Benzo[c]phenanthridine alkaloids from stem bark of the Forest Knobwood, Zanthoxylum davyi (Rutaceae) (original) (raw)
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Cytotoxic Benzophenanthridine and Furoquinoline Alkaloids from Zanthoxylum buesgenii (Rutaceae)
Chemistry Central Journal, 2014
Zanthoxylum buesgenii is a shrub used in Sierra Leone as remedy to cure venereal diseases, arthritis, and rheumatism whereas leaves and barks are employed to treat leprosy and to relieve pain. In South West Region of Cameroon, the plant locally called "Mbem" by Lewoh-Lebang community, is orally given to patients as aphrodisiac decoction and to increase sperm count. Previous chemical studies on Zanthoxylum species reported the identification of lignans, coumarins, diterpenes, sesquiterpenes, steroids, alkaloids and benzopropanoids. Besides, structurally diverse compounds belonging to these classes of secondary metabolites have been reported as trypanocidal, antileishmanial, antimycobacterial and cytotoxic metabolites. We therefore investigated the alkaloidal constituents of Z. buesgenii. In the course of the study, two benzophenanthridines [1-methoxy-12-methyl-12,13-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine-2,13-diol (1) and isofagaridine (2)] were identified among them one new. Alongside, three known furoquinolines [maculine (3), kokusaginine (4) and teclearverdoornine (5)] were also obtained and their structures were established on the basis of their NMR data and by comparison with those previously reported. Furthermore, the cytotoxicities of metabolites (1-4) isolated in substantial amount were evaluated against a series of multidrugs-resistant cancer cell lines. While compounds 2-4 showed selective cytotoxicities, compound 1 displayed activities against all cancer cells. The observed activities corroborate those previously reported on similar benzophenanthridine alkaloids indicating that compounds 1 and 2 can chemically be explored to develop other chemotherapeutic agents. Graphical abstractCytotoxic Benzophenanthridine and Furoquinoline Alkaloids from Zanthoxylum buesgenii (Rutaceae).
PLoS ONE, 2014
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 mg/mL using bioautography method, and from 125 to 500 mg/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 mg/mL for all bacteria tested, and between 3.12 and 6.25 mg/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.
Fitoterapia, 2016
Heitziquinone (7), a new benzophenanthridine alkaloid, together with five known compounds; isoarnottianamide (5), rhoifoline B (6), isobauerenol (8), 6-hydroxypellitorine (9) and sylvamide (10), were isolated as minor compounds from the hexane extract of stem bark from Zanthoxylum heitzii. Four previously reported compounds (1-4) were found, as well. Compounds 5 and 7 were both found to exist as 4:1 mixtures of two atropisomers. The structures were elucidated by 1D and 2D NMR spectroscopy and by mass spectrometry. Compounds 5-10 were identified for the first time in this species, and they are all rare natural compounds. Pellitorine (4), one of the main compounds from the hexane bark extract, was found to be responsible for the brine shrimp larvae toxicity (LC 50 37 µM, 8 µg/ml) of the crude extract (LC 50 24 µg/ml). Low cytotoxicity against a macrophage cell line was observed.
Quaternary Benzo[C]Phenanthridine Alkaloids — Biological Activities
NATO Science Series II: Mathematics, Physics and Chemistry, 2003
Quarternary benzo[c]phenanthridine alkaloids (QBA) are a small class of compounds commonly isolated from Caprifoliaceae, Fumariaceae, Meliacea, Papaveraceae and Rutaceae plants. QBA belong to the elicitor-inducible secondary metabolites and are considered phytoalexines because of their antifungal and nematocidal activities.
