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Search for Antiplasmodial Compounds from Ghanaian Medicinal Plants Gustav Komlaga

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Search for Antiplasmodial Compounds from Ghanaian Medicinal Plants Gustav Komlaga Search for antiplasmodial compounds from Ghanaian medicinal plants Gustav Komlaga To cite this version: Gustav Komlaga. Search for antiplasmodial compounds from Ghanaian medicinal plants. Parasitol- ogy. Université Paris-Saclay; Kwane Nkrumah University of Science and Technology (Ghana), 2015. English. NNT : 2015SACLS265. tel-01340366 HAL Id: tel-01340366 https://tel.archives-ouvertes.fr/tel-01340366 Submitted on 1 Jul 2016 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. NNT : 2015SACLS265 THÈSE DE DOCTORAT DE L’UNIVERSITÉ PARIS-SACLAY PRÉPARÉE À UNIVERSITÉ PARIS-SUD ECOLE DOCTORALE N° 569 Innovation thérapeutique : du fondamental à l'appliqué Spécialité de doctorat: Microbiologie Par M. Gustav Komlaga Titre de la thèse Search for antiplasmodial compounds from Ghanaian medicinal plants [Recherche de composés antiplasmodiaux de plantes médicinales Ghanéennes] Thèse présentée et soutenue à KNUST, Ghana, le 15 Décembre 2015 Composition du Jury : M. Abaidoo, C. Robert Professor à KNUST Président M. Mensah, L. K. Merlin Professor à KNUST Rapporteur Mme. Appiah-Opong, Regina Dr à University of Ghana, Legon Examinatrice M. Champy, Pierre Professor à Université Paris-Sud Examinateur M. Arthur, K. Patrick Dr à University of Ghana, Legon Examinateur M. Adu, Joseph Dr à KNUST Examinateur M. Loiseau, M. Philippe Professor à Université Paris-Sud Directeur de thèse Mme. Dickson, A. Rita. Dr à KNUST Co-directeur de thèse Titre : titre (en français) : Recherche de composés antiplasmodiaux de plantes médicinales Ghanéennes Mots clés : Phyllanthus fraternus, Bambusa vulgaris, composés antiplasmodiale, paludisme, alcaloïdes de type sécurinegar, allo-norsercurinine. 3-oxo-α-ionol. Résumé: Au Ghana, de nombreuses plantes successives (éther de pétrole, acétate d’éthyle, médicinales sont utilisées dans le traitement du méthanol), à partir de matériaux de 5 plantes, paludisme ou d’autres pathologies. Une recherche de sélectionnées en raison de leur importance dans le molécules antiplasmodiales a donc été entreprise à traitement traditionnel du paludisme et d’un manque partir de plantes employées localement dans le de données appropriées dans la littérature. Ces traitement de la maladie. Une enquête plantes sont: Phyllanthus fraternus (plante entière); ethnobotanique a d’abord été réalisée, dans deux Tectona grandis (feuille); Terminalia ivorensis régions ghanéennes, Bosomtwi et Sekyere East, afin (feuille), Bambusa vulgaris (feuille) et Senna siamea d’identifier les plantes utilisées, comparativement à (racine). L’évaluation a été réalisée sur les souches celles employées comme ingrédients de produits 3D7 (i.e. chloroquine-sensible) et W2 (i.e. manufacturés antimalariques à base de plantes. chloroquine-résistante) de Plasmodium falciparum. L’enquête a permis l’inventaire de 98 espèces Tous les extraits aqueux ont montré une intéressante végétales : douze (12; 12.2%) sont identifiées pour activité antiplasmodiale, avec des CI50 inférieures à la première fois dans cette indication thérapeutique ; 10 µg/mL, à l’exception de S. siamea, peu actif vingt (20; 20.4%) sont rapportées pour la première contre 3D7 P. falciparum. Seulement les extraits de fois au Ghana. D’autre part, vingt-trois (23) produits T. ivorensis et S. siamea ont montré une activité manufacturés et étiquetés, constitués d’une ou contre W2 P. falciparum (CI50 <50 µg / ml). Leurs plusieurs plantes réputées antimalariques, ont été indices de sélectivité (SI) étaient supérieurs à 3,5, et relevés : ils contiennent les parties aériennes ou leurs indices de résistance (RI) inférieurs à 20. Les souterraines de vingt-neuf des plantes de fractions organiques ont été tout aussi actif (IC50 l’inventaire. Vingt-deux (22) de ces produits sont <50 µg / mL; 3D7 de P. falciparum). Les extraits enregistrés par la FDA du Ghana, quatre (4) étant méthanoliques se sont montrés les plus actifs, inclus dans la liste des médicaments à base de notamment les extraits de P. fraternus et B. vulgaris plantes pour le traitement du paludisme conseillé par (CI50 < 1 µg/mL), qui ont été fractionnés par des le service de santé du Ghana. Un criblage techniques chromatographiques usuelles, visant à préliminaire d’activité antiplasmodiale a été réalisé purifier les molécules actives et à élucider leurs sur les extraits traditionnels aqueux ainsi que sur des structures. L’étude de P. fraternus a permis extraits organiques obtenus par extractions l’obtention de 6 composés, Pf1 à Pf6, identifiés ii comme étant la phyllanthine (un lignane) et 5 le déhydrovomifoliol ou [(E)-4-hydroxy-3,5,5- alcaloïdes de type sécurinine, inconnus dans cette trimethyl-4-(3-oxobut-1-en-1-yl)cyclohex-2-en-1- espèce : la nirurine, la norsecurinine, l’allo- one]; le 3-oxo-α-ionol ou 9-hydroxyméga