Rosangela Laurentiz | Universidade Estadual Paulista "Júlio de Mesquita Filho" (original) (raw)
Papers by Rosangela Laurentiz
Synlett
The reaction of phenols or aryl ethers with tetronic acid mediated by BF3·OMe2 was investigated. ... more The reaction of phenols or aryl ethers with tetronic acid mediated by BF3·OMe2 was investigated. This strategy allowed for the preparation of β-(hydroxyaryl)butenolides and β-arylbutenolides in a single step in a simpler way than previously reported synthetic methods
Experimental Parasitology
Complete assignments of 1 H and 13 C NMR spectral data for 7,7′-dihydroarylnaphthalene lignan lac... more Complete assignments of 1 H and 13 C NMR spectral data for 7,7′-dihydroarylnaphthalene lignan lactones
Complete assignments of 1 H and 13 C NMR spectral data for 7,7′-dihydroarylnaphthalene lignan lac... more Complete assignments of 1 H and 13 C NMR spectral data for 7,7′-dihydroarylnaphthalene lignan lactones
... Carlos Alemán,* Paulo Marcos Donate, Rosangela da Silva, and Gil Valdo José da Silva .... more ... Carlos Alemán,* Paulo Marcos Donate, Rosangela da Silva, and Gil Valdo José da Silva . Departament ... 2) (a) During, JR; Wertz, DW J. Chem. Phys.1968, 49, 2118. (b) Cremer, D.; Pople, JA J. Am. Chem. Soc.1975, 97, 1358. ...
Methylenedioxybenzyl)-γ-butyrolactone (MDBL) and (-)-hinokinin (HK) were obtained by partial synt... more Methylenedioxybenzyl)-γ-butyrolactone (MDBL) and (-)-hinokinin (HK) were obtained by partial synthesis and characterized by 1 H NMR and computational methods (conformational analysis, molecular modeling, structural data mining and chemometrics). Three conformers were detected for MDBL and nine were found for HK. The energy differences are around 1 and 2 kcal mol-1 and rotation barriers are less than 3 and 5 kcal mol-1 for MDBL and HK conformers, respectively. The geometries of these conformers, obtained from semiempirical PM3 and density functional theory (DFT) B3LYP 6-31G** calculations agree satisfactorily with 1 H NMR data (vicinal proton-proton coupling constants) and structures retrieved from the Cambridge Structural Database (torsion angles). DFT combined with some variants of the Haasnoot-de Leeuuw-Altona equations gives the best predictions for the coupling constants. The molecular conformation of MDBL, of HK, and of related systems depends not only on intramolecular interactions but also on crystal packing forces and solvent-solute interactions, in particular hydrogen bonds and polar interactions. Hydration favors more stable HK conformers, which can be important for their behavior in chemical and biological systems.
Medicinal Chemistry Research
A series of lactone 1,4-dihydroquinoline derivatives 4 (4 and 4aa-4cm) was screened for in vitro ... more A series of lactone 1,4-dihydroquinoline derivatives 4 (4 and 4aa-4cm) was screened for in vitro antileishmanial activity against the promastigote form of Leishmania (Leishmania) amazonensis. Screening results indicate that all of the synthesized compounds significantly reduced the growth of promastigote forms of promastigotes of L. (L.) amazonensis. The cytotoxicity of the most active compounds was also measured on peritoneal macrophage cells. Compounds 4ah and 4bn showed better activities than other derivatives with IC 50 values of 6.22 and 9.05 μM, respectively, with selectivity index 22 and 15 times less toxicity to macrophages cells than to parasites, respectively. The experimental data propose that the compounds may be further investigated against amastigote forms and may contribute to the search of new candidates drugs for treatment of cutaneous leishmaniasis.
