RESUMO
Chemical investigation of the aerial parts (except fruits and calixes) of Physalis nicandroides var. attenuata led to the isolation of a series of new labdane-type diterpenoids, including the closely related compounds 1-3, the labdane glucosides 4 and 5, a mixture of the epimeric alcohols 6 and 7, and one labdanetriol, isolated as its tri-O-acetyl derivative 9. In addition, three new withanolides (14-16) and six known compounds were isolated. The structures of these compounds were elucidated by analysis of their spectroscopic data and chemical transformations, and those of compounds 1, 4, and 16 were confirmed by X-ray diffraction analysis of the natural product (1) and of the corresponding acetyl derivatives 4a and 16a. Fourteen of these compounds were assayed for their in vitro inhibitory activity against yeast α-glucosidase and acetylcholinesterase enzymes. The results were negative in both cases, except for compound 3a that marginally inhibited the activity of acetylcholinesterase with an IC50 value of 64.4 µM.
Assuntos
Diterpenos/isolamento & purificação , Physalis/química , Vitanolídeos/isolamento & purificação , Cristalografia por Raios X , Estrutura Molecular , Análise Espectral/métodosRESUMO
The chemical study of Ageratina deltoidea afforded grandiflorenic acid (1), ent-kaurenoic acid (2), and eight benzylbenzoates (3 - 10), two of them, 3,5-dimethoxybenzyl 2,3,6-trimethoxybenzoate (5) and 4-(ß-d-glucopyranosyloxy)-3-hydroxybenzyl 2,6-dimethoxybenzoate (9), described for the first time. In addition, the new sesquiterpene lactone deltoidin C (13), together with the known 11 and 12, the phenolic compounds: ayanin, 2,6-dimethoxybenzoic acid, methyl 3,4-dihydroxycinnamate, chlorogenic acid, and 3,5-dicaffeoylquinic acid were also isolated. The structures of these compounds were determined by spectroscopic methods and chemical reactions. The antibacterial and antifungal activities of compounds 1 - 12 were evaluated on Staphylococcus aureus, Escherichia coli, and Candida albicans. Deltoidin A (11) was the most active antibacterial agent (MIC 16.0 µg ml-1 ) against E. coli, and the ent-kaurenoid derivatives (1 - 2) showed activity (MIC 31.0 µg ml-1 ) against S. aureus.
Assuntos
Ageratina/química , Antibacterianos/farmacologia , Antifúngicos/farmacologia , Componentes Aéreos da Planta/química , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antifúngicos/química , Antifúngicos/isolamento & purificação , Candida albicans/efeitos dos fármacos , Relação Dose-Resposta a Droga , Escherichia coli/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Conformação Molecular , Staphylococcus aureus/efeitos dos fármacos , Relação Estrutura-AtividadeRESUMO
The phytochemical study of the aerial parts of Melampodium perfoliatum afforded six melampolides (1, 3, 5-8), a eudesmanolide (9), two diterpene lactones (10, 11), and two ent-kaurane derivatives (12, 13), together with the known melampodin (2) and polymatin A (4). The structures of the compounds were elucidated by physical data analysis and chemical reactions. Compounds 2, 4, 5, and 10 exhibited dose-dependent anti-inflammatory activity on the 12-O-tetradecanoylphorbol-13-acetate-induced ear edema model, with ID50 values of 1.14, 0.56, 1.15, and 1.49 µmol/ear, respectively, compared to the reference compound indomethacin (0.24 µmol/ear).
Assuntos
Asteraceae/química , Terpenos/isolamento & purificação , Animais , Anti-Inflamatórios/farmacologia , Relação Dose-Resposta a Droga , Edema/induzido quimicamente , Indometacina/farmacologia , Concentração Inibidora 50 , Lactonas/química , Lactonas/isolamento & purificação , Lactonas/farmacologia , México , Camundongos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Componentes Aéreos da Planta/química , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Terpenos/química , Terpenos/farmacologia , Acetato de Tetradecanoilforbol/farmacologiaRESUMO
A mixture of the new epimeric labdenetriols 1 and 2 was isolated from the aerial parts of Physalis nicandroides. The structures of 1 and 2, including their absolute configurations, were established by analyses of their spectroscopic data, together with the X-ray diffraction analysis of acetonide 3 and chemical correlation with (-)-(13E)-labd-13-ene-8α,15-diol (6), whose absolute configuration was also confirmed by X-ray analysis of its dibromo derivative 7. The epimeric labdenediols 8 and 9, the known labdanes 6 and 11, and the acylsucroses 12 and 13 were also isolated. Labdanes 6 and 11 showed moderate anti-inflammatory activities in the induced ear edema model.
