Chromenes from leaves of Calea pinnatifida and evaluation of their leishmanicidal activity

Abstract

BJP 88 1-4 Revista Brasileira de Farmacognosia xxx (2015) xxx-xxx w w w . s b f g n o s i a . o r g . b r / r e v i s t a a b s t r a c t Calea pinnatifida (R. Br.) Less., Asteraceae, is popularly known as "quebra-tudo", "cipó-cruz" or "aruca". This species is used in the folk medicine for the treatment of stomach pain, giardiasis and amoebiasis. The aim of this study was to isolate and identify chromenes from leaves of C. pinnatifida and evaluate their leishmanicidal activity. A fraction from leaves of C. pinnatifida was analyzed for their chemical constituents, resulting in the isolation and characterization of four known chromenes: 6-acetyl-7-hydroxy-2,2-dimethylchromene (1), 6-acetyl-7-methoxy-2,2-dimethylchromene (2), 6-(1-hydroxyethyl)-7-methoxy-2,2-dimethylchromene (3) and 6-(1-ethoxyethyl)-7-methoxy-2,2-dimethylchromene (4). Structure identification of isolated compounds involved analysis of spectral data of 1D and 2D-NMR. The isolated compounds are here reported for the first time in C. pinnatifida, and the chromenes 1 and 3 show a moderate leishmanicidal activity.

The genus Calea L.: A review on traditional uses, phytochemistry, and biological activities

“…Baker. Eupatoriochromene (165) and methyeupatoriochromene (166) are the predominant chromenes in Calea genus (Bohlmann, Bajupi, King, & Robinson, ; Bohlmann, Fritz, et al, ; Bohlmann, Gupta, Japukovic, King, & Robinson, ; Bohlmann, Gupta, Japukovic, King, & Robinson, ; Castro et al, ; Lima et al, ; Steinbeck et al, ).…”

“…C. pinnatifida is a subshrub plant found mainly in southern and southeastern Brazil. Lima et al () investigated leishmanicidal effect of four chromenes (165–168) isolated from hexane fraction of C. pinnatifida against L. amazonensis intracellular amastigotes. Chromenes 165 and 167 demonstrated a moderate leishmanicidal activity, inhibiting parasite intracellular growth in 39.3% and 32.3%, respectively.…”

“…Many reports in the literature tender for support of the traditional uses of Calea and show that this genus contains compounds that present several biological activities, including leishmanicidal (Lima et al, ; Lima et al, ), trypanocidal (Lima et al, ; Lima et al, ), antihypertensive (Guerrero et al, ), antinociceptive, antidiarrheal (Salaga et al, ), antifungal (Flach et al, ), antiplasmodial (Kohler et al, ), acaricidal (Ribeiro, Avancini, Goncalves, Toigo, & von Poser, ), antimicrobial (Do Nascimento, Salvador, Candido, Ito, & De Oliveira, ), anti‐inflammatory (Gómez & Gil, ), antidiabetic (Roman, Alarcon‐Aguilar, Lara‐Lemus, & lores‐Saenz, ), and cytotoxic activities (Nakagawa et al, ).…”

Phytochemical investigation, antinociceptive activity and cytotoxicity of crude extracts of Calea uniflora Less.

“…C. uniflora has been little studied. Previous studies showed that this plant is rich in constituents such as lactones, sesquiterpenes, flavonoids, saponins and derivatives of p-hydroxyacetophenone (Lima et al, 2015). Other phytochemical studies by Nascimento and Oliveira (2004) showed that C. uniflora contains the compounds, glucoside-5-deoxyflavone, 3',4',7-trihydroxyflavone-7-O-β-glucopyranoside, 2',4-dihydroxy-3-methoxychalcone-40-O-β-glucopyranoside and quercetin-3-O-β-galactopyranoside.…”

“…Some species of this genus were investigated for their medicinal properties including the following: Calea pinnatifida (Lima et al, 2015) with leishmanicidal activity; Calea urticifolia (Yamada et al, 2004) used to treat oliguria and gastroenteritis; Calea zacatechichi (Leonti et al, 2003) used for dermatological/respiratory ailments and gastrointestinal purposes; Calea serrata Less. (Ribeiro et al, 2008) used to treat ulcers and liver problems and Calea glomerata (Guerrero et al, 2002) used as an antihypertensive.…”