Medicinal Chemistry Research
In this work, a series of lactone 1,4-dihydroquinoline derivatives 4 were efficiently synthesized... more In this work, a series of lactone 1,4-dihydroquinoline derivatives 4 were efficiently synthesized and characterized by 1 H and 13 C NMR. The synthesized compounds were evaluated for their in vitro antibacterial activity against the bacterial strains Porphyromonas gingivalis, Prevotella nigrescens, Streptococcus mitis, and Streptococcus sanguinis and against Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium kansasii. The results revealed that the evaluated compounds were more active against Gram negative bacteria. Compounds 4ba, 4bb, 4bg, 4bi, 4bn, 4ch, and 4ci displayed moderate antibacterial activity against P. gingivalis. 4bi was the most active compound against the three strains of Mycobacterium. Based on structure-activity relationship studies, we observed that the presence of a nitro group on the benzylic ring and a methylenedioxy group on the dihydroquinoline ring enhanced the antibacterial activity of the derivatives. Keywords Azo-heterocyclic compounds • quinoline derivatives • antibacterial activity
Chemistry & biodiversity, Jan 18, 2018
Six dibenzylbutyrolactonic lignans ((-)-hinokinin (1), (-)-cubebin (2), (-)-yatein (3), (-)-5-met... more Six dibenzylbutyrolactonic lignans ((-)-hinokinin (1), (-)-cubebin (2), (-)-yatein (3), (-)-5-methoxy-yatein (4), dihydrocubebin (5) and dihydroclusin (6)) were isolated from Piper cubeba seed extract and evaluated against Schistosoma mansoni. All lignans, except 5, were able to separate the adult worm pairs and reduce the egg numbers during the 24 h of incubation. Lignans 1, 3 and 4 (containing a lactone ring) were the most efficient concerning anti-parasitary activity. Comparing structures 3 and 4, the presence of the methoxy group at position 5 appears to be important for this activity. Considering 1 and 3, it is possible to see that the substitution pattern change (methylenedioxy or methoxyl groups) in positions 3' and 4' alter the biological response, with 1 being the second most active compound. Computational calculations suggest that the activity of compound 4 can be correlated with the largest lipophilicity value.
International Journal of Veterinary Science and Medicine
Grape pomace obtained as a byproduct of industrial processing of grapes retains nutrients and sub... more Grape pomace obtained as a byproduct of industrial processing of grapes retains nutrients and substances with anthelmintic potential such as saponins, tannins, and flavonoids. Therefore, this study evaluated the in vitro ovicidal and larvicidal activity of hydroalcoholic grape pomace extract against gastrointestinal nematodes of sheep. The anthelmintic evaluation was performed by in vitro assays with eggs and larvae of nematodes obtained from naturally infected donor sheep. The grape pomace extract showed high in vitro ovicidal and larvicidal activity with LD 50 values of 0.30 mg/mL for egg hatching inhibition, 1.01 mg/mL for larval development inhibition and 100% efficacy in larval migration inhibition assays at all concentrations evaluated. The effect of tannins was evaluated by the addition of 50 mg/mL polyvinyl polypyrrolidone to grape pomace extract at the concentration of 12.5 mg/mL. The in vitro ovicidal activity of grape pomace was reduced by only 15% after polyvinyl polypyrrolidone addition, indicating that other phytochemicals also contribute to the ovicidal activity displayed by the extract. Our results demonstrate that grape pomace exhibits in vitro anthelmintic activity, suggesting that, beyond its nutritional potential, this pomace can also be an ally for gastrointestinal nematode control in sheep.
Molecular informatics, 2018
Encouraged by the anti-inflammatory activity of hinokinin in vivo, which is also observed for the... more Encouraged by the anti-inflammatory activity of hinokinin in vivo, which is also observed for the analogues dinitrohinokinin and diidrocubebin, herein we used in vitro and in silico methods to assess their selectivity profiles and predict their binding modes with Cyclooxygenases (COX-1 and 2). The in vitro assays demonstrated dinitrohinokinin is about 13 times more selective for COX-2 than for COX-1, a similar profile observed for the drugs celecoxib (selective index ≈9) and meloxicam (selective index ≈11). Predictions of the binding modes suggested dinitrohinokinin interacts with COX-2 very similarly to rofecoxib, exploring residues at the hydrophilic pocket of the enzyme that accessible to ligands only in this isoform. This lignan also interacts with COX-1 in a similar mode to meloxicam, blocking the access of the substrate to the catalytic cleft. Therefore, dinitrohinokinin is a promising lead for the design of selective COX-2 inhibitors.
