Trypanocidal and Antileishmanial Dihydrochelerythrine Derivatives from <i>Garcinia lucida</i>

Fotie, Jean; Bohle, D. Scott; Olivier, Martin; Gómez, María Adelaida; Nzimiro, Sandra

doi:10.1021/np0702281

Cited by 69 publications

(36 citation statements)

References 16 publications

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“…18 Previous publications, 17,18 however, reported the isolation of the unstable parent alkaloids avicine and nitidine. Although acetone derivatives of avicine and nitidine have been reported in the literature, [19][20][21] as well as acetone aducts of two other benzophenantridine alkaloids, 22,23 it is controversial, however, whether those acetone derivatives are really present on the plant extract or were isolated as artifacts, due to the greater stability of the acetone aducts as compared to the parent alkaloids avicine and nitidine. …”

Section: Resultsmentioning

confidence: 99%

6-acetonyl-N-methyl-dihydrodecarine, a new alkaloid from Zanthoxylum riedelianum

Fernandes¹,

Vieira²,

Silva³

et al. 2009

J. Braz. Chem. Soc.

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Um novo alcalóide benzofenantridínico, 6-acetonil-N-metil-diidrodecarina foi isolado das raízes de Zanthoxylum riedelianum juntamente com lupeol, 6-acetonildiidroqueleritrina e 6-acetonildiidroavicina. As estruturas dessas substâncias foram estabelecidas com base na análise dos dados espectrométricos de IV, EM e RMN incluindo experimentos 2D.A new benzophenanthridine alkaloid, 6-acetonyl-N-methyl-dihydrodecarine was isolated from Zanthoxylum riedelianum roots together with lupeol, 6-acetonyldihydrochelerythrine and 6-acetonyldihydroavicine. The structures were established from the IR, MS and NMR spectral data, including 2D-NMR experiments. Keywords: Zanthoxylum riedelianum, Rutaceae, benzophenanthridine alkaloids IntroductionThe Zanthoxylum genus (Rutaceae) is composed by more than 200 species and largely distributed around the world. 1 Chemically, this genus is characterized by alkaloids, 2-7 cumarins, 5,6,8 lignans, 4,9,10 amides 11,12 and terpenes. 5,6,13,14 Ongoing studies have shown that Zanthoxylum exhibit a range of biological activities such as antichagas, 2 tripanocidal, 9 antiplasmodial, 7 anti-HIV 13 and antiinflammatory, 8,10 as well as antihelmintic. 12 Z. riedelianum is used in folk medicine as a decoction against different types of inflammations, rheumatism and skin stains. 15 Previous works reported the identification of terpenes from the essential oil 14 and lignans from the leaves and the stem bark. 10 In this work we report the isolation and structural elucidation of a novel benzophenanthridine alkaloid, namely, 6-acetonyl-N-methyl-dihydrodecarine (1), together with two known alkaloids 6-acetonyldihydrochelerythrine (2) and 6-acetonyldihydroavicine (3) from the roots of Z. riedelianum. Experimental General proceduresMelting points were uncorrected. IR spectra were recorded on FTIR-Bomem-MB/100 model spectrophotometer using NaCl film. NMR spectra in CDCl 3 , were recorded on Bruker ARX-400 (400 MHz for 1 H and 100 MHz for 13 C); Bruker AC-200 (200 MHz for 1 H and 50 MHZ for 13 C) and Varian-Mercury 300 (300 MHz for 1 H and 75 MHz for 13 C) spectrometers, using tetramethylsilane (TMS) as internal standard. Electron Ionization Mass Spectra (ESI-MS) was undertaken employing a Quatro LC-Micromass UK model spectrometer. Optical rotations were determined on a Perkin-Elmer 341 polarimeter. CC: silica gel (Merck 70-230 mesh ASTM); TLC: silica gel G 60 and silica gel 60 PF 254 (Merck) were used to analyze the fractions collected from column chromatography (CC) with visualization by UV (254 and 366 nm), Dragendorff´s reagent and exposure to iodine vapor. Plant materialZanthoxylum riedelianum (Engl.) was collected in Rio Manso Highway, km 22, Chapada dos Guimarães, Mato 6-Acetonyl-N-methyl-dihydrodecarine, a New Alkaloid from Zanthoxylum riedelianum J. Braz. Chem. Soc. 380 Grosso State, Brazil. A voucher specimen (No. 24.080) was deposited at Universidade Federal de Mato Grosso Central Herbarium. Extraction and isolationDried roots (3.0 kg) were powdered and extracted with hexane and methanol by mac...

