur en polyphénols et son importante activité antioxydante, a fait l’objet de plusieurs fractionnements successifs, par chromatographie sur couche mince, chromatographie sur colonne ouverte chromatographie CLHP-préparative. Ces fractionnements nous ont permis de passer à l’identification des fractions obtenues par RMN-2D. Ce travail nous a permis de mettre en évidence quatre molécules : la 7- ethoxycoumarine, 3',5,7-Trihydroxy-4'-methoxyflavanone, la 7-hydroxy-5- methoxycoumarine et la 5,6,7,4'-tetrahydroxyflavonol-3-O-rutinoside. Mots clés : Pistacia atlantica Desf. subsp atlantica , composés phénoliques, activité antioxydante, CLHP, RMN-2D. Abstract This work is a part of a long-term program, which aims to discover natural antioxidants. Several plants are the subject of several researches in our laboratory; we quote the species Pistacia atlantica Desf. subsp atlantica , a medicinal plant of the traditional pharmacopoeia of Algeria, very rich in bioactive substances including polyphenols. The aim of this work is to evaluate the antioxidant activity of the extracts obtained from the different organs of P.atlantica in order to know the one having the highest antioxidant power, this has been done by several techniques : total antioxidant capacity , DPPH * radical scavenging assay, Ferric Reducing Ability assay and β-carotene bleaching assay. In addition, polyphenol contents were measured by spectrophotometric techniques. The crude extract of buds was the richest extract in total polyphenols, flavonoids, flavonols and tanins. The anthocyanins extract of the same part showed the most important antioxidant activity, compared to reference (BHT), in DPPH * radical scavenging and β-carotene bleaching assays, 16 µg / mL and 6 µg / mL, respectively. Buds crude extract, because of its high content of polyphenols and its high antioxidant activity, has been subjected to several successive fractionations, by thin layer chromatography, open column chromatography, and preparative-HPLC. These fractionations allowed us to go on to identify the fractions obtained by NMR-2D. This work allowed us to identify four molecules: 7-ethoxycoumarin, 3 ', 5,7- Trihydroxy-4'-methoxyflavanone, 7-hydroxy-5-methoxycoumarin and 5,6,7,4'- Tetrahydroxyflavonol-3-O-rutinoside. Keywords : Pistacia atlantica Desf.subsp atlantica , phenolic compounds, antioxidant activity, HPLC, NMR-2D. TABLE DES MATIÈRES Dédicace Remerciements Résumé Abstract Table des matières Liste des figures Liste des photos Liste des tableaux Abréviations Introduction……………………………………………………………………… 1 Première partie : Synthése bibliographique CHAPITRE 1 : Description botanique, composition chimique et activités 3 biologiques de Pistacia atlantica Desf. subsp atlantica I- Généralités sur la plante étudiée………………………………………………. 3 I-1- Description botanique et systématique de Pistacia atlantica Desf…………. 3 I-2- Propriétés et usages thérapeutiques…………………………………………. 4 I-3- Travaux antérieurs…………………………………………………………... 5 CHAPITRE 2 : Les composés phénoliques, classification et activité 7 antioxydante I- Classification des composés phénoliques……………………………………..
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