ChemistryOpen, 2018
Lignans are a large class of natural products that have been isolated from many plants. They reve... more Lignans are a large class of natural products that have been isolated from many plants. They reveal diverse biological activities, especially antiviral and antitumor properties. From , lignans of several classes can be isolated from the roots, rhizomes, stems, leaves, seeds, and fruits. Among its various chemical constituents, (-)-cubebin and (-)-hinokinin are found in significant quantities. Although they have been known for some time, during the last few decades their biological properties have been studied by several research groups. The cubebins have been identified as a lactol monomer and dimers as a mixture of diastereoisomers. Recently, their structural characterization and the synthesis of the possible structures have led to the correction of some earlier structural proposals. This review describes the more recent developments in the study of the medicinal attributes of cubebin and hinokinin extracted from and the synthesis and biological testing of some analogues.
Synthetic Communications
An efficient, catalyst-free, microwave-assisted approach has been developed for the synthesis of ... more An efficient, catalyst-free, microwave-assisted approach has been developed for the synthesis of 4-azo-butyenolides derivatives by condensing tetronic acid with various anilines. This approach exhibited good functional group compatibility and produced the desired products in good to excellent yields in just 30-40 min. This approach can be seen as a better alternative to protocols with long reaction times used for the synthesis of these compounds, which are synthons for the obtaining of quinolines.
Revista Virtual de Química, 2017
The (-)-cubebin is a lignan dibenzylbutyrolactolic of occurrence in various species of plants, es... more The (-)-cubebin is a lignan dibenzylbutyrolactolic of occurrence in various species of plants, especially in the genus Piper. Although it has been known for over 150 years, the last few decades the biological properties of this molecule has attracted the attention of several research groups. Recent publications obtained from Scopus bases, SciFinder and PubMed database have highlighted the numerous biological activities attributed to cubebin, as trypanocidal activity, shistomicida, cytotoxicity on cancer lines, vasodilator, antihistaminic, and anti-inflammatory. These studies demonstrate the pharmacological potential of cubebin and its importance as starting material to obtain even more potent derivatives.
Pesquisa Veterinária Brasileira, 2016
RESUMO: Dois experimentos foram realizados com o objetivo de avaliar o uso das sementes secas de ... more RESUMO: Dois experimentos foram realizados com o objetivo de avaliar o uso das sementes secas de Piper cubeba nas dietas de frangos de corte de 1 a 21 dias de idades e seus efeitos sobre o perfil bioquímicos do sangue e na biometria dos órgãos das aves. Em cada experimento 240 pintos de corte machos, com um dia de idade da linhagem Cobb foram distribuídos em um delineamento inteiramente casualizado, com cinco tratamentos e quatro repetições de 12 aves por parcela experimental. No primeiro experimento foi avaliado o uso da Piper cubeba em dietas consideradas de alta digestibilidade, a base de milho e farelo de soja, e no segundo avaliou-se o uso da pimenta em dietas de baixa digestibilidade, as quais foram obtidas com a inclusão de farinha de carne e ossos. Com relação aos dados de perfil bioquímico sanguíneo do experimento I, com exceção da gama glutamil transferase, todos os demais níveis séricos se apresentaram dentro dos limites recomendados para aves, e apenas os níveis de trigl...
