References of "Frederich, Michel"
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See detailDécouverte de substances naturelles antipaludiques et métabolomique.
Frederich, Michel ULg

Scientific conference (2012, May 16)

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See detailPotential anticancer activity of young Carpinus betulus leaves.
Cieckiewicz, Ewa ULg; Angenot, Luc ULg; Gras, T. et al

in Phytomedicine : International Journal of Phytotherapy and Phytopharmacology (2012), 19(3/4), 278-284

As part of our continuing research for anticancer compounds from the Walloon Region forest, EtOAc extract from Carpinus betulus leaves was phytochemically studied, leading to the bioguided isolation of ... [more ▼]

As part of our continuing research for anticancer compounds from the Walloon Region forest, EtOAc extract from Carpinus betulus leaves was phytochemically studied, leading to the bioguided isolation of pheophorbide a, which is responsible of anticancer properties of C. betulus young leaves. This compound was identified using nuclear magnetic resonance and mass spectrophotometric data and comparison with a commercial standard. Evaluation of the growth inhibitory activities of pheophorbide a using MTT colorimetric assay and phase-contrast microscopy in various human cancer cell lines confirmed the photoactivable properties of this compound. Our research showed, for the first time, the presence of pheophorbide a, a chlorophyll derived compound, which we quantified in high quantities in young leaves of C. betulus. This is in contrast with the literature which generally describes pheophorbide a as a catabolic product of chlorophyll, then preferentially present in old leaves. [less ▲]

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See detailAlkaloids from the stem bark of Strychnos icaja
Tchinda Tiabou, Alembert ULg; Tamze, Victorine; Ngono, Annie R N et al

in Phytochemistry Letters (2012), 5(1), 108-113

A comprehensive phytochemical study of the stem bark of Strychnos icaja was done for the first time and led to the isolation of two new monoindole alkaloids 15-hydroxyvomicine (1) and 12-methoxyicajine (2 ... [more ▼]

A comprehensive phytochemical study of the stem bark of Strychnos icaja was done for the first time and led to the isolation of two new monoindole alkaloids 15-hydroxyvomicine (1) and 12-methoxyicajine (2) along with 13 known alkaloids: the monoindoles N-methyl-sec-iso-pseudostrychnine (3), vomicine (4), icajine (5), 19,20-α-epoxy-12-methoxyicajine (6), 19,20-α-epoxy-12,15-dihydroxy-11-methoxyicajine (7), 19,20-α-epoxy-15-hydroxynovacine (8), 15-hydroxyicajine (9), 12-hydroxystrychnine (10), strychnine (11) and the tertiary bisindoles sungucine (12), isosungucine (13), strychnogucine C (14) and bisnordihydrotoxiferine (15). Apart from 10 and 11, the other alkaloids were isolated for the first time from the stem bark of this plant. The hemisynthetic derivative, Nb-chloromethosungucine (16) and the previously reported synthetic compound 3 were isolated from a natural source for the first time. Fractions and some isolated compounds were tested against the chloroquine-sensitive 3D7 strain of Plasmodium falciparum. The bisindole alkaloids were most active with IC50 ranging from 0.72 to 3.41 μg/ml whilst the monomers 1 and 3 were slightly active (IC50 39.92 and 40.27 μg/ml respectively) and 6 inactive. The structures of the compounds were determined based on the analysis of their spectral data. The full 1H and 13C NMR data of compounds 3, 6 and 7 are also reported in the present work for the first time. [less ▲]

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See detailCombination of capillary electrophoresis, molecular modelling and nuclear magnetic resonance to study the interaction mechanisms between single-isomer anionic cyclodextrin derivatives and basic drug enantiomers in a methanolic background electrolyte.
Servais, Anne-Catherine ULg; Rousseau, Anne; Dive, Georges ULg et al

in Journal of Chromatography. A (2012), 1232

In order to improve our knowledge of the mechanisms of enantiomer recognition pattern in nonaqueous systems, an approach combining nonaqueous CE (NACE), molecular modelling and NMR was undertaken ... [more ▼]

