Antileishmanial activity of furoquinolines and coumarins from Helietta apiculata

Ferreira, Marı́a Elena; Arias, Antonieta Rojas de; Yaluff, Gloria; Bilbao, Ninfa Vera de; Nakayama, Héctor David; Torres, Susana; Schinini, Alicia; Guy, Isabelle; Heinzen, Horacio; Fournet, Alain

doi:10.1016/j.phymed.2009.09.009

Cited by 78 publications

(49 citation statements)

References 18 publications

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“…The leishmanicidal activity of several coumarins has been reported to inhibit parasite growth in vitro . Ferreira et al (2010) reported the activity against Leishmania amazonensis , Leishmania infantum and Leishmania braziliensis of nine coumarins; a second study showed a significant inhibition of L. major promatigotes in the presence of aurapten (Napolitano et al, 2004); a third study indicated significant inhibition against using coumarins such aurapten and umbelliprenin (Iranshahi et al, 2007). A lack of studies showing the antiparasitic activities of scoparone was found.…”

Section: Resultsmentioning

confidence: 99%

Different susceptibilities of Leishmania spp. promastigotes to the Annona muricata acetogenins annonacinone and corossolone, and the Platymiscium floribundum coumarin scoparone

Vila-Nova

Morais

Falcão

et al. 2013

Experimental Parasitology

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Leishmaniasis is a zoonotic disease that can manifest itself in visceral and cutaneous form. The aim of this study was to search for new leishmanicidal compounds. Preliminarily, Artemia salina assay was applied to compounds from two plants found in Northeastern Brazil, Platymiscium floribundum and Annona muricata. Then these compounds were tested against three Leishmania species (Leishmania donovani, Leishmania mexicana and Leishmania major). A screening assay using luciferase-expressing promastigote form were used to measure the viability of promastigote One coumarin, scoparone, isolated from P. floribundum and two acetogenins, annonacinone and corossolone isolated from A. muricata showed leishmanicidal activity in all species tested. Nevertheless, Leishmania species indicated different susceptibilities in relation to the tested compounds: L. mexicana was more sensitive to scoparone followed by L. major and L. donovani. The three species presented similar inhibition to corossolone and annonacinone. Acetogenin annonacinone (EC50 = 6.72 8.00 μg/mL) indicated high leishmanicidal activity; corossolone (EC50 = 16.14 18.73 μg/mL) and scoparone (EC50 = 9.11 27.51 μg/mL) moderate activity. A. saline larvae were less sensitive to the coumarin scoparone and acetogenin corossolone was the most toxic. In conclusion, the leishmanicidal activity demonstrated by the coumarin and acetogenins indicate these compounds for further studies aiming the development of new leishmanicidal agents.

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Section: Resultsmentioning

confidence: 99%

Different susceptibilities of Leishmania spp. promastigotes to the Annona muricata acetogenins annonacinone and corossolone, and the Platymiscium floribundum coumarin scoparone

Vila-Nova

Morais

Falcão

et al. 2013

Experimental Parasitology

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“…Their ability to inhibit the replication of various microorganisms, among which are Leishmania amazonensis [42], Trypanosoma cruzi [43], and Mycobacterium tuberculosis [44], and viruses, such as the human immunodeficiency virus type 1 (HIV-1) [45], and Hepatitis C [46], was also studied. In this context, our results are consistent with recent reports of the antiviral effect of certain coumarins on infection by CHIKV.…”

Section: Discussionmentioning

confidence: 99%

Antiviral effect of compounds derived from the seeds of Mammea americana and Tabernaemontana cymosa on Dengue and Chikungunya virus infections

