RESUMO
ETHNOPHARMACOLOGICAL RELEVANCE: An investigation of topical anti-inflammatory activity was undertaken on plants used in Central America traditional medicine. AIM OF STUDY: Four herbal drugs used in the folk medicine of Central America to treat inflammatory skin affections (Acacia cornigera bark, Byrsonima crassifolia bark, Sphagneticola trilobata leaves and Sweetia panamensis bark) were evaluated for their topical anti-inflammatory activity. MATERIALS AND METHODS: Petroleum ether, chloroform and methanol extracts were obtained for herbal medicines and then extracts were tested on Croton oil-induced ear dermatitis model in mice. RESULTS: Almost all the extracts reduced the Croton oil-induced ear dermatitis in mice and the chloroform ones showed the highest activity, with ID(50) (dose giving 50% oedema inhibition) values ranging from 112 microg/cm(2) (Byrsonima crassifolia) to 183 microg/cm(2) (Sphagneticola trilobata). As reference, ID(50) of the non-steroidal anti-inflammatory drug indomethacin was 93 microg/cm(2). CONCLUSIONS: Lipophilic extracts from these species can be regarded as potential sources of anti-inflammatory principles.
Assuntos
Anti-Inflamatórios/uso terapêutico , Asteraceae , Dermatite/tratamento farmacológico , Fabaceae , Malpighiaceae , Fitoterapia , Extratos Vegetais/uso terapêutico , Administração Tópica , Animais , Anti-Inflamatórios/farmacologia , Óleo de Cróton , Dermatite/etiologia , Indometacina/farmacologia , Indometacina/uso terapêutico , Camundongos , Casca de Planta , Extratos Vegetais/farmacologia , Folhas de Planta , Pele/efeitos dos fármacosRESUMO
The two main classes of secondary metabolites, alkaloids and quinovic acid glycosides, of Uncaria tomentosa (Willd.) DC. (Rubiaceae), a Peruvian plant commonly known as 'uña de gato', have been analysed. Separation of the alkaloidal fraction was achieved using a solid phase extraction method based on cationic exchange, and an analytical method employing HPLC-ES/MS has been developed. Quantitative data for commercial wild bark, cultivated bark and leaves are reported. The analysis of quinovic acid glycosides was performed directly on the crude extract using both a fast analytical method based on flow injection ES/MS, and a more complete analytical technique using HPLC-MS.
Assuntos
Alcaloides/isolamento & purificação , Unha-de-Gato/química , Glicosídeos/isolamento & purificação , Triterpenos/isolamento & purificação , Cromatografia Líquida de Alta Pressão/métodos , Peru , Casca de Planta/química , Folhas de Planta/química , Plantas Medicinais/química , Espectrometria de Massas por Ionização por Electrospray/métodosRESUMO
Leiothrix (Eriocaulaceae) é um gênero exclusivo da América do Sul, com 37 espécies restritas ao Brasil. Leiothrix flavescens (Bong.) Ruhland e Leiothrix curvifolia (Bong.) Ruhland, são espécies endêmicas em áreas dos Estados de Minas Gerais e Bahia. Existem na literatura poucos estudos químicos e biológicos realizados com espécies desse gênero. Neste trabalho, foi estudada a atividade antioxidante pelo ensaio TEAC (Trolox Equivalent Antioxidant Capacity) e de autoxidação, utilizando ácido linoléico, de xantonas isoladas dos extratos etanólicos de L. curvifolia e L. flavescens. As substâncias apresentaram moderada atividade antioxidante, quando comparadas com padrões de quercetina e de BHT (2, 6 - ditercbutil - 4 - metóxifenil).
Leiothrix (Eriocaulaceae) is an exclusively South American genus of which 37 species are restricted to Brazil. Leiothrix flavescens (Bong.) Ruhland and Leiothrix curvifolia (Bong.) Ruhland, are species endemic to areas of Minas Gerais and Bahia States. Chemical and biological investigations of this genus are scarse. The objective of this work was to investigate the antioxidant effect using TEAC and linoleic acid assays of the xanthones isolated from the ethanolic extract of these species. These substances showed a moderate antioxidant activity when compared to quercetin and to BHT.
