Benzoic acid derivatives from Piper species and their antiparasitic activity

Journal of Natural Products
Ninoska FloresIsabel L Bazzocchi

Abstract

Piper glabratum and P. acutifolium were analyzed for their content of main secondary constituents, affording nine new benzoic acid derivatives (1, 2, 4, 5, 7, and 10-13), in addition to four known compounds (3, 6, 8, and 9). Their structures were elucidated on the basis of spectroscopic data. Riguera ester reactions and optical rotation measurements established the new compounds as racemates. In the search for antiparasitic agents, the compounds were evaluated in vitro against the promastigote forms of Leishmania spp., Trypanosoma cruzi, and Plasmodium falciparum. Among the evaluated compounds, methyl 3,4-dihydroxy-5-(3'-methyl-2'-butenyl)benzoate (7) exhibited leishmanicidal effect (IC50 13.8-18.5 microg/mL) against the three Leishmania strains used, and methyl 3,4-dihydroxy-5-(2-hydroxy-3-methylbutenyl)benzoate (1), methyl 4-hydroxy-3-(2-hydroxy-3-methyl-3-butenyl)benzoate (3), and methyl 3,4-dihydroxy-5-(3-methyl-2-butenyl) benzoate (7) showed significant trypanocidal activity, with IC50 values of 16.4, 15.6, and 18.5 microg/mL, respectively.

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Mar 14, 2007·Planta medica·Ninoska FloresIsabel L Bazzocchi
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Citations

Dec 18, 2013·Fitoterapia·Xu-Jie QinXiao-Dong Luo
Aug 25, 2009·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ronan BatistaAlaíde Braga de Oliveira
Aug 8, 2014·Evidence-based Complementary and Alternative Medicine : ECAM·Thiago Bruno Lima PrandoArquimedes Gasparotto Junior
Oct 6, 2016·Phytotherapy Research : PTR·Nazif UllahMuhammad Hamayun
Nov 5, 2016·Parasitology International·Carlos Luan Alves PassosElvira Maria Saraiva
Jan 23, 2017·Journal of Ethnopharmacology·Lidiane Schultz BranquinhoArielle Cristina Arena
Apr 19, 2017·Pharmaceutical Biology·Keline Medeiros de Araújo-VilgesSelma Aparecida Souza Kuckelhaus
Feb 8, 2013·International Journal of Molecular Sciences·Dieudonné NdjonkaCarsten Wrenger
Feb 15, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Dominique F Moura do CarmoJefferson Rocha de Andrade Silva
Aug 10, 2021·Chemistry & Biodiversity·Yu-Xi ChenChuan-Rui Zhang
Sep 26, 2014·Chemical Reviews·Hidayat HussainSimon Gibbons

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