Gómez-Calderón

Mesa-Castro

Robledo

et al. 2017

BMC Complement Altern Med

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BackgroundThe transmission of Dengue virus (DENV) and Chikungunya virus (CHIKV) has increased worldwide, due in part to the lack of a specific antiviral treatment. For this reason, the search for compounds with antiviral potential, either as licensed drugs or in natural products, is a research priority. The objective of this study was to identify some of the compounds that are present in Mammea americana (M. americana) and Tabernaemontana cymosa (T. cymosa) plants and, subsequently, to evaluate their cytotoxicity in VERO cells and their potential antiviral effects on DENV and CHIKV infections in those same cells.MethodsDry ethanolic extracts of M. americana and T. cymosa seeds were subjected to open column chromatographic fractionation, leading to the identification of four compounds: two coumarins, derived from M. americana; and lupeol acetate and voacangine derived from T. cymosa.. The cytotoxicity of each compound was subsequently assessed by the MTT method (at concentrations from 400 to 6.25 μg/mL). Pre- and post-treatment antiviral assays were performed at non-toxic concentrations; the resulting DENV inhibition was evaluated by Real-Time PCR, and the CHIKV inhibition was tested by the plating method. The results were analyzed by means of statistical analysis.ResultsThe compounds showed low toxicity at concentrations ≤ 200 μg/mL. The compounds coumarin A and coumarin B, which are derived from the M. americana plant, significantly inhibited infection with both viruses during the implementation of the two experimental strategies employed here (post-treatment with inhibition percentages greater than 50%, p < 0.01; and pre-treatment with percentages of inhibition greater than 40%, p < 0.01). However, the lupeol acetate and voacangine compounds, which were derived from the T. cymosa plant, only significantly inhibited the DENV infection during the post-treatment strategy (at inhibition percentages greater than 70%, p < 0.01).ConclusionIn vitro, the coumarins are capable of inhibiting infection by DENV and CHIKV (with inhibition percentages above 50% in different experimental strategies), which could indicate that these two compounds are potential antivirals for treating Dengue and Chikungunya fever. Additionally, lupeol acetate and voacangine efficiently inhibit infection with DENV, also turning them into promising antivirals for Dengue fever.

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“…In the AChE assay, the inhibition zone of scoparone was 0.8 cm, and was similar to the control, physostigmine (0.9cm), implying similar acetylcholinesterase inhibition characteristics. In a previous study, scoporone, was isolated from Helietta apiculata and tested against three other Leishmania promastigotes strains (L. amazonensis, L. infantum and L. braziliensis), and the results showed and EC 50 greater than 50μg/mL (Ferreira et al 2010). AChE inhibition was demonstrated for nine coumarins isolated from Ferula szowitsiana, with inhibition zones ranging from 6-8mm at a concentration of 4mg/mL (Santos et al 2008), presenting results similar to those in this study.…”

Section: Discussionmentioning

confidence: 99%

Leishmanicidal and cholinesterase inhibiting activities of phenolic compounds of Dimorphandra gardneriana and Platymiscium floribundum, native plants from Caatinga biome

Vila-Nova

Morais

Falcão³

et al. 2012

Pesq. Vet. Bras.

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In recent years, the Brazilian Health Ministry and the World Health Organization have supported research into new technologies that may contribute to the surveillance, new treatments, and control of visceral leishmaniasis within the country. In light of this, the aim of this study was to isolate compounds from plants of the Caatinga biome, and to investigate their toxicity against promastigote and amastigote forms of Leishmania infantum chagasi, the main responsible parasite for South American visceral leishmaniasis, and evaluate their ability to inhibit acetylcholinesterase enzyme (AChE). A screen assay using luciferase-expressing promastigote form and an in situ ELISA assay were used to measure the viability of promastigote and amastigote forms, respectively, after exposure to these substances. The MTT colorimetric assay was performed to determine the toxicity of these compounds in murine monocytic RAW 264.7 cell line. All compounds were tested in vitro for their anti-cholinesterase properties. A coumarin, scoparone, was isolated from Platymiscium floribundum stems, and the flavonoids rutin and quercetin were isolated from Dimorphandra gardneriana beans. These compounds were purified using silica gel column chromatography, eluted with organic solvents in mixtures of increasing polarity, and identified by spectral analysis. In the leishmanicidal assays, the compounds showed dose-dependent efficacy against the extracellular promastigote forms, with an EC50 for scoporone of 21.4µg/mL, quercetin and rutin 26 and 30.3µg/mL, respectively. The flavonoids presented comparable results to the positive control drug, amphotericin B, against the amastigote forms with EC50 for quercetin and rutin of 10.6 and 43.3µg/mL, respectively. All compounds inhibited AChE with inhibition zones varying from 0.8 to 0.6, indicating a possible mechanism of action for leishmacicidal activity.

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Antileishmanial activity of furoquinolines and coumarins from Helietta apiculata

Cited by 78 publications

References 18 publications

Different susceptibilities of Leishmania spp. promastigotes to the Annona muricata acetogenins annonacinone and corossolone, and the Platymiscium floribundum coumarin scoparone

Different susceptibilities of Leishmania spp. promastigotes to the Annona muricata acetogenins annonacinone and corossolone, and the Platymiscium floribundum coumarin scoparone

Antiviral effect of compounds derived from the seeds of Mammea americana and Tabernaemontana cymosa on Dengue and Chikungunya virus infections

Leishmanicidal and cholinesterase inhibiting activities of phenolic compounds of Dimorphandra gardneriana and Platymiscium floribundum, native plants from Caatinga biome

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