Antiparasitic activity of prenylated benzoic acid derivatives from Piper species

Esther Ninoska Flores Quisbert Flores Quisbert, Ignacio A. Jiménez, Alberto José Gimenez Turba, Grace Ruiz, David Gutiérrez, Genevieve Bourdy, Isabel L. Bazzocchi

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51 Scopus citations

Abstract

Fractionation of dichloromethane extracts from the leaves of Piper heterophyllum and P. aduncum afforded three prenylated hydroxybenzoic acids, 3-[(2E,6E,10E)-11-carboxy-3,7,15-trimethyl-2,6,10,14-hexadecatetraenyl)- 4,5-dihydroxybenzoic acid, 3-[(2E,6E,10E)-11-carboxy-13-hydroxy-3,7,15-trimethyl-2,6,10,14-hexadeca tetraenyl]-4,5-dihydroxybenzoic acid and 3-[(2E,6E,10E)-11-carboxy-14-hydroxy-3,7,15-trimethyl-2,6,10,15-hexadeca tetraenyl]-4,5-dihydroxybenzoic acid, along with the known compounds, 4,5-dihydroxy-3-(E,E,E-11-formyl-3,7,15-trimethyl-hexadeca-2,6,10,14-tet raenyl)benzoic acid (arieianal), 3,4-dihydroxy-5-(E,E,E-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraeny l)benzoic acid, 4-hydroxy-3-(E,E,E-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenyl)be nzoic acid, 3-(3,7-dimethyl-2,6-octadienyl)-4-methoxy-benzoic acid, 4-hydroxy-3-(3,7-dimethyl-2,6-octadienyl)benzoic acid and 4-hydroxy-3-(3-methyl-1-oxo-2-butenyl)-5-(3-methyl-2-butenyl)benzoic acid. Their structures were elucidated on the basis of spectroscopic data, including homo- and heteronuclear correlation NMR experiments (COSY, HSQC and HMBC) and comparison with data reported in the literature. Riguera ester reactions and optical rotation measurements established the compounds as racemates. The antiparasitic activity of the compounds were tested against three strains of Leishmania spp., Trypanosoma cruzi and Plasmodium falciparum. The results showed that 3-(3,7-dimethyl-2,6-octadienyl)-4-methoxy-benzoic acid exhibited potent and selective activity against L. braziliensis (IC50 6.5 μg/ml), higher that pentamidine used as control. Moreover, 3-[(2E,6E,10E)-11-carboxy-3,7,15-trimethyl- 2,6,10,14-hexadecatetraenyl)-4,5-dihydroxybenzoic acid and 4-hydroxy-3-(3-methyl-1-oxo-2-butenyl)-5-(3-methyl-2-butenyl)benzoic acid showed moderate antiplasmodial (IC50 3.2 μg/ml) and trypanocidal (16.5 μg/ml) activities, respectively.

Original languageEnglish
Pages (from-to)621-627
Number of pages7
JournalPhytochemistry
Volume70
Issue number5
DOIs
StatePublished - Mar 2009

Bibliographical note

Funding Information:
This investigation was supported by International Foundation of Sciences (Sweden, Grant F/3408-1), DGCYT (CTQ2006-13376/BQU), Program of Swedish Cooperation (UMSA-SIDA/TB-BRC, ASD91) and PCI-Iberoamérica (A/010794/07, AECI) projects. International collaboration was supported by project X.5 “Búsqueda, Obtención y Evaluación de Nuevos Agentes Antiparasitarios” CYTED (Iberoamerican Program of Science and Technology for Development, Subprogram X).

Keywords

  • Antiplasmodial
  • Leishmanicidal
  • P. aduncum
  • Piper heterophyllum
  • Prenylated benzoic acids
  • Trypanocidal

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