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, Guido; Steenackers, Tania; Assi, Laurent Aké; Steglich, Wölfgang; Lamottke, Kai; Holenz, Jörg; Bringmann, Gerhard

doi:10.1007/s004360050598

Cited by 34 publications

(38 citation statements)

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“…0.23 mM. From these prior results, it appears that multiple prenylations are not the only requirements for strong anti-plasmodial activity, as was demonstrated by the potency of Vismione H. 25) The two triterpenoids (6, 7) evaluated in this work displayed moderate activities (IC 50 s of 7.7 mM and 5.1 mM respectively). Betulinic acid has already been evaluated for antiplasmodial activity in a previous work.…”

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confidence: 54%

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Anti-plasmodial Activity of Some Constituents of the Root Bark of Harungana madagascariensis LAM. (Hypericaceae)

et al. 2007

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Malaria remains the one of the most important infectious diseases in the world. It constitutes a public health problem in more than 90 countries, inhabited by about 40% of the world's population. The World Health Organisation estimates that there are 300-500 million malaria cases annually, causing 2-3 million deaths, mostly in children under five years old.1) Africa accounts for over 90% of malaria mortality. 1)Malaria also has significant economic impacts in endemic countries, costing Africa $ 12 billon in lost gross domestic product every year and consuming 40% of all public health spending.2) Most countries where Plasmodium falciparum malaria, the most severe and dangerous form of this disease, is endemic face significant parasite resistance to frequently used antimalarial drugs, in particular chloroquine and antifolates. Furthermore, resistance to artemisinins, which are the most promising new antimalarials, has been induced in rodent malarial models 3) and identified rarely in clinical isolates. If resistance to artemisinins emerges, no drug will be available to reliably offer protection against malaria in all parts in the world and the efficacy of new artemisinin-based combination therapies (ACTs), which are highly effective, but expensive, will be jeopardized. For these reasons, new effective and affordable antimalarials are badly needed. 4) In this regard research on traditional medicinal plants for their antimalarial constituents is important, to facilitate utilization of available botanical resources and to provide potentially active lead anti-plasmodial compounds, perhaps with new mechanisms of action. In Africa, the use of indigenous plants still plays an important role in the treatment of malaria. 5,6) Some anthrone derivatives from plant sources have demonstrated interesting anti-plasmodial activity. 7,8) They are also naturally occurring competive inhibitors of adenosinetriphosphate-citrate-lyase. 9) Plants of the Hypericaceae family are well known to produce bioactive anthraquinones and anthrones. They are distributed in tropical and sub-tropical regions.10) Harungana madagascariensis, a plant from this family, is used for various medicinal purposes in Africa. 11,12) Leaf extract of this plant exhibited antibacterial activity. 13) In the West province of Cameroon, the roots and bark are used by traditional healers to treat malaria. Various phenolic compounds have been isolated from this plant, among them anthraquinones, xanthones, biflavonoids, coumarins and anthrone derivatives.14-16) These compounds have demonstrated a wide range of biological activities. [16][17][18] Although some phytochemical and pharmacological studies have been carried out on H. madagascariensis, no investigation has been reported, to the best of our knowledge, on the anti-plasmodial activity of its constituents. In our continuing interest in new anti-plasmodial metabolites from plant sources, we investigated the MeOH-CH 2 Cl 2 (1 : 1) root bark extract of this plant which showed anti-plasmodial activity (IC 50 ϭ25.12 mg/m...

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“…25) Of note, Vismione H isolated from Vismia guineensis was found to be very active in vitro against P. falciparum (NF 54, clone A1A9), with an IC 50 of ca. 0.23 mM.…”

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Anti-plasmodial Activity of Some Constituents of the Root Bark of Harungana madagascariensis LAM. (Hypericaceae)

et al. 2007

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“…A literature study of these species revealed that only seven species, Alstonia bonei (Gandhi and Vinayak, 1990;Wright et al, 1993), Abrus precatorius (Limmatvapirat et al, 2004), Cassia occidentalis (Addae- Kyereme et al, 2001;Gasquet et al, 1993;Tona et al, 1999;Tona et al, 2001), Momordica charantia (Amorim et al, 1991;Munoz et al, 2000;Ueno et al, 1996), Nauclea latifolia (Azas et al, 2002;Benoit-Vical et al, 1998), Vernonia colorata (Benoit et al, 1996) and Vismia guineensis (Francois et al, 1999), had previously been investigated for antiplasmodial activity. To our knowledge, this is the first time that Annona muricata, Cola caricaefolia, Canna indica, Desmodium adscendens, Erigeron floribundus, Hoslundia opposita, Mitragyna ciliata, Olax subscorpioidea, Parkia biglobosa, Parketina nigrescens and Uvaria afzelii are being assessed for their antiplasmodial properties.…”