Assuntos
Anti-Inflamatórios não Esteroides/isolamento & purificação , Diterpenos/química , Diterpenos/isolamento & purificação , Physalis/química , Animais , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/farmacologia , Cristalografia por Raios X , Modelos Animais de Doenças , Diterpenos/farmacologia , Orelha/patologia , Edema/induzido quimicamente , Masculino , México , Camundongos , Conformação Molecular , Estrutura Molecular , Componentes Aéreos da Planta/química , EstereoisomerismoRESUMO
The phytochemical study of Pittocaulon filare afforded three oplopanes (1-3), a eudesmane (6), and three oplopane glucosides (7-9), one of them reported as its acetyl derivative (7a), together with several known compounds. The structures of the compounds were elucidated by spectroscopic analysis and chemical reactions. The anti-inflammatory activity of compounds 1-5 was determined using the 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced ear edema model, and the effect of compounds 1-4 on the recruitment of neutrophils was evaluated using the myeloperoxidase test. Compounds 1 and 2 were the more active anti-inflammatory agents, with lower ID50 values (0.17 and 0.18 µmol/ear, respectively) than indomethacin (0.24 µmol/ear), but they had a lesser effect on the inhibition of neutrophil infiltration than both indomethacin and compound 3, indicating that the tested compounds do not have the same ability to inhibit edema and to prevent cell infiltration.
Assuntos
Asteraceae/química , Sesquiterpenos/isolamento & purificação , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Modelos Animais de Doenças , Edema/induzido quimicamente , Edema/tratamento farmacológico , Glucosídeos/efeitos adversos , Glucosídeos/uso terapêutico , Indometacina/efeitos adversos , Indometacina/uso terapêutico , México , Infiltração de Neutrófilos/efeitos dos fármacos , Neutrófilos/metabolismo , Ressonância Magnética Nuclear Biomolecular , Peroxidase/metabolismo , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Estereoisomerismo , Acetato de Tetradecanoilforbol/farmacologiaRESUMO
Two seco-eremophiladiolides, velatumolide and epi-velatumolide, the trihydroxyfuranoeremophilane velatumin, and three eremophilane glucosides were isolated from Pittocaulon velatum, together with several known compounds. The structures of these compounds were elucidated by spectroscopic analysis and chemical reactions. The anti-inflammatory activity of the isolated compounds was investigated using the TPA-induced ear edema model.
Assuntos
Anti-Inflamatórios/isolamento & purificação , Asteraceae/química , Flavonoides/isolamento & purificação , Glucosídeos/isolamento & purificação , Sesquiterpenos/isolamento & purificação , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Modelos Animais de Doenças , Edema/induzido quimicamente , Edema/tratamento farmacológico , Flavonoides/química , Flavonoides/farmacologia , Glucosídeos/química , Glucosídeos/farmacologia , México , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Acetato de Tetradecanoilforbol/farmacologiaRESUMO
Two new withanolides, philadelphicalactone C (1) and philadelphicalactone D (4), along with the known withaphysacarpin (3), ixocarpanolide (5), philadelphicalactone A (6), and ixocarpalactone A (7) were isolated from the aerial parts of Physalis philadelphica Lam. Structures of these compounds were determined by spectroscopic analyses and that of philadelphicalactone C (1) was confirmed by X-ray crystallographic analysis. Evaluation of the cytotoxic activity of all isolates and the derivative 2 against a panel of human cancer cell lines indicated a potent activity of compounds 2, 3, 6, and 7.
Assuntos
Antineoplásicos/química , Antineoplásicos/farmacologia , Lactonas/química , Lactonas/farmacologia , Physalis/química , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Humanos , Concentração Inibidora 50 , Lactonas/isolamento & purificaçãoRESUMO
Eight new compounds, labdanes 2-4, homoergostane 10, and sucrose esters 12-15, were isolated from aerial parts of Physalis sordida together with several known compounds. Structures of the new compounds were elucidated using spectroscopic evidence and chemical transformations. The structure of 10 was confirmed by X-ray crystallographic analysis of its methyl ester. Anti-inflammatory activity of compounds 1, 2, 4, 5, and 12-15 was evaluated using the TPA-induced mouse ear edema test. Compounds 12 (IC(50) 0.26 mumol/ear) and 15 (IC(50) 0.24 mumol/ear) showed anti-inflammatory activity similar to that of indomethacin (IC(50) 0.24 mumol/ear).
