Antifungal compounds from Zanthoxylum chiloperone var. angustifolium

Abstract

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.

The antiplasmodium effects of a traditional South American remedy: Zanthoxylum chiloperone var. angustifolium against chloroquine resistant and chloroquine sensitive strains of Plasmodium falciparum

“…A decoction of Z. chiloperone root and stem bark has been used in traditional medicine to treat malaria and for its emmenagogue and antirheumatic properties (Ferreira et al, 2007;Milliken, 1997). Recent studies have shown that the crude extract of the stem bark and leaves have activity against Trypanosoma cruzi (Ferreira et al, 2011;Ferreira et al, 2002) and antifungal activity in vitro (Thouvenel et al, 2003). Further investigations demonstrate that canthinone type alkaloids, canthin-6-one and 5-methoxycanthin-6-one, are antifungal (Soriano-Agatόn et al, 2005;Thouvenel et al, 2003) and effective in vivo against Leishmania amazonensis and Trypanosoma cruzi (Ferreira et al, 2011;Ferreira et al, 2007;Ferreira et al, 2002).…”

“…Recent studies have shown that the crude extract of the stem bark and leaves have activity against Trypanosoma cruzi (Ferreira et al, 2011;Ferreira et al, 2002) and antifungal activity in vitro (Thouvenel et al, 2003). Further investigations demonstrate that canthinone type alkaloids, canthin-6-one and 5-methoxycanthin-6-one, are antifungal (Soriano-Agatόn et al, 2005;Thouvenel et al, 2003) and effective in vivo against Leishmania amazonensis and Trypanosoma cruzi (Ferreira et al, 2011;Ferreira et al, 2007;Ferreira et al, 2002). Canthin-6-one has been suggested to be an inexpensive and safe treatment for use in long-term oral treatment as well as a good candidate against drug resistant strains of T. cruzi.…”

An Unusual Series of Thiomethylated Canthin‐6‐ones from the North American Mushroom Boletus curtisii

“…One of the colorless compounds, C 14 H 8 N 2 O, was identified by its spectroscopic data, including the 1 H-coupled 13 C NMR spectrum, [1] as canthin-6-one (1), [2] an alkaloid known from several plants of the Rutaceae, Simaroubaceae, and Amaranthaceae families. [3] Canthin-6-one exhibits antifungal [4] and cytotoxic [5] properties. A second colorless compound 2, C 15 H 10 N 2 OS, is a methylthio derivative of canthin-6-one.…”

Atividades farmacológicas dos extratos de Zanthoxylum chiloperone (Rutaceae)

“…Tribos indígenas do Paraguai usa a espécie como antimalárico, enemagogo, anti-reumático, antimicrobiano e para dor de cabeça (Milliken 1997;Guy et al, 2001). Estudos fi toquímicos de Z. chiloperone identifi caram alcalóides e óleos essenciais (SorianoAgatón et al, 2005;Thouvenel et al, 2003;Ferreira et al, 2002). Atividades leishmanicida e antifúngica (Thouvel et al, 2003;Ferreira et al, 2002), assim como tripanomicida (Ferreira et al, 2007), foram atribuídas a substâncias isoladas desta espécie.…”