Antiparasitic activity of prenylated benzoic acid derivatives from Piper species

Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, Avda. Astrofísico, Francisco Sánchez 2, La Laguna, 38206 Tenerife, Canary Islands, Spain.
Phytochemistry (Impact Factor: 2.55). 05/2009; 70(5):621-7. DOI: 10.1016/j.phytochem.2009.03.010
Source: PubMed


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.

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    • "Although there are many reports on the phytochemistry of the genus Piper, we know of no previous study of the chemical constituents and antimycobacterial activity of P. diospyrifolium. Benzoic acid derivatives are frequently isolated from Piper species, and many of them exhibit diverse biological activities, such as antimicrobial, molluscicidal (Orjala et al., 1993), antifungal (Terreaux et al., 1998) and leishmanicidal (Flores et al., 2009). The conventional process for extraction of natural compounds used in medicine and industries is laborious, involving the use of large volumes of organic reagents that may cause deleterious environmental effects. "
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    ABSTRACT: The extraction by supercritical fluid (SFE-CO2) from leaves of Piper diospyrifolium and chromatographic column purification afforded the isolation of a new benzoic acid derivative 4-methoxy-3-[(E)-3-methyl-1,3-butadien-1-yl]-5-(3-methyl-2-buten-1-yl)-benzoic acid (1). The chemical structure was elucidated on the basis of spectroscopic methods and comparison with literature data. SFE-CO2 extracts and (1) were tested for their anti-Mycobacterium tuberculosis activities and cytotoxicities in J774G.8 macrophages. The compound (1) and SFE-CO2 extracts exhibited moderate activities against M. tuberculosis H37Rv with minimum inhibitory concentration (MIC) values of 125 μg/mL. The MIC values of M. tuberculosis clinical isolates ranged from 125 μg/mL to >250 μg/mL. The cytotoxicities results showed a selectivity index range from 0.6 to 1.0. Additional studies in structure activity-relationship as well as synergistic activity with antituberculous drugs should be conducted for a better evaluation of anti-mycobacterial activity of this compound.
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    • "Salicylic acid is a nonsteroidal anti-inflammatory agent which can behave as an apoptosis inducing agent in animal cancer cells; it can induce apoptosis and alter tumor glucose utilization (Sun and McKenna, 2011). Additionally, some prenylated para and meta hydroxybenzoic acid derivatives were found to exhibit significant antiparasitic activity (Flores et al., 2009), in addition to high antioxidant activity due to the presence of hydroxy groups at positions 3 and 4 (Yamagauchi et al., 2006). Significant successes have been achieved in many research areas including infectious diseases (bacteria, fungus, viruses) and metabolism of drugs. "
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    ABSTRACT: Series of new metronidazole urea and thiourea derivatives have been prepared in good yields through reactions of 2-(2-methyl-5-nitroimidazolyl)ethyl amine hydrochloride with various cyanates and isothiocyanates. Similarly, metronidazole salicylic acid derivatives were synthesized by reacting 2-(2-methyl-5-nitro-1H-imidazol-1-yl) ethyl 4-methyl benzene sulfonate (98) with meta and para hydroxy benzoic acids. Structures of the newly prepared compounds were confirmed through different spectroscopic methods such as 1H-NMR, 13C-NMR, mass spectrometry and also by elemental analyses. The antigiardial and antitrichomonal activities of the prepared compounds were evaluated in vitro. Compounds 3a, 3b, 3c, 6a, and 6b exhibited remarkable antigiardial activitiy and were found to be more active than metronidazole with IC50 of 6.4, 5.25, 5.36, 5.90, and 4.95 µg/mL, respectively, while compounds 3a, 3d, and 3g displayed the most antitrichomonal activity with IC50 of 6.3, 6.3, and 5.2 µg/mL, respectively.
    Full-text · Article · Aug 2014 · Medicinal Chemistry Research
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    • "In a continuation of our interest in the chemical and biological investigation of the family Apocynaceae [3] [4] [5] [6] [7] [8] [9], three new prenylbenzoic acid derivatives named formicinuoside A (1), formicinuoside B (2), formicinuoside C (3) together with five known compounds (4–8), were isolated from the stems of title species. In previous pharmacological work, prenylated benzoic acid derivatives have a range of biological activities, such as insecticidal [10], antifungal [11] [12] [13] [14] [15], antiparasitic [16] [17] [18], antibacterial [18] [19] [20]. Based on the traditional use of this plant, all the compounds were evaluated for their antibacterial activities against Staphylococcus aureus ATCC 25922, Pseudomonas aeruginosa ATCC 27853, Providensia smartii ATCC 29916 and Escherichia coli ATCC 11775. "

    Full-text · Dataset · Feb 2014
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