Assuntos
Anti-Inflamatórios não Esteroides/isolamento & purificação , Diterpenos/isolamento & purificação , Physalis/química , Sacarose/análogos & derivados , Sacarose/isolamento & purificação , Animais , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/farmacologia , Cristalografia por Raios X , Diterpenos/química , Diterpenos/farmacologia , Edema/induzido quimicamente , Edema/tratamento farmacológico , Ésteres , Camundongos , Conformação Molecular , Estrutura Molecular , Sacarose/química , Sacarose/farmacologia , Acetato de Tetradecanoilforbol/farmacologiaRESUMO
The new eremophilanolide 1, the known eremophilane derivatives 2 and 3, already described as part of mixtures, the known compounds hyperin, 2''-acetylhyperin and two calenduladiol esters were isolated from Roldana lineolata. Their structures were determined by spectroscopic methods. Compounds 1 and 2 as well as their acetylated and oxidized derivatives were tested against several fungi strains. Eremophilanolide 1 showed a mild activity against Trichophyton mentagrophytes.
Assuntos
Antifúngicos/farmacologia , Asteraceae/química , Extratos Vegetais/farmacologia , Triterpenos/farmacologia , Antifúngicos/química , Antifúngicos/isolamento & purificação , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Trichophyton/efeitos dos fármacos , Triterpenos/química , Triterpenos/isolamento & purificaçãoRESUMO
Four new modified eremophilanes, angulifolide (1) and angulifolins A-C (2-4), and two new triacetylglucosides (7 and 8) were isolated from Roldana angulifolia, together with several known compounds. The structures of the new compounds were elucidated by spectroscopic analysis and chemical reactions. The absolute configuration of compounds 2 and 3 was established by Mosher ester methodology. Cytotoxicity against selected human cancer cell lines was determined for the more abundant isolated metabolites.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Asteraceae/química , Glucosídeos/isolamento & purificação , Plantas Medicinais/química , Sesquiterpenos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Glucosídeos/química , Glucosídeos/farmacologia , Humanos , México , Estrutura Molecular , Sesquiterpenos/química , Sesquiterpenos/farmacologiaRESUMO
Eight new eremophilanolides (1, 2, 4-7, 9, and 10), a new eremophilane (13), and several known compounds were isolated from the roots and aerial parts of Senecio mairetianus. The chemical structures were proposed taking into consideration spectroscopic analyses and chemical transformations. X-ray diffraction analysis of 2, 4, and 9 confirmed their structures. The stereochemistry of 1,10-epoxy-8alpha-methoxyermophilanolide (3) was determined. Compounds 4-7, 9, and 10 are possible artifacts obtained by preparation of the alkaloidal extract.
Assuntos
Naftalenos/química , Naftalenos/isolamento & purificação , Plantas Medicinais/química , Senécio/química , Cristalografia por Raios X , México , Conformação Molecular , Estrutura Molecular , Raízes de Plantas/química , Sesquiterpenos Policíclicos , SesquiterpenosRESUMO
Aerial parts of Physalis coztomatl afforded a new labdane diterpene, physacoztomatin (1), and five new withanolides, physacoztolides A-E (5-9). Six known compounds were also isolated. The structures of the new compounds were established after analyses of their spectroscopic data and by means of chemical transformations. X-ray diffraction analyses of 15-dehydrophysacoztomatin (2) and 5 confirmed the structures of 1 and 5. Labd-13(E)-ene-8alpha,15-diol (4) and physacoztomatin (1) represent the first labdane diterpenes isolated from the genus Physalis.
Assuntos
Diterpenos/isolamento & purificação , Ergosterol/análogos & derivados , Ergosterol/isolamento & purificação , Physalis/química , Plantas Medicinais/química , Cristalografia por Raios X , Diterpenos/química , Ergosterol/química , Ergosterol/farmacologia , México , Conformação Molecular , Estrutura MolecularRESUMO
A phytochemical study of Robinsonecio gerberifolius afforded six new sesquiterpenoids, two oplopane (1and 2) and four eremophilane derivatives (3-6). The structures of these compounds were elucidated on spectroscopic grounds, and the absolute configurations of compounds 3 and 4 were established from CD analysis. The known 3beta-angeloyloxy-1,10-epoxyfuranoeremophilane (7) was also isolated, and its stereochemistry was revised. The cytotoxic activities of compounds 1-7 were determined against five human cancer cell lines.