Aporphine alkaloids from Enantia chlorantha

Wafo, Pascal; Nyasse, Barthélémy; Fontaine, C.; Sondengam, B.L.

doi:10.1016/s0367-326x(99)00016-7

Cited by 25 publications

(25 citation statements)

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“…The stembark extract of E. polycarpa showed high n vtro antiplasmodial activity against P. falcparum K1 strain (IC 50 0.126 µg/ml) and high selectivity (SI 616) (Atindehou et al, 2004). The chemistry of E. chlorantha and E. polycarpa has been extensively studied (Leboeuf & Cave, 1972;Jössang et al, 1977a, b;Wafo et al, 1999). The stem-bark and the leaves of E. chlorantha and E. polycarpa contain many biologically active alkaloids that are closely related.…”

Section: Introductionmentioning

confidence: 99%

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Antiplasmodial, anti-trypanosomal, anti-leishmanial and cytotoxicity activity of selected Tanzanian medicinal plants

Malebo¹,

Tanja²,

Cal³

et al. 2010

Tanzania J Hlth Res

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The antiplasmodial, anti-trypanosomal and anti-leishmanial activity of 25 plant extracts obtained from seven Tanzanian medicinal plants: Anncka (Enanta) kummerae (Annonaceae), Artemsa annua (Asteraceae), Pseudospondas mcrocarpa (Anacardiaceae), Drypetes natalenss (Euphorbiaceae), Acrdocarpus chloropterus (Malpighiaceae), Maytenus senegalenss (Celastraceae) and Neurautanena mts (Papilonaceae), were evaluated n vtro against Plasmodum falcparum K1, Trypanosoma bruce rhodesense STIB 900 and axenic Leshmana donovan MHOM-ET-67/82. Out of the 25 extracts tested, 17 showed good antiplasmodial activity (IC 50 0.04-5.0 µg/ml), 7 exhibited moderate anti-trypanosomal activity (IC 50 2.3-2.8 µg/ml), while 5 displayed mild anti-leishmanial activity (IC 50 8.8-9.79 µg/ml). A. kummerae, A. annua, P. mcrocarpa, D. natalenss, M. senegalenss and N. mts extracts had good antiplasmodial activity (IC 50 0.04-2.1 µg/ml) and selectivity indices (29.2-2,250 µg/ml). The high antiplasmodial, moderate anti-trypanosomal and mild anti-leishmanial activity make these plants good candidates for bioassay-guided isolation of anti-protozoal compounds which could serve as new lead structures for drug development.

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Section: Introductionmentioning

confidence: 99%

“…For instance Enanta chlorantha is used for the treament of malaria in West Africa (Wafo et al, 1999). Enanta chlorantha exhibited n vvo activity against Plasmodum yoel in experimentally infected mice (Agbaje & Onabanjo, 1991).…”

Section: Introductionmentioning

confidence: 99%

Antiplasmodial, anti-trypanosomal, anti-leishmanial and cytotoxicity activity of selected Tanzanian medicinal plants

Malebo¹,

Tanja²,

Cal³

et al. 2010

Tanzania J Hlth Res

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“…To our knowledge, an aporphine alkaloid with similar structural feature was isolated from the stem bark of Enantia chlorantha, and identified as 6a,7-dehydro-1,2-dimethoxy-7-hydroxyaporphine. 19 It shares 6a,7-dehydro-1,2-dimethoxy-aporphine skeleton, whereas it has hydroxyl group at C-7 and saturation at C-4/C-5.…”

Section: Resultsmentioning

confidence: 99%

Alkaloids from Acorus gramineus rhizomes and their biological activity

Kang

Eom

et al. 2015

Planta Med

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Como parte de nossa pesquisa em andamento por constituintes bioativos de fontes medicinais coreanas, um fracionamento biomonitorado e uma investigação química de extrato metanólico de rizomas de Acorus gramineus resultaram no isolamento e identificação de dois alcaloides, incluindo um novo alcaloide do tipo aporfina, chamado gramichunosina e um alcaloide pirrol conhecido. Suas estruturas foram determinadas por uma combinação de análises espectroscópicas de ressonância magnética nuclear (NMR) 1D e 2D e espectrometria de massas de alta resolução (HRMS). Este é o primeiro relato de alcaloides de A. gramineus. Os compostos isolados apresentaram atividade antiproliferativa contra as linhagens de células A549, SK-OV-3, SK-MEL-2, e HCT-15 com EC 50 na faixa de 7,46-45,23 μM. Ademais, as atividades antineuroinflamatórias desses compostos foram determinadas através da medida dos níveis de óxido nítrico (NO) meio utilizando células de microglia murina BV-2. O composto gramichunosina inibiu a produção de NO em células BV-2 estimuladas com lipopolisacarídeo com valores de IC 50 de 7,83 μM.As part of our ongoing search for bioactive constituents from natural Korean medicinal resources, a bioassay-guided fractionation and a chemical investigation of the methanolic extract from the rhizomes of Acorus gramineus resulted in the isolation and identification of two alkaloids, including a new aporphine-type alkaloid, named gramichunosin, and a known pyrrole alkaloid. Their structures were determined by a combination of 1D and 2D nuclear magnetic resonance (NMR) spectroscopic analysis and high resolution mass spectrometry (HRMS). This is the first report of alkaloids from A. gramineus. The compounds isolated showed antiproliferative activities against A549, SK-OV-3, SK-MEL-2 and HCT-15 cell lines with EC 50 values in the range of 7.46-45.23 μM. Moreover, the anti-neuroinflammatory activities of these compounds were determined by measuring the nitric oxide (NO) levels in the medium using murine microglia BV-2 cells. Compound named gramichunosin inhibited NO production in lipopolysaccharide-stimulated BV-2 with IC 50 values of 7.83 μM.

