Toxic Effects of Natural Piperine and Its Derivatives on Epimastigotes and Amastigotes of Trypanosoma cruzi.

Ribeiro, Tatiana S.; Freire-de-Lima, Leonardo; Previato, José O.; Mendonça-Previato, Lúcia; Heise, Norton; Lima, Maro Edilson Freire de

doi:10.1002/chin.200443205

Cited by 13 publications

(21 citation statements)

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“…Kapil (1993) reported an investigation of piperine (amide 6) activity against promastigote forms of Leishmania donovani. More recently, Ribeiro et al (2004) reported the highly significant trypanocidal activity of piperine and its synthetic derivatives on epimastigotes and amastigotes of T. cruzi.…”

Section: Resultsmentioning

confidence: 99%

Trypanocidal activity of Piper arboreum and Piper tuberculatum (Piperaceae)

Regasini¹,

Cotinguiba²,

Passerini³

et al. 2009

Rev. bras. farmacogn.

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RESUMO: "Atividade tripanocida dePiper arboreum e Piper tuberculatum (Piperaceae)". No escopo de nossas pesquisas sobre agentes bioativos da flora brasileira, vinte e quatro extratos e frações de Piper arboreum Aub. e Piper tuberculatum Jacq. (Piperaceae) tiveram sua atividade tripanocida avaliada através do ensaio colorimétrico com MTT. As atividades mais potentes foram manifestadas pelas frações hexânicas das folhas de P. arboreum (CI 50 = 13,3 µg/mL) e P. tuberculatum (CI 50 = 17,2 µg/mL). As frações hexânicas dos frutos de P. tuberculatum e P. arboreum também apresentaram efeito tóxico potente contra as formas epimastigotas de Trypanosoma cruzi, com valores de CI 50 (µg/mL) de 32,2 e 31,3, respectivamente. Adicionalmente, o estudo fitoquímico da fração hexânica das folhas de P. arboreum forneceu duas amidas pirrolidínicas, piperilina (1) e 4,5-diidropiperilina (2), que podem ser responsáveis pela atividade antiprotozoária desta fração.Unitermos: Antiprotozoário, tripanocida, Piper arboreum, Piper tuberculatum, Piperaceae, Trypanosoma cruzi. ABSTRACT:In the scope of our ongoing research on bioactive agents from Brazilian flora, twenty-four extracts and fractions obtained from Piper arboreum Aub. and Piper tuberculatum Jacq. (Piperaceae) were screened for trypanocidal activity by using MTT colorimetric assay. The strongest activity was found in hexane fractions from the leaves of P. arboreum (IC 50 = 13.3 µg/ mL) and P. tuberculatum (IC 50 = 17.2 µg/mL). Hexane fractions of the fruits of P. tuberculatum and P. arboreum showed potent toxic effects on epimastigote forms of Trypanosoma cruzi, with values of IC 50 (µg/mL) of 32.2 and 31.3, respectively. Additionally, the phytochemical study of the hexane fraction of P. arboreum leaves furnished two pyrrolidine amides, piperyline (1) and 4,5-dihydropiperyline (2), which could be responsible, at least in part for the observed antiprotozoal activity.

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Section: Resultsmentioning

confidence: 99%

Trypanocidal activity of Piper arboreum and Piper tuberculatum (Piperaceae)

Regasini¹,

Cotinguiba²,

Passerini³

et al. 2009

Rev. bras. farmacogn.

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“…Whether or not these and/or additional residues are also required for the activity of piperine will therefore be an interesting piece of work for the future. The prevalence of a large number of natural and synthetic piperine analogues (Ribeiro et al, 2004) should also be of use in progressing such studies and may shed light on whether the 1,3-benzodioxole group or the increased rigidity or planarity of the piperine structure (cf. capsaicin) may underlie its pharmacological properties.…”

Section: Possible Sites Of Action Of Piperine On Trpv1mentioning

confidence: 99%

Effects of piperine, the pungent component of black pepper, at the human vanilloid receptor (TRPV1)

