Antiplasmodial activities of furoquinoline alkaloids from <i>Teclea afzelii</i>

Wansi, Jean Duplex; Hussain, Hidayat; Tcho, Alain Tadjong; Kouam, Siméon F.; Specht, Sabine; Sarite, Salem Ramadan; Hoerauf, Achim; Krohn, Karsten

doi:10.1002/ptr.2894

Cited by 28 publications

(23 citation statements)

References 13 publications

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“…Furoquinoline alkaloids ( 181-184 ) have been obtained from Teclea afzelii (Rutaceae). When evaluated against P. falciparum (NF54) in vitro, 3 µM of compounds 181-184 showed a partial suppression of parasitic growth [ 70 ]. The azafluorenone 5-hydroxy-6-methoxyonychine ( 185 ) obtained from Mitrephora diversifolia (Annonaceae) was shown to be active against P. falciparum strains 3D7 and Dd2, with IC 50 values of 9.9 and 11.4 μM, respectively [ 71 ].…”

Section: Alkaloidsmentioning

confidence: 99%

Antiplasmodial Natural Products

2011

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Malaria is a human infectious disease that is caused by four species of Plasmodium. It is responsible for more than 1 million deaths per year. Natural products contain a great variety of chemical structures and have been screened for antiplasmodial activity as potential sources of new antimalarial drugs. This review highlights studies on natural products with antimalarial and antiplasmodial activity reported in the literature from January 2009 to November 2010. A total of 360 antiplasmodial natural products comprised of terpenes, including iridoids, sesquiterpenes, diterpenes, terpenoid benzoquinones, steroids, quassinoids, limonoids, curcubitacins, and lanostanes; flavonoids; alkaloids; peptides; phenylalkanoids; xanthones; naphthopyrones; polyketides, including halenaquinones, peroxides, polyacetylenes, and resorcylic acids; depsidones; benzophenones; macrolides; and miscellaneous compounds, including halogenated compounds and chromenes are listed in this review.

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Section: Alkaloidsmentioning

confidence: 99%

Antiplasmodial Natural Products

2011

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“…These plants are known to be a rich source of natural products, mainly alkaloids and lignans. Some of these alkaloids, including the benzophenanthridines and furoquinolines, display a variety of biological activities, such as antitumor [6]–[11], antimicrobial [12], anti-inflammatory [13]–[15] and antiplasmodial [16]–[18] activity.…”

Section: Introductionmentioning

confidence: 99%

Structure-Activity Relationship of Benzophenanthridine Alkaloids from Zanthoxylum rhoifolium Having Antimicrobial Activity

et al. 2014

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Zanthoxylum rhoifolium (Rutaceae) is a plant alkaloid that grows in South America and has been used in Brazilian traditional medicine for the treatment of different health problems. The present study was designed to evaluate the antimicrobial activity of the steam bark crude methanol extract, fractions, and pure alkaloids of Z. rhoifolium. Its stem bark extracts exhibited a broad spectrum of antimicrobial activity, ranging from 12.5 to 100 µg/mL using bioautography method, and from 125 to 500 µg/mL in the microdilution bioassay. From the dichloromethane basic fraction, three furoquinoline alkaloids (1–3), and nine benzophenanthridine alkaloids (4–12) were isolated and the antimicrobial activity of the benzophenanthridine alkaloids is discussed in terms of structure-activity relationships. The alkaloid with the widest spectrum of activity was chelerythrine (10), followed by avicine (12) and dihydrochelerythrine (4). The minimal inhibitory concentrations of chelerythrine, of 1.50 µg/mL for all bacteria tested, and between 3.12 and 6.25 µg/mL for the yeast tested, show this compound to be a more powerful antimicrobial agent when compared with the other active alkaloids isolated from Z. rhoifolium. To verify the potential importance of the methylenedioxy group (ring A) of these alkaloids, chelerythrine was selected to represent the remainder of the benzophenanthridine alkaloids isolated in this work and was subjected to a demethylation reaction giving derivative 14. Compared to chelerythrine, the derivative (14) was less active against the tested bacteria and fungi. Kinetic measurements of the bacteriolytic activities of chelerythrine against the bacteria Bacillus subtilis (Gram-positive) and Escherichia coli (Gram-negative) were determined by optical density based on real time assay, suggesting that its mechanism of action is not bacteriolytic. The present study did not detect hemolytic effects of chelerythrine on erythrocytes and found a protective effect considering the decrease in TBARS and AOPP (advanced oxidized protein products) levels when compared to the control group.