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“…Enantia chlorantha and E. polycarpa are used traditionally in the treatment of malaria and fever in West and Central Africa [9,10]. Consequently, previous pharmacological investigations on genus Enantia revealed promising anti-protozoal activity with the stem-bark extract of E. chlorantha showing strong in vitro anti-plasmodial activity against P. falciparum K1 strain (IC 50 0.126 μg/ml) and good selectivity (SI 616) [11].…”

Section: Introductionmentioning

confidence: 99%

“…chlorantha aqueous and ethanolic extracts exhibited in vivo activity with ED 50 values of 6.9 mg g-1 and 0.34 mg g-1, respectively, against Plasmodium yoelii in experimentally infected mice [12]. The chemistry of E. chlorantha and E. polycarpa has been extensively studied [10,13-15]. Several quinoline and isoquinoline alkaloids including protoberberines, quinine and dihydroquinidine have been isolated from E. polycarpa [16,17].…”

Section: Introductionmentioning

confidence: 99%

Anti-protozoal activity of aporphine and protoberberine alkaloids from Annickia kummeriae (Engl. & Diels) Setten & Maas (Annonaceae)

Malebo

Wenzler

Cal

et al. 2013

BMC Complement Altern Med

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BackgroundMalaria, trypanosomiasis and leishmaniasis have an overwhelming impact in the poorest countries in the world due to their prevalence, virulence and drug resistance ability. Currently, there is inadequate armory of drugs for the treatment of malaria, trypanosomiasis and leishmaniasis. This underscores the continuing need for the discovery and development of new anti-protozoal drugs. Consequently, there is an urgent need for research aimed at the discovery and development of new effective and safe anti-plasmodial, anti-trypanosomal and anti-leishmanial drugs.MethodsBioassay-guided chromatographic fractionation was employed for the isolation and purification of antiprotozoal alkaloids.ResultsThe methanol extract from the leaves of Annickia kummeriae from Tanzania exhibited a strong anti-plasmodial activity against the multi-drug resistant Plasmodium falciparum K1 strain (IC50 0.12 ± 0.01 μg/ml, selectivity index (SI) of 250, moderate activity against Trypanosoma brucei rhodesiense STIB 900 strain (IC50 2.50 ± 0.19 μg/ml, SI 12) and mild activity against Leishmania donovani axenic MHOM-ET-67/82 strain (IC50 9.25 ± 0.54 μg/ml, SI 3.2). Bioassay-guided chromatographic fractionation led to the isolation of four pure alkaloids, lysicamine (1), trivalvone (2), palmatine (3), jatrorrhizine (4) and two sets of mixtures of jatrorrhizine (4) with columbamine (5) and palmatine (3) with (−)-tetrahydropalmatine (6). The alkaloids showed low cytotoxicity activity (CC50 30 - >90 μg/ml), strong to moderate anti-plasmodial activity (IC50 0.08 ± 0.001 - 2.4 ± 0.642 μg/ml, SI 1.5-1,154), moderate to weak anti-trypanosomal (IC50 2.80 ± 0.001 – 14.3 ± 0.001 μg/ml, SI 2.3-28.1) and anti-leishmanial activity IC50 2.7 ± 0.001 – 20.4 ± 0.003 μg/ml, SI 1.7-15.6).ConclusionThe strong anti-plasmodial activity makes these alkaloids good lead structures for drug development programs.

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Aporphine alkaloids from Enantia chlorantha

Cited by 25 publications

References 6 publications

Antiplasmodial, anti-trypanosomal, anti-leishmanial and cytotoxicity activity of selected Tanzanian medicinal plants

Antiplasmodial, anti-trypanosomal, anti-leishmanial and cytotoxicity activity of selected Tanzanian medicinal plants

Alkaloids from Acorus gramineus rhizomes and their biological activity

Anti-protozoal activity of aporphine and protoberberine alkaloids from Annickia kummeriae (Engl. & Diels) Setten & Maas (Annonaceae)

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