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Chimie Des Substances Naturelles Et De Biomolécules

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Chimie Des Substances Naturelles Et De Biomolécules UNIVERSITÉ BLIDA 1 Faculté des sciences Département de Chimie THÈSE DE DOCTORAT LMD Spécialité : Chimie des substances naturelles et de biomolécules ÉTUDE CHIMIQUE DES MÉTABOLITES (PRIMAIRES ET SECONDAIRES) PRODUITS PAR DES SOUCHES BACTÉRIENNES ISSUES DE NICHES ECOLOGIQUES MARINES Par HAMICHE Sonia Devant le jury composé de : Z. DJAZOULI Professeur, Université Saad Dahlab Blida 1 Président H. BOUTOUMI Professeur, Université Saad Dahlab Blida 1 Examinateur S. AKKAL Professeur, Université Constantine 1 Examinateur A. ZITOUNI Professeur, Ecole Normale Superieure Kouba Examinateur M. EL HATTAB Professeur, Université Saad Dahlab Blida 1 Directeur de thèse A. BADIS Professeur, Université Saad Dahlab Blida 1 Codirecteur de thèse Blida, 11 Janvier 2020 ملخص يتمحور هذا العمل حول الدراسة الكيميائية و تقييم اﻷنشطة المضادة لﻷكسدة للمشتقات الفينولية من الطحلب البني Zonaria tournefortii، العزل والوصف المظهري للسﻻﻻت البكتيرية المرتبطة بنفس الطحلب وتثمين البكتريا المعزولة في إنتاج المركبات ذات اﻷهمية الحيوية، البيئية و الصناعية. سمحت الدراسة الكيميائية للمستخلص الدهني للطحلب بعزل المركبات الفينولية المشتقة من الفلوروغلوسينول، وعلى وجه الخصوص اﻷسيلفلوروغلوسينول، وقد أظهر تقييم اﻷنشطة المضادة لﻷكسدة للمركبات المعزولة، أن جميع المركبات لها نشاط مضاد لﻷكسدة. من جهة أخرى، سمح الوصف اﻷولي لثﻻثين سﻻلة بكتيرية معزولة من Zonaria tournefortii وهذا بإتباع مقاربة مظهرية مبنية على أساس الدراسات المورفولوجية، البيوكيميائية واﻷيضية بالحاق العزﻻت إلى اﻷجناس Staphylococcus )14عزلة(، Bacillus )12عزلة( و Acinetobacter )عزلتان(، والى عائلة البكتيريا المعوية )عزلتان(. مكنت دراسة قابلية السﻻﻻت البكتيرية ﻹنتاج المركبات الطيارة والمنتشرة المضادة للميكروبات وكذا اﻹنزيمات المحللة للكيراتين، من إختيار السﻻلة اﻷكثر كفاءة والمسماة بـ S13، والتي نسبت إلى النوع Bacillus amyloliquefaciens باﻻعتماد على تحديد تتابع النيكليوتيدات للمورثة المشفرة للـ ARN الريبوزومي 16S. تم إنتاج المركبات المضادة للميكروبات بحضن السﻻلة S13 في الوسط المغذي LB المضاف إليه الـ NaCl بتركيز 51‰ لمدة 84 ساعة في حرارة 03 درجة وحموضة ابتدائية 7,2. تنتمي أهم المركبات الطيارة والمنتشرة المحددة، على التوالي، بتقنية CG/SM وCL/ESI-SMHR إلى التربينات الثنائية من نوع Labdane والبيبتيدات الحلقية من عائلة DKP( dicétopipérazines-5,1(. تم إجراء إنتاج لﻹنزيمات المحللة للكيراتين بعد 24 ساعة من حضن السﻻلة البكتيرية عند 03 درجة في وسط مح سن بقاعدة مسحوق ريش الدجاج. كشف التحليل بواسطة تقنية طيف الكتلة أن للجزيئتين اﻹنزيميتين KERTZ-A وKERTZ-B، الكتلة 28 و47 كيلو دالتون على التوالي .أظهرالتوصيف الكيميائي الحيوي لﻹنزيمين أن النشاط المثالي بالنسبة لـKERZT-A كان في معامل الحموضة 6,5 ودرجة الحرارة °50 مئوية. أما KERZT-B فقد ُس ِّ جل نشاطها المثالي على درجة حرارة °60 مئوية بمعامل حموض 8. هذه الخصائص الكيميوحيوية الملحوظة للجزيئتين اﻹنزيميتين يمكن أن تفتح فر ًصا واعدة جديدة ﻹعادة تدوير البقايا الكيراتينية والحد من تأثيرها على البيئة. الكلمات المفتاحية: Bacillus amyloliquefaciens S13 ،Zonaria tourneforii، acylphloroglucinols، النشاط المضاد لﻷكسدة، التربينات الثنائية, 2,5-dicétopipérazines، اﻹنزيمات المحللة للكيراتين. RÉSUMÉ Le présent travail porte sur l’étude chimique et l’investigation des activités antioxydantes des dérivés phénoliques de l’algue brune Zonaria tournefortii, l’isolement et la caractérisation préliminaire de la communauté bactérienne associée à l’algue, et la valorisation des bactéries isolées dans la production des métabolites d’intérêt bioactif, environnemental et industriel. L’étude chimique de l’extrait lipidique de l’algue a permis l’isolement des produits phénoliques dérivés du phloroglucinol en particulier les acylphloroglucinols, et l’évaluation des activités antioxydantes des produits isolés a montré que tous les composés présentent une activité antioxydante potentielle. La caractérisation préliminaire de trente souches bactériennes isolées de Zonaria tournefortii en utilisant une approche phénotypique basée sur des études morphologiques, biochimiques et métaboliques a permis de rattacher les isolats aux genres Staphyloccocus (14 isolats), Bacillus (12 isolats) et Acinetobacter (2 isolats), et à la famille des Entérobacteraceae (2 isolats). L'étude des potentialités des souches bactériennes isolées dans la production des composés antimicrobiens volatils et diffusibles ainsi que des enzymes kératinolytiques a permis de sélectionner une souche plus performante codée S13, affiliée à l'espèce Bacillus amyloliquefaciens via le séquençage du gène codant de l’ARNr 16S. La production de métabolites antimicrobiens a été effectuée après une culture de la souche à 30 °C pendant 48 h dans un milieu LB additionné de 15 ‰ NaCl, avec un pH initial de 7,2. Les principaux composés volatils et diffusibles identifiés, respectivement, par CG/SM et CL/ESI-SMHR, appartiennent aux diterpènes de types Labdane et aux dipeptides