Bioorganic & medicinal chemistry letters, Jan 15, 2017
(À)-Cubebin (CUB), isolated from seeds of Piper cubeba, was used as starting material to obtain t... more (À)-Cubebin (CUB), isolated from seeds of Piper cubeba, was used as starting material to obtain the derivatives (À)-hinokinin (HK) and (À)-O-benzyl cubebin (OBZ). Using paw edema as the experimental model and different chemical mediators (prostaglandin and dextran), it was observed that both derivatives were active in comparison with both negative (5% Tween Ò 80 in saline) and positive (indomethacin) controls. The highest reduction in the prostaglandin-induced edema was achieved by OBZ (66.0%), while HK caused a 59.2% reduction. Nonetheless, the dextran-induced paw edema was not significantly reduced by either of the derivatives (HK or OBZ), which inhibited edema formation by 18.3% and 3.5%, respectively, in contrast with the positive control, cyproheptadine, which reduced the edema by 56.0%. The docking analysis showed that OBZ presented the most stable ligand-receptor (COX-2-cyclooxygenase-2) interaction in comparison with CUB and HK.
Veterinary Parasitology, 2016
This study describes the in vitro anthelmintic activity of extracts from Opuntia ficus indica aga... more This study describes the in vitro anthelmintic activity of extracts from Opuntia ficus indica against gastrointestinal nematodes of sheep. The anthelmintic activity was evaluated by inhibition of egg hatching, larval development and larval migration assays. The residual aqueous fractions from cladodes and fruits showed higher ovicidal activity with EC 50 values of 7.2 mg/mL and 1.5 mg/mL, respectively. The aqueous, hexane, and ethyl acetate fractions from fruits and the aqueous fraction from cladodes inhibited 100% of larval development at the lowest concentration tested (1.56 mg/mL). The crude cladode and fruit ethanolic extracts inhibited larval migration and showed EC 50 values of 0.74 mg/mL and 0.27 mg/mL, respectively. Phytochemical screening detected high concentrations of alkaloids, tannins, flavonoids, and saponins in the fruits and cladodes. The results demonstrated that O. ficus exhibits anthelmintic activity in vitro, suggesting that, beyond its nutritional potential, this plant can also be an ally for parasite control in sheep.
Synlett
The reaction of phenols or aryl ethers with tetronic acid mediated by BF3·OMe2 was investigated. ... more The reaction of phenols or aryl ethers with tetronic acid mediated by BF3·OMe2 was investigated. This strategy allowed for the preparation of β-(hydroxyaryl)butenolides and β-arylbutenolides in a single step in a simpler way than previously reported synthetic methods
Experimental Parasitology
Complete assignments of 1 H and 13 C NMR spectral data for 7,7′-dihydroarylnaphthalene lignan lac... more Complete assignments of 1 H and 13 C NMR spectral data for 7,7′-dihydroarylnaphthalene lignan lactones
Complete assignments of 1 H and 13 C NMR spectral data for 7,7′-dihydroarylnaphthalene lignan lac... more Complete assignments of 1 H and 13 C NMR spectral data for 7,7′-dihydroarylnaphthalene lignan lactones
... Carlos Alemán,* Paulo Marcos Donate, Rosangela da Silva, and Gil Valdo José da Silva .... more ... Carlos Alemán,* Paulo Marcos Donate, Rosangela da Silva, and Gil Valdo José da Silva . Departament ... 2) (a) During, JR; Wertz, DW J. Chem. Phys.1968, 49, 2118. (b) Cremer, D.; Pople, JA J. Am. Chem. Soc.1975, 97, 1358. ...
