5-methoxycanthin-6-one and canthin-6-one

An innovative application of the voltammetry of microparticles methodology to characterize the phytochemical composition of extracts of different parts of Zanthoxylum chiloperone var. angustifolium Engl. is described.. Characterize the phytochemical composition of extracts of different parts of plants by electrochemical methodologies.. The voltammetry of microparticles methodology was applied to alcoholic extracts from leaves, seeds, fruits, roots and stem bark of Zanthoxylum chiloperone.. In contact with aqueous phosphate buffer, characteristic cathodic signals of its main natural products (canthin-6-one, 5-methoxycanthin-6-one and trans-avicennol) were recorded. The study of the voltammograns allows the estimation of the relative amounts of canthin-6-one, 5-methoxycanthin-6-one and trans-avicennol from the different parts of Zanthoxylum chiloperone.. The voltammetric responses of alcoholic extracts from different parts of Zanthoxylum chiloperone var. angustifolium allows their phytochemical characterization without need of sample pretreatment thus illustrating the capabilities of the voltammetry of microparticles methodology to increase the tools applied to phytochemical analysis. Copyright © 2016 John Wiley & Sons, Ltd.

Topics: Carbolines; Coumarins; Electrochemical Techniques; Indole Alkaloids; Phytochemicals; Plant Extracts; Pyrones; Zanthoxylum

Zanthoxylum chiloperone var. angustifolium was investigated. Alkaloids 1-3 from the canthin-6-one series were characterized. Derivatives 7-28 were prepared by hemisynthesis or total synthesis. All compounds were tested for in vitro antifungal activities against five pathogenic fungal strains. Analogues of canthin-6-one did not show better antifungal activities.

Topics: Alkaloids; Antifungal Agents; Aspergillus fumigatus; Candida albicans; Carbolines; Cryptococcus neoformans; Drug Evaluation, Preclinical; Indole Alkaloids; Indoles; Microbial Sensitivity Tests; Molecular Structure; Naphthyridines; Plants, Medicinal; Saccharomyces cerevisiae; Structure-Activity Relationship; Trichophyton; Zanthoxylum

An alkaloidal extract of the stem barks of Zanthoxylum chiloperone var. angustifolium exhibited antifungal activity against Candida albicans, Aspergillus fumigatus and Trichophyton mentagrophytes var. interdigitale using a TLC bioautographic method. Bioassay-guided fractionation of this extract resulted in the isolation of two active compounds identi fi ed as canthin-6-one and 5-methoxycanthin-6-one. Canthin-6-one exhibited a broad spectrum of activities against Aspergillus fumigatus, A. niger, A. terreus, Candida albicans, C. tropicalis, C. glabrata, Cryptococcus neoformans, Geotrichum candidum, Saccharomyces cerevisiae, Trichosporon beigelii, Trichosporon cutaneum and Trichophyton mentagrophytes var. interdigitale with MICs values between 5.3 and 46 micro mol/L. 5-methoxy-canthin-6-one was active against only Trichophyton mentagrophytes var. interdigitale with a MIC value of 12.3 micro mol/L.

Topics: Antifungal Agents; Aspergillus fumigatus; Candida albicans; Carbolines; Humans; Indole Alkaloids; Indoles; Ketoconazole; Microbial Sensitivity Tests; Mitosporic Fungi; Naphthyridines; Phytotherapy; Plant Extracts; Trichophyton; Zanthoxylum

The crude alkaloidal extract of Zanthoxylum chiloperone stem bark exhibited in vitro activity against various strains of Leishmania ssp. at 100 microg/ml. Two active major constituents were isolated and identified as canthin-6-one and 5-methoxycanthin-6-one. The effect of these compounds was also tested in an in vivo assay using BALB/c mice infected with Leishmania amazonensis. The mice were treated for 5 weeks postinfection with these alkaloids by oral (14 days) or intralesional route (4 days) at 10 mg/kg daily. The reference drug, N-methylglucamine antimonate was administered by subcutaneous injections at 100 mg/kg for 10 days. Intralesional administration of canthin-6-one reduced the parasite burden but not significantly when it was compared with the untreated group, while the reference drug reduced by 91% the parasite loads in the lesion.

Topics: Alkaloids; Animals; Carbolines; Female; Indole Alkaloids; Indoles; Leishmania; Leishmaniasis; Male; Mice; Mice, Inbred BALB C; Naphthyridines; Phytotherapy; Plant Preparations; Trypanocidal Agents; Zanthoxylum