In order to improve our knowledge of the mechanisms of enantiomer recognition pattern in nonaqueous systems, an approach combining nonaqueous CE (NACE), molecular modelling and NMR was undertaken. Bupivacaine and propranolol were selected as model compounds and their interactions with two single-isomer highly charged beta-CD derivatives, namely heptakis(2,3-di-O-methyl-6-O-sulfo)-beta-CD (HDMS-beta-CD) and heptakis(2,3-di-O-acetyl-6-O-sulfo)-beta-CD (HDAS-beta-CD), were studied. The CD-bupivacaine complexes were evaluated by 2-D Rotating-frame Overhauser Effect SpectroscopY (ROESY) experiments. From these experiments, it can be assumed that inclusion complexes are not formed, whatever the CD derivative used. Molecular modelling was performed at the RHF/MINI-1 or B3LYP/6-31G(d) level. External as well as inclusion type complexes with the alkyl chain of propranolol into both CD cavities were located. Interaction energies calculated for bupivacaine and propranolol correlated with the enantiomer migration order observed in the NACE experiments using both anionic CD derivatives. The interaction of propranolol with HDMS-beta-CD or HDAS-beta-CD gives rise to a family of external and inclusion complexes in which some are more probably obtained. [less ▲]

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See detailAnti-plasmodial activity of Dicoma tomentosa (Asteraceae) and identification of urospermal A-15- O-acetate as the main active compound.
Jansen, Olivia ULg; Tits, Monique ULg; Angenot, Luc ULg et al

in Malaria Journal (2012), 11(1), 2891-9

ABSTRACT: BACKGROUND: Natural products could play an important role in the challenge to discover new anti-malarial drugs. In a previous study, Dicoma tomentosa (Asteraceae) was selected for its promising ... [more ▼]

ABSTRACT: BACKGROUND: Natural products could play an important role in the challenge to discover new anti-malarial drugs. In a previous study, Dicoma tomentosa (Asteraceae) was selected for its promising anti-plasmodial activity after a preliminary screening of several plants traditionally used in Burkina Faso to treat malaria. The aim of the present study was to further investigate the antiplasmodial properties of this plant and to isolate the active anti-plasmodial compounds. METHODS: Eight crude extracts obtained from D. tomentosa whole plant were tested in vitro against two Plasmodium falciparum strains (3D7 and W2) using the p-LDH assay (colorimetric method). The Peters' four-days suppressive test model (Plasmodium berghei-infected mice) was used to evaluate the in vivo anti-plasmodial activity. An in vitro bioguided fractionation was undertaken on a dichloromethane extract, using preparative HPLC and TLC techniques. The identity of the pure compound was assessed using UV, MS and NMR spectroscopic analysis. In vitro cytotoxicity against WI38 human fibroblasts (WST-1 assay) and haemolytic activity were also evaluated for extracts and pure compounds in order to check selectivity. RESULTS: The best in vitro anti-plasmodial results were obtained with the dichloromethane, diethylether, ethylacetate and methanol extracts, which exhibited a high activity (IC50 [less than or equal to] 5 mug/ml). Hot water and hydroethanolic extracts also showed a good activity (IC50 [less than or equal to] 15 mug/ml), which confirmed the traditional use and the promising anti-malarial potential of the plant. The activity was also confirmed in vivo for all tested extracts. However, most of the active extracts also exhibited cytotoxic activity, but no extract was found to display any haemolytic activity. The bioguided fractionation process allowed to isolate and identify a sesquiterpene lactone (urospermal A-15-O-acetate) as the major anti-plasmodial compound of the plant (IC50 < 1 mug/ml against both 3D7 and W2 strains). This was also found to be the main cytotoxic compound (SI =3.3). While this melampolide has already been described in the plant, this paper is the first report on the biological properties of this compound. CONCLUSIONS: The present study highlighted the very promising anti-plasmodial activity of D. tomentosa and enabled to identify its main active compound, urospermal A-15-O-acetate. The high antiplasmodial activity of this compound merits further study about its anti-plasmodial mechanism of action. The active extracts of D. tomentosa, as well as urospermal A 15-Oacetate, displayed only a moderate selectivity, and further studies are needed to assess the safety of the use of the plant by the local population. [less ▲]