Methylenedioxybenzyl)-γ-butyrolactone (MDBL) and (-)-hinokinin (HK) were obtained by partial synt... more Methylenedioxybenzyl)-γ-butyrolactone (MDBL) and (-)-hinokinin (HK) were obtained by partial synthesis and characterized by 1 H NMR and computational methods (conformational analysis, molecular modeling, structural data mining and chemometrics). Three conformers were detected for MDBL and nine were found for HK. The energy differences are around 1 and 2 kcal mol-1 and rotation barriers are less than 3 and 5 kcal mol-1 for MDBL and HK conformers, respectively. The geometries of these conformers, obtained from semiempirical PM3 and density functional theory (DFT) B3LYP 6-31G** calculations agree satisfactorily with 1 H NMR data (vicinal proton-proton coupling constants) and structures retrieved from the Cambridge Structural Database (torsion angles). DFT combined with some variants of the Haasnoot-de Leeuuw-Altona equations gives the best predictions for the coupling constants. The molecular conformation of MDBL, of HK, and of related systems depends not only on intramolecular interactions but also on crystal packing forces and solvent-solute interactions, in particular hydrogen bonds and polar interactions. Hydration favors more stable HK conformers, which can be important for their behavior in chemical and biological systems.
Medicinal Chemistry Research
A series of lactone 1,4-dihydroquinoline derivatives 4 (4 and 4aa-4cm) was screened for in vitro ... more A series of lactone 1,4-dihydroquinoline derivatives 4 (4 and 4aa-4cm) was screened for in vitro antileishmanial activity against the promastigote form of Leishmania (Leishmania) amazonensis. Screening results indicate that all of the synthesized compounds significantly reduced the growth of promastigote forms of promastigotes of L. (L.) amazonensis. The cytotoxicity of the most active compounds was also measured on peritoneal macrophage cells. Compounds 4ah and 4bn showed better activities than other derivatives with IC 50 values of 6.22 and 9.05 μM, respectively, with selectivity index 22 and 15 times less toxicity to macrophages cells than to parasites, respectively. The experimental data propose that the compounds may be further investigated against amastigote forms and may contribute to the search of new candidates drugs for treatment of cutaneous leishmaniasis.
Medicinal Chemistry Research
In this work, a series of lactone 1,4-dihydroquinoline derivatives 4 were efficiently synthesized... more In this work, a series of lactone 1,4-dihydroquinoline derivatives 4 were efficiently synthesized and characterized by 1 H and 13 C NMR. The synthesized compounds were evaluated for their in vitro antibacterial activity against the bacterial strains Porphyromonas gingivalis, Prevotella nigrescens, Streptococcus mitis, and Streptococcus sanguinis and against Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium kansasii. The results revealed that the evaluated compounds were more active against Gram negative bacteria. Compounds 4ba, 4bb, 4bg, 4bi, 4bn, 4ch, and 4ci displayed moderate antibacterial activity against P. gingivalis. 4bi was the most active compound against the three strains of Mycobacterium. Based on structure-activity relationship studies, we observed that the presence of a nitro group on the benzylic ring and a methylenedioxy group on the dihydroquinoline ring enhanced the antibacterial activity of the derivatives. Keywords Azo-heterocyclic compounds • quinoline derivatives • antibacterial activity
Chemistry & biodiversity, Jan 18, 2018
Six dibenzylbutyrolactonic lignans ((-)-hinokinin (1), (-)-cubebin (2), (-)-yatein (3), (-)-5-met... more Six dibenzylbutyrolactonic lignans ((-)-hinokinin (1), (-)-cubebin (2), (-)-yatein (3), (-)-5-methoxy-yatein (4), dihydrocubebin (5) and dihydroclusin (6)) were isolated from Piper cubeba seed extract and evaluated against Schistosoma mansoni. All lignans, except 5, were able to separate the adult worm pairs and reduce the egg numbers during the 24 h of incubation. Lignans 1, 3 and 4 (containing a lactone ring) were the most efficient concerning anti-parasitary activity. Comparing structures 3 and 4, the presence of the methoxy group at position 5 appears to be important for this activity. Considering 1 and 3, it is possible to see that the substitution pattern change (methylenedioxy or methoxyl groups) in positions 3' and 4' alter the biological response, with 1 being the second most active compound. Computational calculations suggest that the activity of compound 4 can be correlated with the largest lipophilicity value.
