The leishmanicidal activity of a cyclopentenedione derivative isolated from the roots of a native Amazonian pepper (Piper carniconnectivum)

Abstract

Abstract:The Piper species chemistry has been widely investigated and the phytochemical analyses have led to the isolation of a number of active compounds like alkaloids, terpenes and fl avones among others. The aim of this study was to evaluate the leishmanicidal activity of 2-[1-hydroxy-3-phenyl-(Z,2E)-2-propenylidene]-4-methyl-4-cyclopentene-1,3-dione (DCPC), a cyclopentenedione derivative isolated from the roots of Piper carniconnectivum C. DC., Piperaceae. Leishmanicidal activity against Leishmania amazonensis promastigotes was assessed, and the risk to host cell was assessed by measuring the cytotoxicity to peritoneal macrophages from BALB/c mice in vitro. L. amazonensis promastigotes and host macrophages were cultured in the presence of 100, 50, 25, 12.5 and 6 µg/mL of the cyclopentenedione derivative for up to 96 h. At the end of this period, the inhibitory concentrations (IC50) were compared with those from untreated cultures. The IC50 for promastigotes was 4.4 µg/mL after 96 h of treatment with the derivative. The 50% cytotoxic concentration (CC50) against murine peritoneal macrophages was 129 µg/mL. These results indicate that DCPC is a promising molecule for the development of leishmanicidal drugs.

The Emerging Therapeutic Potential of Nitro Fatty Acids and Other Michael Acceptor-Containing Drugs for the Treatment of Inflammation and Cancer

“…Hybrid compounds comprising an electrophilic warhead and Michael acceptor-containing structure motif (e.g., vinyl sulfone, pyrimidine nitrile group) are effective anti-malaria agents by targeting the parasitic food vacuole of P. falciparum within the low nanomolar range (Vale, 2016). Various plantderived Michael acceptors also exhibit activity against leishmaniasis, such as the cyclopentenedione derivate, DCPC, isolated from Piper carniconnectivum roots or dihydrochalcones isolated from P. elongate (Paes-Goncalves et al, 2012).…”

Antiparasitic effects of ethanolic extracts of Piper arboreum and Jatropha gossypiifolia leaves on cercariae and adult worms of Schistosoma mansoni

“…The main biological activities experimentally demonstrated for J. gossypiifolia are microbicidal (Nair et al ., 2007), larvicidal (Rahuman et al ., 2008), molluscicidal (Pereira-Filho et al ., 2014) and anti- Leishmania activities (Martins et al ., 2018). P. arboreum belongs to the Piperaceae family and is popularly known as ‘pimenta de macaco’ (Kato and Furlan, 2007; Andrade et al ., 2009; Regasini et al ., 2009; Ferreira et al ., 2010; Paes-Gonçalves et al ., 2012). Previous studies have already demonstrated some important biological activities of this plant species, such as antifungal (Silva Costa et al ., 2002), trypanosomicidal (Figueiredo et al ., 2014), leishmanicidal (Figueiredo et al ., 2014) and microbicidal activities (Regasini et al ., 2008).…”

Caracterização farmacognóstica de Piper arboreum var. arboreum e P. tuberculatum (Piperaceae)

“…arboreum e P. tuberculatum são tradicionalmente usados para fins medicinais diversos (Regasini et al 2009;Ferreira et al 2010;Paes-Gonçalves et al 2012). Investigações fitoquímicas dessas espécies identificaram compostos fixos e voláteis como alcaloides, terpenos e fenólicos (Parmar et al 1997;Facundo et al 2008;Andrade et al 2009;Regasini et al 2009).…”