Benzoic Acid Derivatives from Piper Species and Their Fungitoxic Activity against Cladosporium cladosporioides and C. sphaerospermum

Lago, João Henrique G.; Ramos, Clécio S.; Casanova, Diego Campos C.; Morandim, Andréia de A.; Bergamo, Débora Cristina B.; Cavalheiro, Alberto José; Bolzani, Vanderlan S.; Furlan, Maysa; Guimarães, Elsie Franklin; Young, Maria Cláudia Marx; Kato, Massuo Jorge

doi:10.1021/np030530j

Cited by 191 publications

(153 citation statements)

References 27 publications

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“…Phytochemical investigations of Piper species have led to the identification of typical classes of compounds such as amides, terpenes, benzoic acid derivatives, carotenes, and hydroquinones in addition to lignans, neolignans and a few alkaloids (Navickiene et al, 2000;Silva et al, 2002;Lago et al, 2004;Navickiene et al, 2006;Potzernheim et al, 2006;Regasini et al, 2008;Continguiba et al, 2009).…”

Section: Introductionmentioning

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: Introductionmentioning

confidence: 99%

Trypanocidal activity of Piper arboreum and Piper tuberculatum (Piperaceae)

Regasini¹,

Cotinguiba²,

Passerini³

et al. 2009

Rev. bras. farmacogn.

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“…Studies of Piper species have revealed the presence of several classes of secondary metabolites, 1 including alkaloids, amides, 2-6 chromenes, 7,8 neolignans, 9 lignans, terpenes, 10,11 benzoic acid derivatives 12,13 and kavalactones.…”

Section: Introductionmentioning

confidence: 99%

Kavalactones and Benzoic Acid Derivatives from Leaves of Piper fuligineum Kunth (Piperaceae)

Mazzeu¹,

Felippe²,

Cotinguiba³

et al. 2017

J. Braz. Chem. Soc.

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The known kavalactones (E)-4-methoxy-6-styryl-2H-pyran-2-one, 4-methoxy-6-(3-phenyloxiran-2-yl)-2H-pyran-2-one, 6-(1,2-dihydroxy-2-phenylethyl)-4-methoxy-2H-pyran-2-one, the three benzoic acid derivatives methyl-4-methoxy-3-(3'-methyl-2'-butenyl)benzoate and methyl 2,2-dimethyl-4-oxochroman-6-carboxylate, and a new methyl 4-methoxy-3-(3-methylbut-2-enoyl)benzoate were isolated from the ethanolic extract of Piper fuligineum. The structures of these compounds were determined by using a combination of spectroscopic methods, including 1D-and 2D-nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry. This is the first report of the chemical study of P. fuligineum, and the methyl 4-methoxy-3-(3-methylbut-2-enoyl)benzoate is described as a new natural product.

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“…Local communities have traditionally used this species as an anesthetic sedative for toothache, antidote for snake bite, stimulants, and stomach problems (Chaves et al, 2003). Recent studies showed that different extracts and isolated molecules from P. tuberculatum present antifungal (Lago et al, 2004), antitumor (Bezerra et al, 2006), antiplatelet aggregation (Fontenele et al, 2009), insecticide (Pohlit et al, 2004) and hypotensive properties (Duarte et al, 2004).…”

Section: Introductionmentioning

confidence: 99%

Antileishmanial activity of 3-(3,4,5-trimethoxyphenyl) propanoic acid purified from Amazonian Piper tuberculatum Jacq., Piperaceae, fruits

Ferreira¹,

Kayano²,

Silva³

et al. 2010

Rev. bras. farmacogn.

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RESUMO: "Atividade antileishmania do 3,4,5-trimetoxi-dihidrocinâmico purificado das frutas de Piper tuberculatum Jacq., Piperaceae, amazônica". A atividade leishmanicida do ácido 3,4,5-trimetoxi-dihidrocinâmico (TMPP) isolado do extrato hidroalcoólico de frutos de Piper turbeculatum Jacq. amazônica foi testado em ensaios in vitro utilizando formas promastigotas de Leishmania amazonensis. O TMPP foi utilizado em culturas de L. amazonensis nas concentrações de 1600 a 6,25 µg/mL. A viabilidade celular das formas promastigotas foi observada em 24, 48, 72 e 96 h para cálculo da CI50. O TMPP apresentou efeito leishmanicida dose dependente para as formas promastigotas de L. amazonensis apresentando CI50 de 145 µg/mL. Unitermos:Piper tuberculatum Jacq., Piperaceae, ácido 3,4,5-trimetoxi-dihidrocinâmico, Leishmania amazonensis, atividade leishmanicida.ABSTRACT: Leishmanicidal activity of the 3-(3,4,5-trimethoxyphenyl) propanoic acid (TMPP) isolated from EtOH extracts of the Amazonian Piper turbeculatum Jacq. fruits was evaluated in vitro using Leishmania amazonensis promastigotes. The TMPP was assayed at concentrations of 1600 to 6.25 µg/mL for 24, 48, 72 and 96 h. Promastigotes viability was analyzed and the IC50 of TMPP was 145 µg/mL.

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Benzoic Acid Derivatives from Piper Species and Their Fungitoxic Activity against Cladosporium cladosporioides and C. sphaerospermum

Cited by 191 publications

References 27 publications

Trypanocidal activity of Piper arboreum and Piper tuberculatum (Piperaceae)

Trypanocidal activity of Piper arboreum and Piper tuberculatum (Piperaceae)

Kavalactones and Benzoic Acid Derivatives from Leaves of Piper fuligineum Kunth (Piperaceae)

Antileishmanial activity of 3-(3,4,5-trimethoxyphenyl) propanoic acid purified from Amazonian Piper tuberculatum Jacq., Piperaceae, fruits

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