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Section: Resultsmentioning

confidence: 99%

6-acetonyl-N-methyl-dihydrodecarine, a new alkaloid from Zanthoxylum riedelianum

Fernandes¹,

Vieira²,

Silva³

et al. 2009

J. Braz. Chem. Soc.

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“…To our knowledge, there was no previous report on the antimicrobial activities on beta-lactamresistant bacteria or the chemical natures of the potentially antimicrobial compounds of the 12 plant species investigated in the present study. However, some studies revealed the presence of bergapten, coumarin, beta-sitosterol, beta-sitosterol glucopyranoside, oleanolic, naringenic acid, and prorepensin in D. picta [22]; flavonoids and xanthones in G. kola [23,24], cycloartane derivatives, anthocyane, flavonoids, saponins triterpenes and alkaloids in G. lucida [25][26][27], friedelin, taraxerone, epifriedelinol, taraxerol in B. micrantha [28,29], sterols in P. africanus [30]. It is probable that some of these compounds, alone or in combination, are responsible for the observed antimicrobial properties as previously shown.…”

Section: Discussionmentioning

confidence: 99%

“…Concerning the safety of the plants studied, G. lucida has little toxicity to Vero cells and the host cells [25], whereas the extract of B. micrantha is cytotoxic and possess acute systemic toxicity [34].…”

Section: Zenkerimentioning

confidence: 99%

The in-vitro antimicrobial activity of some medicinal plants against β-lactam-resistant bacteria

Gangoué-Piéboji

Eze

Djintchui

et al. 2009

J Infect Dev Ctries

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Background: In effort to identify novel bacterial agents, this study was initiated to evaluate the antimicrobial properties of 17 crude extracts from 12 medicinal plants against beta-lactam-resistant bacteria. Methodology: The antimicrobial activities of plant extracts were evaluated against clinically proved beta-lactam-resistant bacteria (Klebsiella pneumoniae, Klebsiella oxytoca, Enterobacter cloacae, Serratia marcescens, Acinetobacter baumannii, Staphylococcus aureus and Enterococcus sp.) and reference strains of bacteria (Escherichia coli ATCC 35218, Enterobacter aerogenes ATCC 29751, E. aerogenes ATCC 13048, Pseudomonas aeruginosa ATCC 27853 and Enterococcus hirae ATCC 9790) by using disc-diffusion and agar-dilution assays. Results: The crude plant extracts demonstrated broad spectrum activity against all bacteria tested with inhibition zones in the range of 8-30 mm. The minimal inhibitory concentration (MIC) values of different plant extracts against the tested bacteria were found to range from ≤ 0.3 to ≥ 10 mg ml -1 . The most active plant extracts were from Dortenia picta and Bridelia micrantha (MIC: 1.25-10 mg ml -1 ) on beta-lactamresistant Gram-negative bacilli and the extracts from B. micrantha, Mallotus oppositifolius, Garcinia lucida, Garcinia. kola, Campylospermum densiflorum (leaves) and C. zenkeri (root) on beta-lactam-resistant Gram-positive cocci (MIC: ≤ 0.3-5 mg ml -1 ). Conclusion: Of the 17 plant extracts studied, seven showed good antimicrobial activity against the tested bacteria. The stem bark of B. micrantha and the leaves of D. picta were most active towards beta-lactamase producing Gram-negative bacilli. This study shows that medicinal plants could be sources of compounds which can be used to fight against beta-lactam resistant bacteria.

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“…Antiplasmodial (IC 50 , µg/ml) and cytotoxic (CC 50 , µg/ml) activities, and selective index of samples from B. sumatrana leaves against chloroquine-sensitive NF54 and chloroquine-resistant K1 strains of P. falciparum (IC 50 , µg/ml). complex composition, purification might lead to the isolation pure compounds with highly increased activity.…”

Section: Antiprotozoal and Cytotoxic Effectsmentioning

confidence: 99%

“…In the cytotoxic studies, it was observed that except ME-1.3 and ME-1.4 samples devoid with cytotoxic effect against MRC-5 cell line (CC 50 > 64 and 34.24 µg/ml respectively) since their CC 50 are greater than 32 µg/ml, the remaining samples were cytotoxic with CC 50 values ranged from <0.25 to 24.05 µg/ml since their respective CC 50 were weaker than 32 µg/ml [17].…”