Records of Natural Products
A total of eight compounds were isolated from the petroleum ether and chloroform extracts of the root bark of Zanthoxylum rhetsa (Roxb.) (D.C). These are a coumarin xanthyletin (1), five quinolone alkaloids zanthodioline (2), arnottianamide (3), skimmianine (4), fagaridine (5), oxynitidine (7), a lignan pluviatilol (6), and a triterpene lupeol (8) were identified. Structures of the isolates were characterized by extensive 1D and 2D NMR analyses and by comparing their spectral data with the published values. The compounds, zanthodioline (2), oxynitidine (7), fagaridine (5), and pluviatilol (6) are the first record from this plant.
ChemInform, 2015
As a whole, the African continent is highly endowed with a huge floral biodiversity. Natural products which have been isolated from plants growing in this region have shown interesting chemical structures with diverse biological activities, which could serve as a starting point for drug discovery. In this study, a literature survey led to the collection of 864 secondary metabolites from 101 plant species from 57 plant families. A correlation between the known biological activities of isolated compounds and the ethnobotanical uses of the plants has been attempted. This review is a survey of the bioactivities of alkaloids and terpenoids which have been isolated from Southern African flora versus the ethnobotanical uses of the plants used in Southern African traditional medicine.
Parasite, 2007
The stem bark of Zanthoxylum rubescens (syn. Fagara rubescens) is used for treating fevers associated with malaria in the Ivory Coast. Three alkaloids: N-nornitidine, 7,9-dimethoxy-2,3methylenedioxybenzophenanthridine, and bis[6-(5,6dihydrochelerythrinyl)] ether; and two amides: zanthomamide and lemairamide, were isolated from the stem bark of this plant. These compounds were screened in vitro against the chloroquine-sensitive 3D7 strain and the chloroquine-resistant FCM29 strain of P. falciparum. N-nornitidine was found to be inactive. 7,9dimethoxy-2,3-methylenedioxybenzophenanthridine, lemairamide and zanthomamide showed weak activity with average IC 50 values ranging from 45.6 µM to 149.9 µM. Bis[6-(5,6dihydrochelerythrinyl)] ether was the most active of the tested compounds with mean IC 50s of 14.9 ± 1.4 µM in FCM29 strain and 15.3 ± 3.4 µM in 3D7 strain (~58 to ~1130 times less active than chloroquine respectively). The anti-Plasmodium activities of the tested alkaloids of Z. rubescens were low; and do not encourage the use of this plant as antimalarial. Résumé : FAIBLE ACTIVITÉ ANTIPLASMODIALE DES ALCALOÏDES ET AMIDES ISOLÉS DE L'ÉCORCE DE TIGE DE ZANTHOXYLUM RUBESCENS (RUTACEAE) Zanthoxylum rubescens (syn. Fagara rubescens) est utilisée en médecine traditionnelle pour traiter la fièvre associée au paludisme en Côte d'Ivoire. Trois alcaloïdes (N-nornitidine, 7,9-dimethoxy-2,3-methylenedioxybenzophenanthridine et bis[6-(5,6dihydrochelerythrinyl)] ether), et deux amides (zanthomamide et lemairamide) isolés de l'écore de tige de cette plante ont été testés in vitro pour évaluer leurs activités sur deux souches de Plasmodium falciparum. Les résultats obtenus ont montré que Nnornitidine est inactive et que l'activité antiplasmodiale de 7,9dimethoxy-2,3-methylenedioxybenzophenanthridine, lemairamide et zanthomamide, est faible avec des CI50 de 45,6 µM à 149,9 µM. Bis[6-(5,6-dihydrochelerythrinyl)] ether a été la plus active parmi les cinq molécules testées, cependant avec des moyennes de CI50 à 14,9 ± 1,4 µM contre la souche P. falciparum FCM29 (résistante à la chloroquine) et de 15,3 ± 3,4 µM contre la souche P. falciparum 3D7 (sensible à la chloroquine). Bis[6-(5,6-dihydrochelerythrinyl)] ether est ainsi de 58 à 1 130 fois moins actif que la chloroquine. Cette étude montre que l'activité anti-Plasmodium de ces alcaloïdes et amides de Z. rubescens ne justifie pas son utilisation de cette plante comme antipaludique.