Activity of extracts and naphthylisoquinoline alkaloids from Triphyophyllum peltatum, Ancistrocladus abbreviatus and A. Barteri against Plasmodium falciparum in vitro☆

François, Guido; Bringmann, Gerhard; Phillipson, J. David; Assi, Laurent Aké; Dochez, Carine; Rübenacker, Martin; Schneider, Christoph; Wéry, M; Warhurst, David C.; Kirby, G. C.

doi:10.1016/s0031-9422(00)86875-2

Cited by 57 publications

(38 citation statements)

References 16 publications

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“…Asexual erythrocytic stages of P. falciparum (NF 54, clone A1A9; FrancË ois et al 1994b) were continuously maintained following previously described methods (Trager and Jensen 1976;FrancË ois et al 1994a). Vismione H (1), the anthranoid compounds derived from Cortinarius spp., and those of synthetic origin were carefully dissolved in dimethylsulfoxide (DMSO) at a concentration of 0.05 mg/ll.…”

Section: Antiplasmodial Assaysmentioning

confidence: 99%

Vismione H and structurally related anthranoid compounds of natural and synthetic origin as promising drugs against the human malaria parasite Plasmodium falciparum : structure-activity relationships

François

Steenackers

Assi

et al. 1999

Parasitology Research

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Natural and synthetic anthranoid compounds were subjected to an evaluation against asexual erythrocytic stages of the human malaria parasite Plasmodium falciparum in vitro. Stimulated by the good activities of Vismia guineënsis extracts, a more detailed investigation of the active principles revealed the pre-nylated preanthraquinone vismione H (1) to be a potent antimalarial [50% growth-inhibitory concentration (IC50) 0.088 microg/ml]. On the basis of this finding a series of chemically related phlegmacins (2-5), flavomannins (6-8), and rufoolivacins (9-11) isolated from several species of Cortinarius, a genus of higher fungi, and 5 synthetic vismione-like anthranoids (12-16) were evaluated as well. Although these compounds displayed weaker antiplasmodial effects than did vismione H (1) itself, considerable levels of activity were obtained with phlegmacin B1 (2), flavomannin-6,6'-di-O-methyl ether A1 (6), trans-4-hydroxy-flavomannin-6,6'-di-O-methyl ether A (8), and rufoolivacin B (10). Initial preconditions for activity within the vismiones and related anthranoids were established.

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Section: Antiplasmodial Assaysmentioning

confidence: 99%

Vismione H and structurally related anthranoid compounds of natural and synthetic origin as promising drugs against the human malaria parasite Plasmodium falciparum : structure-activity relationships

François

Steenackers

Assi

et al. 1999

Parasitology Research

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“…In a rodent model (OF1 mice infected with P. berghei), intravenous administration of dioncophylline C (median effective dose ED 50 ¼ 1.90 mg kg À1 day À1 ) and dioncopeltine A (ED 50 ¼ 10.71 mg kg À1 day À1 ) achieved a complete clearance of parasites from the circulation of P. berghei-infected mice (François et al 1997a(François et al , 1997b. Their mode of action seems to be similar to that of chloroquine, inhibiting the degradation of toxic haem metabolites in the food vacuole of the malaria parasite (François et al 1999); on the other hand, these compounds are also highly active against chloroquine resistant strains (François et al 1994).…”

Section: Introductionmentioning

confidence: 96%

Biotransformation and pharmacokinetics of the antiplasmodial naphthylisoquinoline alkaloid dioncophylline A

Sieber¹,

Dekant²,

Faber

et al. 2006

Xenobiotica

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The biotransformation of the antiplasmodial naphthylisoquinoline alkaloid dioncophylline A by rat liver microsomes and its pharmacokinetics in male rats were studied. Incubation of dioncophylline A with rat liver microsomes resulted in the formation of the major metabolite 5'-O-demethyldioncophylline A, and a second minor metabolite, corresponding to the mass of an as yet unknown 4-hydroxydioncophylline A. Kinetic constants of the formation of 5'-O-demethyldioncophylline A were Km = 32 nmol and Vmax = 20 pmol min-1 mg-1). Administration of dioncophylline A at a dose of 6.67 mg kg-1 body weight to rats intravenously and orally (n = 4 per group) resulted in peak plasma levels of 0.84 and 0.11 microg ml-1, respectively. Levels of metabolites were below the limit of quantitation (LOQ). The following pharmacokinetic parameters of dioncophylline A were determined: oral bioavailability of 25%, plasma half-life of 2.5 h and partition volume of 8 l kg-1 body weight. Concentrations of dioncophylline A metabolites in all plasma and urine samples were below the limit of detection (LOD) and recovery of dioncophylline A in urine was very low, suggesting distribution into lipid rich tissues.

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“…These alkaloids showed in vitro activity against the K1 (multi drug resistant) and NF54 (CQ sensitive) strains of P. falciparum [11], as well as P. berghei [12]. Experimental studies showed that dioncopeltine A (4) was able to suppress parasitemia almost totally, while dioncophylline C (7, ED 50 =10.71mg/kg/day) cured P. berghei infected mice completely after oral treatment (50mg/kg/day for four days).…”

Section: Isoquinoline Alkaloidsmentioning

confidence: 99%

Perspective in Antimalarial Chemotherapy

Kumar¹,

Katiyar²,

Agarwal³

et al. 2003

CMC

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Antimalarial chemotherapy has become more complex and challenging because of multidrug resistant strains of Plasmodium falciparum. Due to resistance of malarial parasite against well known drugs, the chemotherapy of malaria has become complicated. In this review we have discussed brief introduction followed by life cycle of malaria parasite. The list of commercially available antimalarial drugs along with there action on different stages of parasite have been discussed. A brief description of their mechanism of action and advantages and disadvantages were reported. The natural products as antimalarial have been discussed in the review. On the basis of chemical classes the natural products were divided in the following categories; Quinoline alkaloids, Iso-quinoline alkaloids, Indoloquinoline alkaloids, Carbolines, Bis-isoquinoline, 4-Quinazole derivatives, Trioxanes, Terpenes, Naphthoquinone, Anthraquinones, Chalcones, Hydroxy flavanones, Coumarins and phenolic glycoside. The combination chemotherapy has been highlighted in the review. The Biochemical and Immunological changes in malarial infection are discussed along with complications of malarial chemotherapy due to resistance. In the conclusion section, the future strategies for the chemotherapy of malaria have been discussed.

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Activity of extracts and naphthylisoquinoline alkaloids from Triphyophyllum peltatum, Ancistrocladus abbreviatus and A. Barteri against Plasmodium falciparum in vitro☆

Cited by 57 publications

References 16 publications

Vismione H and structurally related anthranoid compounds of natural and synthetic origin as promising drugs against the human malaria parasite Plasmodium falciparum : structure-activity relationships

Vismione H and structurally related anthranoid compounds of natural and synthetic origin as promising drugs against the human malaria parasite Plasmodium falciparum : structure-activity relationships

Biotransformation and pharmacokinetics of the antiplasmodial naphthylisoquinoline alkaloid dioncophylline A

Perspective in Antimalarial Chemotherapy

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