Activity of Neolignans Isolated from Piper regnellii (MIQ.) C. DC. var. pallescens (C. DC.) YUNCK against Trypanosoma cruzi

Luize, Patrícia Shima; Ueda-Nakamura, Tânia; Filho, Benedito Prado Dias; Cortez, Diógenes Aparı́cio Garcia; Nakamura, Celso Vataru

doi:10.1248/bpb.29.2126

Cited by 87 publications

(56 citation statements)

References 17 publications

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“…In this context, several secondary metabolites of different structural patterns have proven active against T. cruzi (Saúde- Guimarães & Faria, 2007), and screening of plant extracts is a valid strategy being exploited to discover trypanocidal agents (Leite et al, 2001;Takahashi et al, 2002;Luize et al, 2006;Pizzolatti et al, 2008).…”

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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“…Some previous studies have demonstrated the therapeutic potential of compounds derived from natural sources. 16,[48][49] Several synthetic compounds have also shown trypanocidal activity. 50,51 Acanthoic acid (1) at 3 µmol L -1 (the lowest concentration tested) displayed a growth inhibition of parasites of 13.6%, while at the highest concentration (331 µmol L -1 ), over 90% of the cells were affected.…”

Section: Biological Studiesmentioning

confidence: 99%

Acanthoic acid and other constituents from the stem of Annona amazonica (Annonaceae)

Pinheiro

Xavier

Souza

et al. 2009

J. Braz. Chem. Soc.

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O presente trabalho descreve o isolamento, a partir do caule de Annona amazonica, do ácido acantóico, um diterpeno do tipo pimaradieno que possui várias e importantes atividades biológicas descritas na literatura. Neste estudo foi verificado que este composto apresenta significante atividade tripanocida contra as formas epimastigotas de Trypanosoma cruzi. Também foi constatado que este diterpeno é o constituinte majoritário da planta, encontrado em cerca de 65% do extrato hexânico, demonstrando que A. amazonica é uma nova fonte natural renovável desta substância. Além do ácido acantóico, a investigação química resultou no isolamento dos alcalóides liriodenina e cassiticina, entre outros compostos, tais como terpenos, esteróides e ácidos graxos. Adicionalmente, é descrita a completa e inequívoca atribuição dos deslocamentos químicos de RMN de 1 H e 13 C da cassiticina.The present work reports the isolation of acanthoic acid, a promising pimaradiene-type diterpene with several important biological activities described in the literature, from the stems of Annona amazonica. We found that acanthoic acid has significant trypanocidal activity against the epimastigote forms of Trypanosoma cruzi. This diterpene is the major constituent of the plant, comprising at least 65% of the hexane extract, demonstrating that A. amazonica is a new renewable natural source for this compound. The chemical investigation also resulted in the isolation of the alkaloids liriodenine and cassythicine, and other compounds including terpenes, sterols, and fatty acids. Additionally, the complete and unequivocal 1 H and 13 C NMR chemical shift assignments for cassythicine are provided. Keywords: Annona amazonica, Annonaceae, acanthoic acid, cassythicine, trypanocidal activity IntroductionThe family Annonaceae, comprised of tropical and subtropical species with about 135 genera and more than 2500 species and widely distributed in South and Central America, Africa, Asia, and Australia, 1 is known for its edible fruits and the medicinal properties of several species. 2 In Brazil, there are 26 genera with about 260 species, including the genus Annona, which contains approximately 120 species. 3 Chemical investigations of species of Annonaceae have revealed their high chemical diversity in terms of secondary metabolites, such as alkaloids, acetogenins, terpenoids and lactones. These compounds have shown important biological activities, including antiparasitic, in particular against Leishmania sp., Plasmodium falciparum, and Trypanosoma cruzi. [4][5][6][7][8][9][10][11][12] Annona amazonica R.E. Fries is a tropical tree that grows up to 20-25 m tall and 35-60 cm in diameter, and is found from Panama to South America. In Brazil this species commonly occurs in the Amazon, mainly in the states of Amazonas and Pará. 13 To the best of our knowledge, only one previous phytochemical study has described the isolation and identification of cyanogenic constituents from this species. 14 Here we describe the isolation and structural identification of the chemica...

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“…The search of new drugs against leishmaniasis, potentially compounds and their derivatives have been described in the literature. [14][15][16] Neolignans are groups of compounds that show a wide range of biological effects including antifungal, [17][18][19] anti-schistosomal, [20][21][22][23] antiplasmodial, 24 trypanocidal, [25][26][27] antibacterial, 28 anti-PAF, 29,30 antipsychotic, 31 antioxidant, 32,33 activities, and biological activity against Escherichia coli,…”

Section: Introductionmentioning

confidence: 99%

Synthesis, X-ray crystal structure and theoretical calculations of antileishmanial neolignan analogues

Nascimento¹,

Santos²,

Santos³

et al. 2010

J. Braz. Chem. Soc.

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A síntese e a estrutura cristalina por difração de raios-X de dois análogos de neolignanas, 2-(4-clorofenil)-1-feniletanona (20) e 2-[tio(4-clorofenil)]-1-(3,4-dimetoxifenil)propan-1-ona (12) são descritas. O composto 12 apresenta atividade intracelular contra Leishmania donovani e Leishmania amazonensis de amastigotas que causam a leishmaniose tegumentar e visceral. Além disso, a teoria do funcional de densidade (DFT) com o funcional híbrido B3LYP foi empregado para calcular um conjunto de descritores moleculares para dezenove análogos sintéticos de neolignanas com atividades antileishmaniose. Posteriormente, a análise discriminante stepwise foi realizada para investigar possíveis relações entre a estrutura molecular e atividades biológicas. Por meio dessa análise os compostos foram classificados em dois grupos ativos e inativos de acordo com seu grau de atividade biológica, e as propriedades mais importantes foram as cargas de alguns átomos, a afinidade eletrônica e o ClogP.The synthesis and X-ray crystal diffraction structure of two analogues of neolignans, 2-(4-chlorophenyl)-1-phenylethanone (20) and 2-[(4-chlorophenyl)thio]-1-(3,4-dimethoxyphenyl) propan-1-one (12) is described. The compound 12 presents activity against intracellular Leishmania donovani and Leishmania amazonensis amastigotes that cause cutaneous and visceral leishmaniasis. In addition, the density functional theory (DFT) with the B3LYP hybrid functional was employed to calculate a set of molecular descriptors for nineteen synthetic analogues of neolignans with antileishmanial activities. Afterwards, the stepwise discriminant analysis was performed to investigate possible relationship between the molecular descriptors and biological activities. Through this analysis the compounds were classified into two groups active and inactive according to their degree of biological activities, and the more important properties were charges on some key atoms, electronic affinity and ClogP.

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Activity of Neolignans Isolated from Piper regnellii (MIQ.) C. DC. var. pallescens (C. DC.) YUNCK against Trypanosoma cruzi

Cited by 87 publications

References 17 publications

Trypanocidal activity of Piper arboreum and Piper tuberculatum (Piperaceae)

Trypanocidal activity of Piper arboreum and Piper tuberculatum (Piperaceae)

Acanthoic acid and other constituents from the stem of Annona amazonica (Annonaceae)

Synthesis, X-ray crystal structure and theoretical calculations of antileishmanial neolignan analogues

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