cycliques de la famille de 2,5-dicétopipérazines (DKP). La production des kératinases a été effectuée après 42h de culture de la souche à 30 °C dans un milieu optimisé à base de farine de plume de poulet. L’analyse SDS/PAGE des deux kératinases purifiées (KERZT-A et B), révèle qu’il s’agit d’un seul monomère ayant une taille estimée à 28 kDa pour KERZT-A et 47 kDa pour KERZT-B. La caractérisation biochimique des deux enzymes a montré que les valeurs optimales de pH et de température sont de 6,5, 50 °C, et 8, 60°C pour KERZT-A et KERZT-B, respectivement. Les propriétés biochimiques remarquables des deux enzymes, pourrait ouvrir de nouvelles opportunités prometteuses pour la valorisation des déchets kératinolytiques et la réduction de ses impacts sur l’environnement. Mots clés : Zonaria tournefortii, Bacillus amyloliquefaciens S13, acylphloroglucinols, activité antioxydante, diterpenes, 2,5-dicétopipérazines, kératoinases. ABSTRACT The present work focuses on the chemical study and the investigation of the antioxidant activity of phenolic derivatives of the brown algae Zonaria tournfortii, the isolation and phenotypic characterization of the bacterial community associated with the alga and the valorization of the isolated bacteria in the production of metabolites with bioactive, environmental and industrial interest. The chemical study of the lipidic extract of the algae allowed the isolation of phenolic compounds derived from phloroglucinol, in particular acylphloroglucinol. The evaluation of the antioxidant activity of the isolated compounds showed that all compounds had a potential antioxidant effect. The preliminary characterization of 30 bacterial strains isolated from Zonaria tournefortii by a phenotypic approach based on morphological, biochemical and metabolic studies allowed to attach the isolates to the genders Staphyloccocus (14 isolates), Bacillus (12 isolates) and Acinetobacter (2 isolates) and to the Enterobacteriaceae family (2 isolates). The study of the potential of the isolated bacterial strains on the production of volatile and diffusible antimicrobial compounds as well as keratinolytic enzymes allowed the selection of the most efficient strain encoded S13, affiliated to Bacillus amyloliquefaciens by sequencing the 16S rRNA gene. The production of antimicrobial metabolites was performed after incubation of the selected strain on Luria–Bertani medium with NaCl 15‰ (w/v), pH 7.2 at 30°C for 48 h. The main volatile and diffusible compounds were identified by GC/MS and LC/ESI- HRMS. They belong to Labdane-type diterpenes and cyclic dipeptides class of 2,5- diketopiperazines (DKP) family. The production of keratinases was performed after 42h of incubation of the selected strain at 30°C in an optimized medium based on chicken feather meal. The SDS/PAGE analysis of the two purified keratinases (KERZT-A and B), revealed that it is a single monomer with an estimated size of 28 kDa for KERZT-A and 47 kDa for KERZT-B. The biochemical characterization of the two enzymes showed that the optimum pH and temperature values were 6.5, 50°C, and 8, 60°C for KERZT-A and KERZT-B, respectively. The remarkably biochemical properties of the two enzymes could open a new promising opportunities for the recovery of keratinolytic waste and the reduction of its impact on the environment. Key words: Zonaria tournefortii, Bacillus amyloliquefaciens S13, acylphloroglucinols, antioxidant activity, diterpenes, 2,5-diketopiperazines, keratinases. REMERCIEMENTS En tout premier lieu, je remercie le bon Dieu, tout puissant, de m’avoir orienté vers la lumière de la recherche de la science et du savoir et de m’avoir donné la force pour dépasser toutes les difficultés. Mes plus sincères remerciements vont à mes très chers parents que dieu protège, qui ont su croire en moi et qui ont m’avoir soutenue tout au long de mes études. Merci pour votre amour, votre aide et confiance et surtout pour votre présence dans les moments difficiles et de déprime. En témoignage de ma profonde affection, qu’ils sachent que ce travail est en grande partie le fruit de leur soutien; je leur suis très reconnaissante. Leur fierté à mon égard aujourd’hui est pour moi la meilleure des récompenses. Je témoigne ici ma profonde gratitude à mes directeurs de thèse, Professeur El Hattab Mohamed et Professeur Badis Abdelmalek, qui ont accepté de prendre la direction de cette thèse, transformant ainsi les difficultés rencontrées en une expérience enrichissante. Je tiens à leur remercier de m’avoir confiée ce sujet de thèse pluridisciplinaire entre la chimie et la microbiologie. Je leur suis également reconnaissante de m’avoir assuré un encadrement rigoureux tout au long de ces années, tout en me donnant la possibilité de trouver par moi même mon cheminement personnel et, de m’avoir témoigné de la confiance en m’accordant une grande autonomie dans ce
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