Isolation of leishmanicidal triterpenes and lignans from the Amazonian liana Doliocarpus dentatus (dilleniaceae)

Sauvain, Michel; Kunesch, Nicole; Poisson, J; Gantier, J. C.; Gayral, Philippe; Dedet, Jean‐Pierre

doi:10.1002/(sici)1099-1573(199602)10:1<1::aid-ptr757>3.3.co;2-1

Cited by 13 publications

(15 citation statements)

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“…showed in vitro activity against Leishmania amazonensis amastigotes in infected macrophages, reducing infection by 88% at 136 mM and by 58% at 68 mM. 16 At these doses, 4 also showed some toxicity against peritoneal macrophages, with survival indices of 70 and 80%, respectively. Previously, we studied anti-leishmanial activity of heterocyclic betulin derivatives, in which the heterocycloadduct between 3,28-di-O-acetyllupa-12,18-diene and 4-methylurazine 5 was the most effective derivative with a GI 50 value of 8.9 mM against L. donovani amastigotes.…”

Section: Introductionmentioning

confidence: 99%

Anti-leishmanial activity of betulin derivatives

et al. 2010

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Leishmanicidal activity of 24 derivatives of naturally occurring and abundant triterpenes belonging to the lupane series, betulin, betulinic acid and betulonic acid, is described in this study. The easily modified positions of the lupane skeleton, the hydroxy groups of C-3 and C-28, as well as the carbon-carbon double bond C-20-C-29 were used as a starting point to prepare a library of triterpenoid derivatives for bioactivity studies. The compounds were evaluated against Leishmania donovani axenic amastigotes on a microplate assay at 50 lM. GI 50 values of the most effective compounds were evaluated, as well as their cytotoxicity on the human macrophage cell line THP-1, and anti-leishmanial activity against L. donovani-infected THP-1 macrophages was determined. Betulonic acid was the most potent derivative, yielding a GI 50 value of 14.6 lM. Promising and distinct structure-activity relationships were observed, and these compounds can be regarded as significant lead molecules for further improvement and optimization.

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Section: Introductionmentioning

confidence: 99%

Anti-leishmanial activity of betulin derivatives

et al. 2010

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“…Studies focusing on herbal remedies reported as useful for the treatment of leishmaniasis have been undertaken in French Guiana (Sauvain et al, 1993(Sauvain et al, , 1996, in Bolivia (Fournet et al, 1994), in Colombia (Weniger et al, 2001), in Brazil (Muzitano et al, 2006a,b) and in Peru (Kvist et al, 2006). Nevertheless, it is the first time that a specific ethnopharmacological study was conducted among a high Amazonian Peruvian area with strong leishmaniasis endemicity.…”

Section: Discussionmentioning

confidence: 99%

Evaluation of the leishmanicidal activity of plants used by Peruvian Chayahuita ethnic group

Estevez

Castillo

Pisango

et al. 2007

Journal of Ethnopharmacology

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“…In the subgroup of heterocyclic betulin derivatives (16)(17)(18)(19)(20), clearer structure-activity relationship trend could be observed. Compounds with sterically less bulky R3 and R4 groups showed better activity, when compared with more hindered derivatives.…”

Section: Effect Of Betulin Derivatives On Promastigote Stagementioning

confidence: 94%

“…On the other hand, 28-O-cinnamoylbetulin 2 was less active against amastigotes. From the subgroup of heterocyclic betulin derivatives (16)(17)(18)(19)(20), compounds 16, …”

Section: Effect Of Betulin Derivatives On Leishmania Amastigotes In Mmentioning

confidence: 99%

“…16,17 Some related compounds have shown antileishmanial activity against L. donovani (promastigotes and amastigotes) 18 and L. amazonensis. 19 More recently, studies have been carried out on the effect of a high number of betulinic derivatives on axenic amastigotes and amastigotes of L. donovani in the THP-1 cell line. 20 It was found that the compound with greater antileishmanial capacity (heterocycloadduct between 3.28-di-O-acetyllupa-12,18-diene and 4-methylurazine) showed a 50% growth inhibition (IC 50 ) of 8.9 mM against amastigotes, although the compound showed a 30% toxicity for the THP-1 macrophage line.…”

Section: Introductionmentioning

confidence: 99%

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Toxicity of betulin derivatives and in vitro effect on promastigotes and amastigotes of Leishmania infantum and L. donovani

et al. 2011

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The toxicity and antileishmanial activity of 20 betulin derivatives were studied. The toxicity of betulin and synthesized compounds was determined using a bacterial test (Microtox) and two mammalian cell lines (CHO-K1 and J774). The antileishmanial activity of compounds (50 lM) was examined in both the promastigote and intracellular amastigote stages of Leishmania infantum and L. donovani. No correlation was found among the toxicity tests. All the compounds showed significant antipromastigote activity. The antiproliferative capacity of derivatives was dependent on the parasite stage studied, and no substantial differences were found between Leishmania species. Betulin, 3,28-di-O-acetylbetulin and L-aspartyl amide of betulonic acid showed moderate activity against amastigotes. The highest inhibition of intracellular amastigote multiplication was achieved with a low micromolar concentration (IC 50 ca 9 lM) of heterocyclic betulin derivative 3,28-di-O-acetyllup-13(18)-ene with N-ethyltriazolo moiety 16, without significant toxicity for mammalian cells. These results point to the interest of this lead compound for further in vitro and in vivo tests.

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Isolation of leishmanicidal triterpenes and lignans from the Amazonian liana Doliocarpus dentatus (dilleniaceae)

Cited by 13 publications

References 0 publications

Anti-leishmanial activity of betulin derivatives

Anti-leishmanial activity of betulin derivatives

Evaluation of the leishmanicidal activity of plants used by Peruvian Chayahuita ethnic group

Toxicity of betulin derivatives and in vitro effect on promastigotes and amastigotes of Leishmania infantum and L. donovani

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