Chemical Constituents of the Bark of Zanthoxylum gilletii (Rutaceae) and Their In Vitro Antiplasmodial and Molecular Docking Studies (original) (raw)
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Alkaloids and Their Pharmacology Effects from Zanthoxylum Genus
Alkaloids [Working Title]
Zanthoxylum genus (Rutaceae) comprises about 212 species distributed in warm temperature and subtropical areas in the worldwide. Zanthoxylum species have been used in traditional for the treatment of tooth decay, snakebites, blood circulation problems, stomach problems, inflammation, rheumatic, and parasitic diseases. The chemical investigations of Zanthoxylum have been studied by many scientists over the world. Several classes of compounds have been isolated from this genus such as alkaloids, coumarins, and monoterpenes. Of these, alkaloids are the main components and play an important role in Zanthoxylum species. Alkaloids have been shown the potential promise about biological activities: cytotoxic, antimalarial, leishmanicidal, anti-inflammatory, analgesic, antiviral, and antibacterial activities. This chapter will focus on the structure elucidation and pharmacological activities of alkaloids from Zanthoxylum species. In addition, the absolute configuration of some alkaloids from Zanthoxylum genus will be also discussed.
Bioscience Journal
The Brazilian flora is known for its vast biodiversity; however, many species have been still little studied regarding to their chemical composition and biological potential. Thus, this study aimed to determine the antimicrobial, antioxidant and acaricidal activity of the extracts of leaves of Zanthoxylum caribaeum L. In addition, phytochemical screening of these extracts was carried out to determine the main classes of secondary metabolites present in Z. caribaeum. Using the Z. caribaeum leaves, the aqueous extract and extracts were obtained in organic solvents (ethanol, methanol, hexane, acetone, dichloromethane and ethyl acetate). The antimicrobial activity of extracts was determined by broth microdilution method, and to detect antioxidant activity the method of capturing the free radical 2,2-diphenyl-1-picryl hydrazyl (DPPH) was used. The acaricidal activity of the extracts was tested on Dermanyssus gallinae (De Geer) (Acari: Dermanissidae). Ethanolic and methanolic extracts pr...
Helvetica Chimica Acta, 2012
A new cyclopeptide, cyclozanthoxylane A (1), the lignans cis-and trans-methylpluviatolide, the flavonoid isoquercitrin, along with a mixture of benzoic and cinnamic acid derivatives, were isolated from the MeOH extract of the leaves of Zanthoxylum rigidum (Rutaceae). The structures of the compounds were determined on the basis of 1D-and 2D-NMR, and MS analysis. It is the first time that a natural cyclic peptide has been isolated from the genus Zanthoxylum.
Pharmacognosy Communications, 2017
Introduction: Multidrug resistance remains a major obstacle hindering successful antimalarial chemotherapy. In the current study, 50% methanol in dichloromethane extract and six compounds from the stem bark of Zanthoxylum gilletii were explored for their antiplasmodial potential against three strains of Plasmodium falciparum. Materials and Methods: The extract was obtained by cold percolation using 50 % MeOH in CH 2 Cl 2 and the antiplasmodial activities were assayed using a non-radioactive Malaria SYBR Green I assay to determine a concentration that inhibits growth of 50% of parasites in culture (IC 50). Results and Discussion: Chromatographic separation of the crude extract yielded six known compounds including: one lignan, sesamin (1), an alkamide, fagaramide (2), three benzo [c] phenanthridine alkaloids, 8-acetonyldihydrochelerythrine (3), dihydrochelerythine (4), norchelerythrine (5) and one pentacyclic triterpenoid, lupeol (6). The extract and sesamin (1) showed promising antiplasmodial activities against the chloroquine resistant (W2), chloroquine sensitive (D6) and 3D7 strains of P. falciparum, with IC 50 values of 2.52, 1.48 and 1.43 µg/mL and 5.4, 9.1 and 8.3 µM, respectively. To the best of our knowledge, this is the first report on antiplasmodial activities of the stem bark extract (50% MeOH in CH 2 Cl 2) and compound 1-3 and 6. Furthermore, three of the isolated compounds; 1, 3, 6 are reported from this species for the first time. Conclusion: The good antiplasmodial activities exhibited by the stem bark of Z. gilletii against three different strains of P. falciparum may be attributed to the presence of 1-3 exhibiting good activities against all strains of P. falciparum.
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.
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.
Phytochemistry and Pharmacology of Zanthoxylum gilletii: A Review
Archives of Current Research International
Aim: Zanthoxylum gilletii is used in traditional medicine against several pains, namely urinary tract infections, malaria, lombargy, high blood pressure etc. Thus, the aim of this study was to review the literature on the traditionnal use, the phytochemical composition and the biological activities of the above-mentioned plant. Methodology: A literature review was conducted based on the scientific results sourced from Science Direct, PubMed, Google Scholar, SciLEO and PubMed Central. The plant scientific name was used as a search keyword together with the following words phytochemistry, pharmacology, bioactivity and pharmacognosia. Results: Z. gilletii extracts have shown antimicrobial, antifungal, antiparasitic and anticancer activities. Several compounds have been reported from different parts of the plant including alkaloids, amides, coumarins and essential oils and have shown interesting biological properties such as the antioxidant and antimicrobial activities. However, ther...
A New Cycloheptapeptide from Zanthoxylum mezoneurispinosum Aké Assi (Rutaceae)
Mediterranean Journal of Chemistry, 2014
A new cycloheptapeptide named akeassimezorine 1 and twelve known compounds: methoxy-chelerythrine 2, chelerythrine 3, nitidine 4, methoxyfagaridine 5, jatrorrhizine 6, tembetarine 7, N-methylatanine 8, magnoflorine 9, skimmianine 10, sesamine 11, hesperidine 12, and lupeol 13 were isolated from the roots of Zanthoxylum mezoneurispinosum Aké Assi (Rutaceae). The structures of those compounds were elucidated on the basis of one- and two-dimensional NMR and HR-ESI-MS analyses. Antibacterial activity of compound 1 was evaluated against pathogenic agents. This study constituted the first phytochemical investigation of the roots of Zanthoxylum mezoneurispinosum.