International Journal of Veterinary Science and Medicine
Grape pomace obtained as a byproduct of industrial processing of grapes retains nutrients and sub... more Grape pomace obtained as a byproduct of industrial processing of grapes retains nutrients and substances with anthelmintic potential such as saponins, tannins, and flavonoids. Therefore, this study evaluated the in vitro ovicidal and larvicidal activity of hydroalcoholic grape pomace extract against gastrointestinal nematodes of sheep. The anthelmintic evaluation was performed by in vitro assays with eggs and larvae of nematodes obtained from naturally infected donor sheep. The grape pomace extract showed high in vitro ovicidal and larvicidal activity with LD 50 values of 0.30 mg/mL for egg hatching inhibition, 1.01 mg/mL for larval development inhibition and 100% efficacy in larval migration inhibition assays at all concentrations evaluated. The effect of tannins was evaluated by the addition of 50 mg/mL polyvinyl polypyrrolidone to grape pomace extract at the concentration of 12.5 mg/mL. The in vitro ovicidal activity of grape pomace was reduced by only 15% after polyvinyl polypyrrolidone addition, indicating that other phytochemicals also contribute to the ovicidal activity displayed by the extract. Our results demonstrate that grape pomace exhibits in vitro anthelmintic activity, suggesting that, beyond its nutritional potential, this pomace can also be an ally for gastrointestinal nematode control in sheep.
Molecular informatics, 2018
Encouraged by the anti-inflammatory activity of hinokinin in vivo, which is also observed for the... more Encouraged by the anti-inflammatory activity of hinokinin in vivo, which is also observed for the analogues dinitrohinokinin and diidrocubebin, herein we used in vitro and in silico methods to assess their selectivity profiles and predict their binding modes with Cyclooxygenases (COX-1 and 2). The in vitro assays demonstrated dinitrohinokinin is about 13 times more selective for COX-2 than for COX-1, a similar profile observed for the drugs celecoxib (selective index ≈9) and meloxicam (selective index ≈11). Predictions of the binding modes suggested dinitrohinokinin interacts with COX-2 very similarly to rofecoxib, exploring residues at the hydrophilic pocket of the enzyme that accessible to ligands only in this isoform. This lignan also interacts with COX-1 in a similar mode to meloxicam, blocking the access of the substrate to the catalytic cleft. Therefore, dinitrohinokinin is a promising lead for the design of selective COX-2 inhibitors.
ChemistryOpen, 2018
Lignans are a large class of natural products that have been isolated from many plants. They reve... more Lignans are a large class of natural products that have been isolated from many plants. They reveal diverse biological activities, especially antiviral and antitumor properties. From , lignans of several classes can be isolated from the roots, rhizomes, stems, leaves, seeds, and fruits. Among its various chemical constituents, (-)-cubebin and (-)-hinokinin are found in significant quantities. Although they have been known for some time, during the last few decades their biological properties have been studied by several research groups. The cubebins have been identified as a lactol monomer and dimers as a mixture of diastereoisomers. Recently, their structural characterization and the synthesis of the possible structures have led to the correction of some earlier structural proposals. This review describes the more recent developments in the study of the medicinal attributes of cubebin and hinokinin extracted from and the synthesis and biological testing of some analogues.
Synthetic Communications
An efficient, catalyst-free, microwave-assisted approach has been developed for the synthesis of ... more An efficient, catalyst-free, microwave-assisted approach has been developed for the synthesis of 4-azo-butyenolides derivatives by condensing tetronic acid with various anilines. This approach exhibited good functional group compatibility and produced the desired products in good to excellent yields in just 30-40 min. This approach can be seen as a better alternative to protocols with long reaction times used for the synthesis of these compounds, which are synthons for the obtaining of quinolines.