McNamara

Randall

Gunthorpe

2005

British J Pharmacology

266

186

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1 We have characterised the effects of piperine, a pungent alkaloid found in black pepper, on the human vanilloid receptor TRPV1 using whole-cell patch-clamp electrophysiology. 2 Piperine produced a clear agonist activity at the human TRPV1 receptor yielding rapidly activating whole-cell currents that were antagonised by the competitive TRPV1 antagonist capsazepine and the non-competitive TRPV1 blocker ruthenium red. 3 The current-voltage relationship of piperine-activated currents showed pronounced outward rectification (2574-fold between À70 and þ 70 mV) and a reversal potential of 0.070.4 mV, which was indistinguishable from that of the prototypical TRPV1 agonist capsaicin. 4 Although piperine was a less potent agonist (EC 50 ¼ 37.971.9 mM) than capsaicin (EC 50 ¼ 0.2970.05 mM), it demonstrated a much greater efficacy (approximately two-fold) at TRPV1. 5 This difference in efficacy did not appear to be related to the proton-mediated regulation of the receptor since a similar degree of potentiation was observed for responses evoked by piperine (230720%, n ¼ 11) or capsaicin (284732%, n ¼ 8) upon acidification to pH 6.5. 6 The effects of piperine upon receptor desensitisation were also unable to explain this effect since piperine resulted in more pronounced macroscopic desensitisation (t 1/2 ¼ 9.970.7 s) than capsaicin (t 1/2 420 s) and also caused greater tachyphylaxis in response to repetitive agonist applications. 7 Overall, our data suggest that the effects of piperine at human TRPV1 are similar to those of capsaicin except for its propensity to induce greater receptor desensitisation and, rather remarkably, exhibit a greater efficacy than capsaicin itself. These results may provide insight into the TRPV1-mediated effects of piperine on gastrointestinal function.

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“…A piperina foi testada contra epimastigotas e amastigotas do T. cruzi, demonstrando toxicidade dosedependente, com IC 50 de 7,36 μM para epimastigotas e IC 50 de 4,91 µM para amastigotas. Dessa maneira, a piperina demonstrou ser uma potente substância tripanossomicida, sendo mais tóxica para amastigotas intracelulares que para epimastigotas (Ribeiro et al, 2004) …”

Section: (Figura 5)unclassified

Substâncias da natureza com atividade anti-Trypanosoma cruzi

Saúde-Guimarães¹,

Faria²

2007

Rev. bras. farmacogn.

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RESUMO:A doença de Chagas, uma zoonose causada por Trypanosoma cruzi, afeta em todo o mundo cerca de 16 a 18 milhões de pessoas. Sua transmissão ocorre através das fezes de triatomíneos, insetos hematófagos conhecidos como barbeiro. Atualmente, a principal forma de transmissão da doença de Chagas em áreas urbanas é por meio de transfusão de sangue contaminado. A violeta de genciana é o único agente que pode ser empregado na quimioprofi laxia de sangue destinado à transfusão. No entanto, existem algumas restrições ao seu uso. A quimioterapia disponível para a doença de Chagas não é efi caz uma vez que as drogas disponíveis nifurtimox e benznidazol são ativas apenas na fase aguda da doença e apresentam sérios efeitos colaterais. Várias substâncias isoladas de plantas foram avaliadas como agentes anti-T. cruzi, objetivando encontrar drogas com menos efeitos colaterais e maior efi cácia para a quimioprofi laxia e quimioterapia da doença de Chagas. Nesta revisão são apresentadas as substâncias de origem natural com atividade anti-T. cruzi.

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Toxic Effects of Natural Piperine and Its Derivatives on Epimastigotes and Amastigotes of Trypanosoma cruzi.

Cited by 13 publications

References 1 publication

Trypanocidal activity of Piper arboreum and Piper tuberculatum (Piperaceae)

Trypanocidal activity of Piper arboreum and Piper tuberculatum (Piperaceae)

Effects of piperine, the pungent component of black pepper, at the human vanilloid receptor (TRPV1)

Substâncias da natureza com atividade anti-Trypanosoma cruzi

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