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confidence: 97%

Antiplasmodial activity and cytotoxicity of plants used in West African traditional medicine for the treatment of malaria

Menan

Banzouzi

Hocquette

et al. 2006

Journal of Ethnopharmacology

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“…Several prenylated anthranoids have also been reported with respect to their anti-plasmodial activity. 26) The isolated anthranoids are derivatives of emodin 13. Compounds 5, 6, and 10 with anthracene-9,10-dione skeleton were less active than the anthrones 2, 4 or bianthrones 1 and 12.…”

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Anti-plasmodial and Cholinesterase Inhibiting Activities of some Constituents of Psorospermum glaberrimum

et al. 2008

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Malaria is still the most devastating parasitic disease in the world, causing 2-3 million deaths every year, mostly among children under five years old and pregnant women. Africa accounts for over 90% of malaria mortality. 1) In the last decades resistance of Plasmodium falciparum, the causative agent of the most severe form of the disease, to several antimalarials, especially chloroquine and antifolates, became widely disseminated, while the cost of effective treatment is prohibitive for the large majority of the populations. For these reasons, new effective and affordable antimalarials are urgently needed.2) In Africa and elsewhere, the use of indigenous plants plays an important role in malaria treatment. 3)These plants are indeed an interesting source of new antiplasmodial compounds perhaps with new mechanisms of action.Psorospermum glaberrimum HOCHR. (Hypericaceae) is a small-to medium-sized shrub (up to 3 m high) distributed in tropical regions. Leaves and bark extracts of this plant are used in traditional medicine for the treatment of several diseases across Africa.4) The decoctions of leaves and bark are used to treat epilepsy, respiratory affections and external uses for skin diseases and leprosy. The extracts of the root bark are used for the treatment of severe cases of malaria. The pulped roots and bark extracts and the bark red resin powdered with dried leaves are remedies used externally for skin diseases and leprosy. The boiled bark gives a soapy product that is mixed with oil to rub on the skin or applied to sores for animals to keep away flies that cause scabies.4) Previous phytochemical investigations of Psorospermum species reported the presence of bioactive xanthones, anthraquinones, vismiones and psorolactones.5-16) Although some phytochemical studies have been carried out on P. glaberrimum, to the best of our knowledge, no investigation has been reported on its anti-plasmodial activity and inhibitory properties towards acetyl-and butyrylcholinesterase (AChE and BChE). AChE and BChE have been identified as attractive targets in the treatment of Alzheimer's dementia, myasthenia gravis, glaucoma, and in the recovery of victims of nerve agent exposure. Any chemical that inhibits cholinesterase activity increases the availability of acetylcholine to sustain nerve cell communications.17) Hence, cholinesterase inhibitors act as potential leads in drug discovery for nervous-system disorders.In our continuing interest in new bioactive metabolites from Cameroonian medicinal plants, we investigated the hexane extract of stem bark of P. glaberrimum which showed potent anti-plasmodial activity against the W2 strain of P. falciparum, and good AChE and BChE inhibition in vitro. In this paper, we report on the isolation and structure elucidation of a new bianthrone derivative 1, the 13 C-NMR data of the known bianthrone A2b (11) together with the anti-plasmodial and cholinesterase inhibiting activities of the isolated compounds. Results and DiscussionThe air dried stem bark of P. glaberrimum was extracted...

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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

Cited by 34 publications

References 25 publications

Anti-plasmodial Activity of Some Constituents of the Root Bark of Harungana madagascariensis LAM. (Hypericaceae)

Anti-plasmodial Activity of Some Constituents of the Root Bark of Harungana madagascariensis LAM. (Hypericaceae)

Antiplasmodial activity and cytotoxicity of plants used in West African traditional medicine for the treatment of malaria

Anti-plasmodial and Cholinesterase Inhibiting Activities of some Constituents of Psorospermum glaberrimum

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