Antiparasitic activity of prenylated benzoic acid derivatives from Piper species
| Autor: | Alberto Giménez, Ignacio A. Jiménez, Grace Ruiz, David Gutiérrez, Ninoska Flores, Isabel L. Bazzocchi, Geneviève Bourdy |
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| Rok vydání: | 2009 |
| Předmět: |
EXTRACTION
Spectrometry Mass Electrospray Ionization Hydroxybenzoic acid Magnetic Resonance Spectroscopy PLANTE MEDICINALE Stereochemistry Antiparasitic medicine.drug_class Chemical structure Plant Science Horticulture Benzoates Biochemistry chemistry.chemical_compound Species Specificity LEISHMANIOSE EVALUATION medicine PARASITE EFFICACITE Molecular Biology Dichloromethane Benzoic acid Piper ACTIVITE BIOLOGIQUE Antiparasitic Agents biology SPECTROSCOPIE General Medicine PALUDISME ACIDE BENZOIQUE Piperaceae biology.organism_classification STRUCTURE CHIMIQUE Plant Leaves chemistry Heteronuclear molecule MALADIE DE CHAGAS LUTTE ETUDE EXPERIMENTALE CHROMATOGRAPHIE Chromatography Liquid |
| Zdroj: | Phytochemistry. 70:621-627 |
| ISSN: | 0031-9422 |
| Popis: | 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-hexadecatetraenyl]-4,5-dihydroxybenzoic acid and 3-[(2E,6E,10E)-11-carboxy-14-hydroxy-3,7,15-trimethyl-2,6,10,15-hexadecatetraenyl]-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-tetraenyl)benzoic acid (arieianal), 3,4-dihydroxy-5-(E,E,E-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenyl)benzoic acid, 4-hydroxy-3-(E,E,E-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenyl)benzoic 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 (IC(50) 6.5 microg/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 (IC(50) 3.2 microg/ml) and trypanocidal (16.5 microg/ml) activities, respectively. |
| Databáze: | OpenAIRE |
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