Leishmanicidal and trypanocidal activity of extracts and secondary metabolites from basidiomycetes

Inchausti, Alba; Yaluff, Gloria; Árias, Antonieta Rojas de; Torres, Susana Azpiazu; Ferreira, Marı́a Elena; Nakayama, Héctor David; Schinini, Alicia; Lorenzen, K.; Anke, Timm; Fournet, Alain

doi:10.1002/(sici)1099-1573(199705)11:3<193::aid-ptr68>3.3.co;2-i

Cited by 9 publications

(10 citation statements)

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“…The final DMSO concentration did not exceed 0.5%, which has no deleterious effect on the parasites. The plate was incubated at 25 • C for 72 h, and the leishmanicidal activity was determined by direct observation through an inverted phase microscope by comparison with control cells (Muñoz et al, 1994;Inchausti et al, 1997).…”

Section: Antiprotozoal Assaymentioning

confidence: 99%

In vitro activity of Tridax procumbens against promastigotes of Leishmania mexicana

Martín-Quintal

Moo-Puc

González-Salazar

et al. 2009

Journal of Ethnopharmacology

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Section: Antiprotozoal Assaymentioning

confidence: 99%

In vitro activity of Tridax procumbens against promastigotes of Leishmania mexicana

Martín-Quintal

Moo-Puc

González-Salazar

et al. 2009

Journal of Ethnopharmacology

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“…Several sesquiterpene lactones having an a,b-unsaturated g-lactone moiety (15-deoxygoyazensolide, 15) dehydrozaluzanin C, 16) lychnopholide 17) naematolin, 18) dehydroleucodine 19) ) have been reported to show trypanocidal activity. Brengio et al reported that the effect of dehydroleucodine was irreversible, but could be blocked by simultaneous addition of a thiol compound.…”

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confidence: 93%

Trypanocidal Terpenoids from Laurus nobilis L.

et al. 2002

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Trypanosoma cruzi, a parasitic protozoan of Zoomastigophoria, is the etiologic agent of Chagas' disease which is endemic in Central and South America.1) In our screening work on medicinal plants used in Asian counties for trypanocidal activity, extracts of the dried leaves of Laurus nobilis L. (Lauraceae) showed strong trypanocidal activity against epimastigotes of T. cruzi. Leaves of L. nobilis are used as a spice known as laurel or bay leaf. They are also used as a folk medicine for rheumatism and scabies.2) Although some biological activities such as inhibition of elevation of blood ethanol level in ethanol-loaded rat, 3) inhibition of nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages, 4) induction of glutathione Stransferase activity, 5) and nematocidal activity 6) were reported for the constituents of L. nobilis, nothing has been reported on anti-protozoan constituents of this plant. Here, we report the isolation and identification of trypanocidal constituents of L. nobilis. Results and DiscussionDried leaves of Laurus nobilis were successively extracted with hexane, CHCl 3 and MeOH, and each extract was tested for anti-trypanosomal effect by the HeLa cell infection assay.7) As the CHCl 3 and MeOH extracts inhibited infection and proliferation of T. cruzi, and the MeOH extract formed the major part of the extracts, the MeOH extract was further fractionated under the guidance of in vitro trypanocidal activity against epimastigotes of T. cruzi.8) The MeOH extract was suspended in aqueous MeOH and fractionated into hexane soluble, AcOEt soluble, and water soluble fractions. Since the AcOEt soluble fraction showed the strongest activity, it was fractionated by silica gel column chromatography to give three trypanocidal compounds (1-3). These compounds were also isolated from the CHCl 3 extracts.Compounds 1 and 2 were obtained as colorless needles from hexane, mp 58-60°C, and as a colorless oil, respectively. The 1 H-and 13 C-NMR spectra indicated that both compounds were guaiane-type sesquiterpene with three exocyclic methylene moieties. Based on comparisons of the spectral data with those reported, compounds 1 and 2 were identified with dehydrocostus lactone (1) 9) and zaluzanin D (2), 10) H-detected heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond connectivity (HMBC) spectra (Fig. 1) revealed the structure to be 1-hydroperoxy-pmenthan-2-en-8-ol acetate. Treatment of 3 with PPh 3 gave an acetoxy alcohol 4, which showed oxygen-bearing carbons at d C 67.0 (C-1) and d C 84.4 (C-8). This confirmed that 3 had a hydroperoxy and an acetoxy group at positions 1 and 8, respectively. Since nuclear Overhauser effect (NOE) experiments did not provide conclusive stereochemical information, the stereochemistry of 3 was determined by chemical correlations. Photo C-NMR spectra of 7 were identical with those of the diol 8, which was derived from 3 by alkaline hydrolysis followed by reduction with PPh 3 . 12)This result established that the relative stereochemi...