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See detailArdisikivuoside, a new triterpenoid saponin from Ardisia kivuensis (Mysinaceae)
Ndontsa, Blanche; Tchinda Tiabou, Alembert ULg; Teponno, Rémy et al

in Natural Product Communications [=NPC] (2012), 7

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See detailRotenoid content and in vitro acaricidal activity of Tephrosia vogelii leaf extract on the tick Rhipicephalus appendiculatus
Kalume; Losson, Bertrand ULg; Angenot, Luc ULg et al

in Veterinary Parasitology (2012), 190(1-2), 204-209

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See detailPolyphenol Content and Modulatory Activities of Some Tropical Dietary Plant Extracts on the Oxidant Activities of Neutrophils and Myeloperoxidase
Tsumbu, César Ndele ULg; Deby-Dupont, Ginette; Tits, Monique ULg et al

in International Journal of Molecular Sciences (2012), 13(1), 628-650

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See detailUNDERSTANDING THE INTERACTIONS BETWEEN ARTEMISININ AND CYCLODEXTRINS: SPECTROSCOPIC STUDIES AND MOLECULAR MODELING
Zime Diawara, Hermine; Dive, Georges ULg; Piel, Géraldine ULg et al

in Journal of Inclusion Phenomena and Molecular Recognition in Chemistry (2012), 74(1), 305-315

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See detailLC–SPE–NMR–MS analysis of Strychnos usambarensis fruits from Rwanda
Cao, Martine ULg; Muganga, Raymond; Nistor, Iolanda ULg et al

in Phytochemistry Letters (2012), 5(0), 170-173

The novelty of the present work lies in the characterization of akagerine and palicoside in Strychnos usambarensis fruits by a hyphenated analytical method combining high-performance liquid chromatography ... [more ▼]

The novelty of the present work lies in the characterization of akagerine and palicoside in Strychnos usambarensis fruits by a hyphenated analytical method combining high-performance liquid chromatography coupled with solid-phase extraction (SPE), mass spectrometry (HPLC–MS) and NMR spectroscopy. Akagerine was already known in S. usambarensis roots but palicoside is described for the first time in the species. [less ▲]

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See detailAntiparasitic activities of two sesquiterpenic lactones isolated from Acanthospermum hispidum D.C
Ganfon; Bero, Joanne; Tchinda Tiabou, Alembert ULg et al

in Journal of Ethnopharmacology (2012), 141(0), 411-417

Ethnopharmacological relevance : Aerial parts of Acanthospermum hispidum D.C. are often used by traditional healers in Benin for various diseases and especially for malaria Aim of the study : Identify ... [more ▼]