Section: Cytotoxic and Selective Effects Of Samples Of B Sumatrana Lmentioning

confidence: 99%

Study of Antiparasitic and Cytotoxicity of the Aqueous, the 80% Methanol Extract and Its Fractions, and the Acute Toxicity of the Aqueous Extract of <i>Brucea sumatrana</i> (Simaroubaceae) Leaves Collected in Mai-Ndombe, Democratic Republic of Congo

Ehata¹,

Lumpu²,

Munduku³

et al. 2016

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Results from the in vitro evaluation of the antiparasitaire activity of the aqueous extract, the 80% methanol extract and its fractions from the leaves of Brucea sumatrana against Trypanosoma brucei brucei, T. cruzi, Leishmania infantum, the multidrugresistant K1 and chloroquine-sensitive NF54 strains of Plasmodium falciparum indicated that all samples from the leaves extract presented interesting antiparasitaire activity at different extents. The 80% methanol extract, its chloroform acid, petroleum ether and 80% methanol soluble fractions and the aqueous extract exhibited strong activity against Trypanosoma b. brucei, T. cruzi, L. infantum and the multidrug-resistant K1 strain of P. falciparum with IC 50 values from <0.25 to 4.35 µg/ml as well as against chloroquine-sensitive NF54 strain of P. falciparum with IC 50 values ranging from <0.02 to 2.0.4 µg/ml. Most samples were cytotoxic against MRC-5 cell lines (0.2 < cytotoxic concentration 50(CC 50 ) < 34.24 µg/ml) and showed good selective effect against all tested parasites. In acute toxicity, the aqueous extract was found to be non-toxic and its LD 50 was estimated to be greater than 5 g/kg. In addition, it did not significantly modify the concentration levels of some evaluated biochemical How to cite this paper: Ehata, M.T., Lumpu, S.N., Munduku, C.K., Kabangu, O.K., Cos, P., Maes, L., Apers, S., Vlietinck, A.J., Pieters, L. and Kanyanga, R.C. (2016) 94and hematological parameters in treated rats. These results constitute a scientific validation supporting and justifying the traditional use of the leaves of B. sumatrana for the treatment of malaria, sleeping sickness and at some extent Chagas disease.

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Trypanocidal and Antileishmanial Dihydrochelerythrine Derivatives from Garcinia lucida

Cited by 69 publications

References 16 publications

6-acetonyl-N-methyl-dihydrodecarine, a new alkaloid from Zanthoxylum riedelianum

6-acetonyl-N-methyl-dihydrodecarine, a new alkaloid from Zanthoxylum riedelianum

The in-vitro antimicrobial activity of some medicinal plants against β-lactam-resistant bacteria

Study of Antiparasitic and Cytotoxicity of the Aqueous, the 80% Methanol Extract and Its Fractions, and the Acute Toxicity of the Aqueous Extract of <i>Brucea sumatrana</i> (Simaroubaceae) Leaves Collected in Mai-Ndombe, Democratic Republic of Congo

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Trypanocidal and Antileishmanial Dihydrochelerythrine Derivatives from Garcinia lucida

Cited by 69 publications

References 16 publications

6-acetonyl-N-methyl-dihydrodecarine, a new alkaloid from Zanthoxylum riedelianum

6-acetonyl-N-methyl-dihydrodecarine, a new alkaloid from Zanthoxylum riedelianum

The in-vitro antimicrobial activity of some medicinal plants against β-lactam-resistant bacteria

Study of Antiparasitic and Cytotoxicity of the Aqueous, the 80% Methanol Extract and Its Fractions, and the Acute Toxicity of the Aqueous Extract of &lt;i&gt;Brucea sumatrana&lt;/i&gt; (Simaroubaceae) Leaves Collected in Mai-Ndombe, Democratic Republic of Congo

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Study of Antiparasitic and Cytotoxicity of the Aqueous, the 80% Methanol Extract and Its Fractions, and the Acute Toxicity of the Aqueous Extract of <i>Brucea sumatrana</i> (Simaroubaceae) Leaves Collected in Mai-Ndombe, Democratic Republic of Congo