Chemical constituents from three medicinal plants: Piper renitens, Siparuna guianensis and Alternanthera brasiliana

Chemical study of three medicinal plants: from leaves of Piper renitens (Miq.) Yunck, Piperaceae, and Siparuna guianensis Aubl., Siparunaceae, and from flowers of Alternanthera brasiliana (L.) Kuntze, Amaranthaceae, resulted in isolation of nine compounds: three steroids, β-sitosterol, stigmasterol from P. renitens and sitosterol-3-O-β-D-glucopyranoside from A. brasiliana, the diterpene kaurane ent-kauran-16α,17-diol from P. renitens, two derivatives kaempferol-methylether, kumatakenine (kaempferol-3,7-dimethylether) and kaempferol-3,7,3'-trimethylether from S. guianensis and three flavones, crysoeriol (5,7,4'-trihydroxy-3'-methoxyflavone), tricin (5,7,4'-trihydroxy-3',5'-dimethoxyflavone) and 7-O-β-D-glucopyranoside-5,4'-dihydroxy-3'-methoxyflavone from A. brasiliana. Compounds structures were determinate using 1D and 2D ¹H NMR and 13C spectral data, mass and IR spectra, comparing with literature data.

Evaluation of larvicidal activity of the methanolic extracts of Piper alatabaccum branches and P. tuberculatum leaves and compounds isolated against Anopheles darlingi

Piper is a notable genus among Piperaceae due to their secondary metabolites such as lignans, amides, esters and long chain fatty acids used as anti-herbivore defenses with comparable effects of pyrethroids, that holds a promise in insect control, including malaria vectors such as Anopheles darlingi, the main vector in the North of Brazil. Methanolic extracts of Piper tuberculatum Jacq., Piperaceae, and P. alatabaccum Trel. & Yunck., Piperaceae, and some isolated compounds, i.e, 3,4,5-trimetoxy-dihydrocinamic acid, dihydropiplartine; piplartine, piplartine-dihydropiplartine and 5,5',7-trimetoxy-3',4'-metilenodioxiflavone were tested as larvicides against A. darlingi. The Lethal Concentrations (LC50 and LC90) of methanolic extracts were 194 and 333 ppm for P. tuberculatum and 235 and 401 ppm for P. alatabacum, respectively. Isolated compounds had lower LC values, e.g. the LC50 and LC90 of the piplartine-dihidropiplartine isolated from both plant species was 40 and 79 ppm, respectively.

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

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 flavones 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.

Antileishmanial activity of 3-(3,4,5-trimethoxyphenyl) propanoic acid purified from Amazonian Piper tuberculatum Jacq., Piperaceae, fruits / Atividade antileishmania do 3,4,5-trimetoxi-dihidrocinâmico purificado das frutas de Piper tuberculatum Jacq., Piperaceae, amazônica

Leishmanicidal activity of the 3-(3,4,5-trimethoxyphenyl) propanoic acid (TMPP) isolated from EtOH extracts of the Amazonian Piper turbeculatum Jacq. fruits was evaluated in vitro using Leishmania amazonensis promastigotes. The TMPP was assayed at concentrations of 1600 to 6.25 µg/mL for 24, 48, 72 and 96 h. Promastigotes viability was analyzed and the IC50 of TMPP was 145 µg/mL.

A atividade leishmanicida do ácido 3,4,5-trimetoxi-dihidrocinâmico (TMPP) isolado do extrato hidroalcoólico de frutos de Piper turbeculatum Jacq. amazônica foi testado em ensaios in vitro utilizando formas promastigotas de Leishmania amazonensis. O TMPP foi utilizado em culturas de L. amazonensis nas concentrações de 1600 a 6,25 µg/mL. A viabilidade celular das formas promastigotas foi observada em 24, 48, 72 e 96 h para cálculo da CI50. O TMPP apresentou efeito leishmanicida dose dependente para as formas promastigotas de L. amazonensis apresentando CI50 de 145 µg/mL.