Ethnopharmacological relevance : Aerial parts of Acanthospermum hispidum D.C. are often used by traditional healers in Benin for various diseases and especially for malaria Aim of the study : Identify active compounds from extracts of Acanthospermum hispidum D.CV. leaves previously shown to possess antimalarial properties and analyse in vivo activity and toxicity of crude extracts. Materials and methods : Compounds were isolated from aerial part of A. hispidum D.C. and structurally elucidated using extensive spectroscopic analysis. Antiplasmodial activity was evaluated in vitro against a chloroquinosensitive strain of Plasmodium falciparum (3D7) using the measurement of the plasmodial lactate dehydrogenase activity and in vivo against P. berghei berghei by the 4-days suppressive test. Selectivity of extract and purified compounds on Plasmodium parasites were evaluated by using MTT test on J774 macrophage like murine cells and WI38 human normal fibroblasts and also against two other parasites: Trypanosoma brucei brucei and Leishmania mexicana mexicana. Acute and sub-acute toxicities of a crude extract were evaluated on mice. Results : Two known sesquiterpenic lactones were isolated: 1 (15-acetoxy-8β-[(2-methylbutyryloxy)]-14-oxo-4, 5-cis-acanthospermolide) and 2 (9α-acetoxy-15-hydroxy-8β-(2-methylbutyryloxy) -14-oxo-4, 5-trans-acanthospermolide). 1 and 2 showed in vitro antiplasmodial activity against the chloroquino-sensitive strain (3D7) with IC50 of 2.9 ± 0.5 and 2.23 ± 0.09 μM respectively. Only 2 showed a high selectivity index (SI: 18.4) on Plasmodium compared to cytotoxicity against human fibroblasts cell line (WI38). 1 and 2 also showed interesting antiparasitic activities in vitro against Trypanosoma brucei brucei (IC50 of 2.45 ± 0.49 and 6.36 ± 1.42 μM respectively) and Leishmania mexicana mexicana (IC50 of 0.94 ± 0.05 and 2.54 ± 0.19 μM respectively). Furthermore, crude acidic water extract and fractions containing one of the two isolated compounds displayed a weak in vivo antimalarial activity against P. berghei berghei with a long half-life causing a delayed effect. In vivo acute (2000 mg/kg) and sub-acute (1000 mg/kg) toxicity tests on the crude acidic water extract did not show toxicity. Conclusion : Crude acidic water extract, fractions and pure isolated compounds from A.hispidum showed promising in vitro antiplasmodial activity. Despite our study did not show in vivo acute and subacute toxicities of the crude acidic water extract, its weak in vivo antimalarial activity and the in vitro cytoxicity of pure compounds and enriched extracts containing 1 and 2 indicate that the aerial parts of A. hispidum should be used with caution for malaria treatments. [less ▲]

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See detailAntiplasmodial Alkaloids from the Stem Bark of Strychnos malacoclados.
Tchinda Tiabou, Alembert ULg; Ngono, A. R.; Tamze, V. et al

in Planta Medica (2012), 78

From the stem bark of STRYCHNOS MALACOCLADOS, one new bisindole alkaloid, 3-hydroxylongicaudatine Y ( 1), was isolated along with the known alkaloids vomicine ( 2), bisnordihydrotoxiferine ( 3), divarine ... [more ▼]

From the stem bark of STRYCHNOS MALACOCLADOS, one new bisindole alkaloid, 3-hydroxylongicaudatine Y ( 1), was isolated along with the known alkaloids vomicine ( 2), bisnordihydrotoxiferine ( 3), divarine ( 4), longicaudatine ( 5), longicaudatine Y ( 6), and longicaudatine F ( 7). All the compounds were tested for their antimalarial activity against the chloroquine-sensitive 3D7 and -resistant W2 strains of PLASMODIUM FALCIPARUM. Longicaudatine was the most active compound with IC (50) values of 0.682 and 0.573 microM, respectively. The activity of compounds 1, 3, 4, 6, and 7 against the two strains ranged from 1.191 to 6.220 microM and 0.573 to 21.848 microM, respectively. Vomicine ( 2), the only monomer isolated, was inactive. The alkaloids of the longicaudatine-type ( 1, 5- 7) were more active than those of the caracurine-type ( 3- 4). The presence of the ether bridge in the molecule seems to increase the antiplasmodial activity. Compounds 1, 5, and 7 were tested against the WI-38 human fibroblast cell line. Longicaudatine was the most cytotoxic compound with an IC (50) of 2.721 microM. Longicaudatine F was 40-46 times more active against the two strains of P. FALCIPARUM than against the human fibroblasts and was thus considered as the more selective alkaloid. The structures of the compounds were determined based on the analysis of their spectral data. [less ▲]