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“…Wansi et al (2010) have reported that the compound kokusaginine (1) (furoquinoline alkaloid) was isolated from the MeOH extract of the stem of Teclea afzelii showed partial inhibitory effect at 4 μM and an even stronger effect at 8 μM compared with CQ against the in vitro treatment of the CQ-sensitive strain of P. falciparum (NF54).The compound fagaronine, a derivative of the root extract of Fagara zanthoxyloides, inhibited the growth of P. falciparum and showed a significantly low IC 50 of 0.018 μg/mL (Kassim et al 2005). The activity of the aqueous, chloroform, and methanol extracts from Zanthoxylum usambarense on Plasmodium knowlesi showed the IC 50 values were 6.04, 3.14, and 6.12 μg/mL, respectively (Were et al 2010), and the IC 50 value for the aqueous extract from the same plant fell between 6 and 15 μg/mL against both CQ-sensitive and resistant P. falciparum strains, while that of methanolic extract was found to be lower than 6 μg/mL (Kirira et al 2006).…”

Section: Resultsmentioning

confidence: 97%

Antiplasmodial activity of botanical extracts against Plasmodium falciparum

Bagavan¹,

Rahuman²,

Kamaraj³

et al. 2010

Parasitol Res

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The absence of a vaccine and the rampant resistance to almost all antimalarial drugs have accentuated the urgent need for new antimalarial drugs and drug targets for both prophylaxis and chemotherapy. The aim of the study was to discover effective plant extracts against Plasmodium falciparum. In the present study, the hexane, chloroform, ethyl acetate, acetone, and methanol extracts of Citrus sinensis (peel), Leucas aspera, Ocimum sanctum, Phyllanthus acidus (leaf), Terminalia chebula (seed) were tested for their antimalarial activity against chloroquine (CQ)-sensitive (3D7) strain of P. falciparum which was cultured following the candle-jar method. Antimalarial evaluations of daily replacement of culture medium containing CQ and different plant crude extracts were performed on 96-well plates at 37°C for 24 and 48 h. Parasitemia was determined microscopically on thin-film Giemsa-stained preparations. Plant extracts were tested for their cytotoxicity using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay on human laryngeal cancer cell line (HEp-2) and normal cell line (Vero). Out of the 25 extracts tested, six showed good (IC(50) 4.76-22.76 μg/mL), 15 exhibited moderate (IC(50) 31.42-88.03 μg/mL), while four displayed mild (IC(50) > 100 μg/mL) antiplasmodial activity. The leaf ethyl acetate and methanol extracts of L. aspera; ethyl acetate, acetone, and methanol extracts of P. acidus; and seed acetone extract of T. chebula had good antiplasmodial activity (IC(50) = 7.81, 22.76, 9.37, 14.65, 12.68, and 4.76 μg/mL) with selectivity indices 5.43, 2.04, 4.88, 3.35, 3.42, and 9.97 for HEp-2 and >5.79, >2.20, >11.75, >3.41, >3.94, and >7.38 for Vero cells, respectively. These analyses have revealed for the first time that the components present in the solvent extracts of L. aspera, P. acidus, and T. chebula have antiplasmodial activity. The high antiplasmodial activity observed make these plants good candidates for isolation of anti-protozoal compounds which could serve as new lead structures for drug development.

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Antiplasmodial activities of furoquinoline alkaloids from Teclea afzelii

Cited by 28 publications

References 13 publications

Antiplasmodial Natural Products

Antiplasmodial Natural Products

Structure-Activity Relationship of Benzophenanthridine Alkaloids from Zanthoxylum rhoifolium Having Antimicrobial Activity

Antiplasmodial activity of botanical extracts against Plasmodium falciparum

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