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“…The growth inhibition of promastigotes was carried out following the procedure previously reported by Muñoz et al, 39 and Inchausti et al 40 Briefly, a strain of L. amazonensis (IFLA/BR/75/PH8) was grown in Schneider culture medium with 10% fetal bovine serum (FBS), penicillin (100 IU mL -1 ) and streptomycin (100 mg mL -1 ) at 25 °C; parasites in the log phase of their growth cycle were then transferred to a microplate (96 wells; 1 × 10 5 parasites/well). Stock solutions of DMSO (blank), pentamidine (positive control), crude extract, semipurified fractions and pure metabolites were diluted in Schneider medium at ≤ 100 µg mL -1 , added to the plate, and incubated for 72 h. The percentages of inhibition were obtained by directed observation of each well with an inverted phase microscope.…”

Section: Leishmanicidal Assaymentioning

confidence: 99%

Metabolites from roots of Colubrina greggii var. yucatanensis and evaluation of their antiprotozoan, cytotoxic and antiproliferative activities

Domínguez-Carmona¹,

Escalante‐Erosa²,

García‐Sosa³

et al. 2011

J. Braz. Chem. Soc.

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A purificação do extrato da raiz de Colubrina greggii var. yucatanensis levou ao isolamento e identificação do ácido 3-O-acetil ceanótico, um novo triterpeno natural, juntamente com os metabólitos já descritos: ácido ceanótico, ácido cenoténico, ácido betulínico, discarina B e crisofaneína. Os produtos naturais e os derivados semi-sintéticos éster de acetil dimetil ceanotato, dimetil ceanotato e peracetato de crisofaneína mostraram moderada a baixa atividade leishmanicida e tripanocida. Nenhum dos metabólitos mostrou ser citotóxicos ou ter atividade antiproliferativa. Os resultados também sugerem que o ácido betulínico contribui para a atividade antiplasmódica inicialmente detectada na raiz do extrato bruto de C. greggii var. yucatanensis.Purification of the root extract of Colubrina greggii var. yucatanensis resulted in the isolation and identification of 3-O-acetyl ceanothic acid as a new natural ceanothane triterpene, together with the known metabolites ceanothic acid, cenothenic acid, betulinic acid, discarine B and chrysophanein. The natural products and the semisynthetic esters acetyl dimethyl ceanothate, dimethyl ceanothate and chrysophanein peracetate showed moderate to low leishmanicidal and trypanocidal activities. None of the metabolites showed cytotoxic or antiproliferative effects. The results also suggested that betulinic acid contributes to the antiplasmodial activity originally detected in the crude root extract of C. greggii var. yucatanensis. Keywords: Colubrina greggii var. yucatanensis, Rhamnaceae, antiprotozoan, cytotoxic ceanothane IntroductionLeishmaniosis, trypanosomiosis and malaria are a group of protozoan diseases considered of significant importance due to their incidence and rate of mortality in developing countries. 1 The low effectiveness, limited availability and high toxicity of existing treatments for these illnesses emphasize the importance of continuing the search for new antiprotozoan pharmaceuticals.2 Plants are considered an important source of biologically active natural products, 3 including a number of them with antiprotozoan activity. [4][5][6] During the screening of extracts from native Yucatecan medicinal plants as potential sources of bioactive metabolites, the root extract of Colubrina greggii S. Watson var. yucatanensis M. C. Johnst., a shrub used for the treatment of liver diseases, ulcerations, abscesses, asthma and tuberculosis, 7 showedMetabolites from Roots of Colubrina greggii var. yucatanensis J. Braz. Chem. Soc. 1280 trypanocidal, antimalarial, leishmanicidal and cytostatic activity. 8,9 Previous phytochemical studies of the genus Colubrina (Rhamnaceae), which include 31 species, 10 reported the presence of a wide structural diversity of metabolites, including ansa macrolides, saponins, aporphinic alkaloids, phenolic acids, flavones and triterpenoid acids. 11-18To date, only chrysophanol, an anthraquinone with antimicrobial activity, has been reported as a metabolite from C. greggii. 19 In the present study we report the leishmanicidal, trypanocidal, a...

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Leishmanicidal and trypanocidal activity of extracts and secondary metabolites from basidiomycetes

Cited by 9 publications

References 0 publications

In vitro activity of Tridax procumbens against promastigotes of Leishmania mexicana

In vitro activity of Tridax procumbens against promastigotes of Leishmania mexicana

Trypanocidal Terpenoids from Laurus nobilis L.

Metabolites from roots of Colubrina greggii var. yucatanensis and evaluation of their antiprotozoan, cytotoxic and antiproliferative activities

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