Revista Virtual de Química, 2017
The (-)-cubebin is a lignan dibenzylbutyrolactolic of occurrence in various species of plants, es... more The (-)-cubebin is a lignan dibenzylbutyrolactolic of occurrence in various species of plants, especially in the genus Piper. Although it has been known for over 150 years, the last few decades the biological properties of this molecule has attracted the attention of several research groups. Recent publications obtained from Scopus bases, SciFinder and PubMed database have highlighted the numerous biological activities attributed to cubebin, as trypanocidal activity, shistomicida, cytotoxicity on cancer lines, vasodilator, antihistaminic, and anti-inflammatory. These studies demonstrate the pharmacological potential of cubebin and its importance as starting material to obtain even more potent derivatives.
Pesquisa Veterinária Brasileira, 2016
RESUMO: Dois experimentos foram realizados com o objetivo de avaliar o uso das sementes secas de ... more RESUMO: Dois experimentos foram realizados com o objetivo de avaliar o uso das sementes secas de Piper cubeba nas dietas de frangos de corte de 1 a 21 dias de idades e seus efeitos sobre o perfil bioquímicos do sangue e na biometria dos órgãos das aves. Em cada experimento 240 pintos de corte machos, com um dia de idade da linhagem Cobb foram distribuídos em um delineamento inteiramente casualizado, com cinco tratamentos e quatro repetições de 12 aves por parcela experimental. No primeiro experimento foi avaliado o uso da Piper cubeba em dietas consideradas de alta digestibilidade, a base de milho e farelo de soja, e no segundo avaliou-se o uso da pimenta em dietas de baixa digestibilidade, as quais foram obtidas com a inclusão de farinha de carne e ossos. Com relação aos dados de perfil bioquímico sanguíneo do experimento I, com exceção da gama glutamil transferase, todos os demais níveis séricos se apresentaram dentro dos limites recomendados para aves, e apenas os níveis de trigl...
Bioorganic & medicinal chemistry letters, Jan 15, 2017
(À)-Cubebin (CUB), isolated from seeds of Piper cubeba, was used as starting material to obtain t... more (À)-Cubebin (CUB), isolated from seeds of Piper cubeba, was used as starting material to obtain the derivatives (À)-hinokinin (HK) and (À)-O-benzyl cubebin (OBZ). Using paw edema as the experimental model and different chemical mediators (prostaglandin and dextran), it was observed that both derivatives were active in comparison with both negative (5% Tween Ò 80 in saline) and positive (indomethacin) controls. The highest reduction in the prostaglandin-induced edema was achieved by OBZ (66.0%), while HK caused a 59.2% reduction. Nonetheless, the dextran-induced paw edema was not significantly reduced by either of the derivatives (HK or OBZ), which inhibited edema formation by 18.3% and 3.5%, respectively, in contrast with the positive control, cyproheptadine, which reduced the edema by 56.0%. The docking analysis showed that OBZ presented the most stable ligand-receptor (COX-2-cyclooxygenase-2) interaction in comparison with CUB and HK.
Veterinary Parasitology, 2016
This study describes the in vitro anthelmintic activity of extracts from Opuntia ficus indica aga... more This study describes the in vitro anthelmintic activity of extracts from Opuntia ficus indica against gastrointestinal nematodes of sheep. The anthelmintic activity was evaluated by inhibition of egg hatching, larval development and larval migration assays. The residual aqueous fractions from cladodes and fruits showed higher ovicidal activity with EC 50 values of 7.2 mg/mL and 1.5 mg/mL, respectively. The aqueous, hexane, and ethyl acetate fractions from fruits and the aqueous fraction from cladodes inhibited 100% of larval development at the lowest concentration tested (1.56 mg/mL). The crude cladode and fruit ethanolic extracts inhibited larval migration and showed EC 50 values of 0.74 mg/mL and 0.27 mg/mL, respectively. Phytochemical screening detected high concentrations of alkaloids, tannins, flavonoids, and saponins in the fruits and cladodes. The results demonstrated that O. ficus exhibits anthelmintic activity in vitro, suggesting that, beyond its nutritional potential, this plant can also be an ally for parasite control in sheep.