norsecurinine, isolée pour la première fois d’une stigma-4, 7-dièn-3-one; le loliolide ou 6-hydroxy-4, source naturelle, la bubbialine, isolée pour la 4, 7a-trimethyl-5, 6, 7, 7a-tetrahy- première fois d’un Phyllanthus, et l’epibubbialine. drobenzofuran-2(4H)-one et la tricine ou 5, 7,4'- Ces composés ont montré des activités trihydroxy-3',5'-dimethoxyflavone. Aucun n’était antiplasmodiales significatives contre les deux connu dans l’espèce. Tous ont montré une activité souches (CI50 : 1.14 ± 0.32 µM à 59.00 ± 5.43 µM), antiplasmodiale in vitro, sur les souches 3D7 (CI50 < montrée pour la première fois pour cette classe 5 µM) et W2 (CI50 < 7 µM), les plus actifs contre d’alcaloïdes. La norsecurinine était la plus active chacune des souches étant l’acide p-coumarique (souche W2). D’autre part, seules la nirurine et la (CI50: 0.84 ± 0.90 µM ; 3D7) et l’acide cinnamique phyllanthine ont montré une cytotoxicité sur cellules (CI50: 1.41 ± 0.38 µM ; W2). Cette activité n’avait HUVEC (CC50 < 100 µM). L’étude chimique de jamais été observée pour chacune des molécules l’extrait méthanolique de B. vulgaris a également obtenues à partir de la plante. Cette étude illustre le permis d’isoler 6 molécules, Bv1 à Bv6, identifiées potentiel de la flore Ghanéenne. comme étant les acides p-coumarique et cinnamique; iii Title : Titre (en anglais) : Search for antiplasmodial compounds from Ghanaian medicinal plants. Keywords : Phyllanthus fraternus, Bambusa vulgaris, antiplasmodial compound, malaria, securinega alkaloids, allo-norsecurinine, 3-oxo-α-ionol Abstract : In Ghana, many medicinal plants are used materials included the whole of Phyllanthus in the treatment of malaria and other diseases. A fraternus, leaves of Tectona grandis, Terminalia search for antiplasmodial compounds was carried ivorensis and Bambusa vulgaris, and root of Senna out on plants traditionally employed to treat malaria. siamea. All the aqueous extracts showed notable An ethnobotanical survey was performed in the antiplasmodial activity (IC50 < 10 µg/mL), except Bosomtwi and Sekyere East Districts of Ghana to that of S. siamea, against 3D7 P. falciparum. Only T. identify plants used locally to manage malaria. This ivorensis and S. siamea extracts showed activity was done in comparison with the plant ingredients in against W2 P. falciparum (IC50 < 50 µg/mL). The marketed herbal antimalarial remedies in the Kumasi extracts demonstrated high selectivity index (SI) for metropolis. The survey inventoried ninety-eight (98) 3D7 P. falciparum (SI > 3.5) but very low SI for W2 plant species; twelve (12; 12.2%) reported for the P. falciparum. Resistance index (RI) was largely first time globally, and twenty (20; 20.4%) others for under 20. The organic fractions were equally active the first time in Ghana for the treatment of malaria. (IC50 < 50 µg/mL; 3D7 P. falciparum). The Twenty-three (23) locally available finished, often methanol extracts of the two most potent plant multi/polyherbal antimalarial products examined materials, the whole of P. fraternus and leaf of B. contained aerial or underground parts of twenty-nine vulgaris, were subjected to phytochemical study to (29) of the plants cited in the survey as ingredients. isolate and elucidate the chemical constituents, Twenty-two (22) of these products were registered which were then assayed for antiplasmodial activity. by the Ghana Food and Drugs Authority; four (4) The phytochemical study of the methanol extract of were included in the Ghana Health Service P. fraternus yielded six compounds; Pf 1 to Pf 6 recommended herbal medicine list for treating identified as the lignan, phyllanthin, and five malaria in Ghana. The aqueous as well as serially securinega alkaloids namely nirurine, ent- extracted organic solvents (petroleum ether, ethyl norsecurinine, allo-norsecurinine, bubbialine and acetate, and methanol) extracts of five plants parts, epibubbialine. This is the first isolation of allo - selected based on their importance in the traditional norsecurinine from a natural source and bubbialine treatment of malaria and lack of the appropriate data from the Phyllanthus genus. The compounds in the literature, were studied against the displayed significant antiplasmodial activity against chloroquine-sensitive 3D7 and chloroquine-resistant both 3D7 and W2 P. falciparum (1.14 ± 0.32 µM ≤ W2 P. falciparum parasite in vitro. The plant IC50 ≤ 59.00 ± 5.43 µM); ent-norsecurinine being iv the most active (IC50=1.14± 0.32 µM) and against compounds from B. vulgaris displayed significant the W2 P. falciparum. Only Pf2 (nirurine) and Pf1 activity against 3D7 (IC50 < 5 μM and W2 strains of (phyllanthin) displayed cytotoxicity (CC50 < 100 P. falciparum (IC50 < 7 μM). Bv1 (p-coumaric acid) µM; HUVECs). This is the first report of the was the most active against 3D7 P. falciparum antiplasmodial activity of these compounds. Similar (IC50: 0.84 ± 0.90 μM) and Bv2 (cinnamic acid) the study of the methanol extract of B.
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