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See detailPhenolic Compounds and Terpenoids from Hypericum lanceolatum
Wabo, H. K.; Kowa, T. K.; Lonfouo, A. H. et al

in Records of Natural Products (2012), 6(2), 94-100

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See detail17-O-Actetyl-10-hydroxycorynantheol, a selective antiplasmodial alkaloid isolated from Strychnos usambarensis leaves
Cao, Martine ULg; Muganga, Raymond ULg; Tits, Monique ULg et al

Conference (2011, December 13)

In the course of our investigations on Strychnos usambarensis leaves in order to isolate isostrychnopentamine, the main alkaloid responsible for the antiplasmodial activity of the plant, a new tertiary ... [more ▼]

In the course of our investigations on Strychnos usambarensis leaves in order to isolate isostrychnopentamine, the main alkaloid responsible for the antiplasmodial activity of the plant, a new tertiary indolic alkaloid has been isolated: 17-O-acetyl, 10-hydroxycorynantheol 1. Its structure was determined by means of spectroscopic and spectrometric methods such as UV, IR, CD, NMR and ESI-MS. 17-O-acetyl, 10-hydroxycorynantheol 1 is one of the most active monomeric indole alkaloid known to date showing an in vitro activity against Plasmodium falciparum close to 5 µM and a high selectivity. [less ▲]

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See detail17-O-Acetyl,10-hydroxycorynantheol, a Selective Antiplasmodial Alkaloid Isolated from Strychnos usambarensis Leaves
Cao, Martine ULg; Muganga, Raymond ULg; Tits, Monique ULg et al

in Planta Medica (2011), 77

In the course of our investigations on Strychnos usambarensis leaves in order to isolate isostrychnopentamine, the main alkaloid responsible for the antiplasmodial activity of the plant, a new tertiary ... [more ▼]

In the course of our investigations on Strychnos usambarensis leaves in order to isolate isostrychnopentamine, the main alkaloid responsible for the antiplasmodial activity of the plant, a new tertiary indolic alkaloid has been isolated: 17-O-acetyl, 10-hydroxycorynantheol 1. Its structure was determined by means of spectroscopic and spectrometric methods such as UV, IR, CD, NMR and ESI-MS. 17-O-acetyl, 10-hydroxycorynantheol 1 is one of the most active monomeric indole alkaloid known to date showing an in vitro activity against Plasmodium falciparum close to 5 µM and a high selectivity. [less ▲]

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See detailIntroduction à la métabolomique
Frederich, Michel ULg

Conference (2011, May 18)

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See detail17-O-acetyl, 10-hydroxycorynantheol, a selective antiplasmodial alkaloid isolated from Strychnos usambarensis leaves
Cao, Martine ULg; Muganga, Raymond ULg; Tits, Monique ULg et al

Conference (2011, May 13)

In the course of our investigations on Strychnos usambarensis leaves in order to isolate isostrychnopentamine, the main alkaloid responsible for the antiplasmodial activity of the plant, a new tertiary ... [more ▼]

In the course of our investigations on Strychnos usambarensis leaves in order to isolate isostrychnopentamine, the main alkaloid responsible for the antiplasmodial activity of the plant, a new tertiary indolic alkaloid has been isolated: 17-O-acetyl, 10-hydroxycorynantheol 1. Its structure was determined by means of spectroscopic and spectrometric methods such as UV, IR, CD, NMR and ESI-MS. 17-O-acetyl, 10-hydroxycorynantheol 1 is one of the most active monomeric indole alkaloid known to date showing an in vitro activity against Plasmodium falciparum close to 5 µM and a high selectivity. [less ▲]

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See detailEspectroscopia aplicada
Ziemons, Eric ULg; Frederich, Michel ULg; Fillet, Marianne ULg et al

Scientific conference (2011, May)

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