RESUMO
Hexane, chloroform and methanol extracts of seven herbal drugs used in the folk medicine of Central America against skin disorders (Aristolochia trilobata leaves and bark, Bursera simaruba bark, Hamelia patens leaves, Piper amalago leaves, and Syngonium podophyllum leaves and bark) were evaluated for their topical anti-inflammatory activity against the Croton oil-induced ear oedema in mice. Most of the extracts induced a dose-dependent oedema reduction. The chloroform extract of almost all the drugs exhibited interesting activities with ID(50) values ranging between 108 and 498 micro g/cm(2), comparable to that of indomethacin (93 micro g/cm(2)). Therefore, the tested plants are promising sources of principles with high anti-inflammatory activity.
Assuntos
Anti-Inflamatórios/uso terapêutico , Preparações de Plantas/uso terapêutico , Administração Tópica , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , América Central , Relação Dose-Resposta a Droga , Avaliação Pré-Clínica de Medicamentos/métodos , Edema/induzido quimicamente , Edema/tratamento farmacológico , Camundongos , Casca de Planta , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Extratos Vegetais/uso terapêutico , Folhas de Planta , Preparações de Plantas/isolamento & purificação , Preparações de Plantas/farmacologiaRESUMO
Two new sesquiterpene lactones: 8alpha-(4'-acetoxymethacryloyloxy)-3alpha,9beta-dihydroxy-1(10)E,4Z,11(13)-germacratrien-12,6alpha-olide (1) and 8alpha-(2'E)-(2'-acetoxymethyl-2'-butenoyloxy)-3alpha,9beta-dihydroxy-1(10)E,4Z,11(13)-germacratrien-12,6alphaolide (2), together with the known zoapatanolide A were isolated from the aerial parts of Montanoa tomentosa Cerv. in La Llave et Lex ssp. microcephala (Sch. Bip. In K. Koch) V.A. Funk (Asteraceae). The structures of all compounds were established on the basis of 1D, 2D NMR, and EIMS analysis.
Assuntos
Asteraceae/química , Lactonas/isolamento & purificação , Oxepinas/isolamento & purificação , Sesquiterpenos de Germacrano , Sesquiterpenos/isolamento & purificação , Abortivos não Esteroides/química , Abortivos não Esteroides/isolamento & purificação , Feminino , Humanos , Lactonas/química , Espectroscopia de Ressonância Magnética , Medicina Tradicional , México , Estrutura Molecular , Montanoa , Oxepinas/química , Sesquiterpenos/químicaRESUMO
Aqueous infusions of Brazilian Maytenus leaves are used as beverages, foodstuffs, and phytomedicines. Previously, we isolated two new flavonoid tetrasaccharides from the infusion of Maytenus aquifolium leaves that showed antiulcer activity. In this investigation a new flavonoid tetrasaccharide, kaempferol-3-O-alpha-L-rhamnopyranosyl (1-->6)-O-[alpha-L-arabinopyranosyl (1-->3)-O-alpha-L-rhamnopyranosyl (1-->2)]-O-beta-D-galactopyranoside (3), was isolated, together with kaempferol tri- and disaccharides and quercetin trisaccharides from the aqueous infusion of Maytenus ilicifolia leaves. All structures were elucidated by ES-MS and NMR spectroscopic methods. The quantitative analysis of the flavonoid glycosides from Maytenus ilicifolia and M. aquifolium has been performed by HPLC.
Assuntos
Bebidas/análise , Flavonoides/química , Flavonoides/isolamento & purificação , Glicosídeos/química , Glicosídeos/isolamento & purificação , Brasil , Cromatografia Líquida de Alta Pressão/métodos , Cromatografia Gasosa-Espectrometria de Massas , Folhas de Planta/químicaRESUMO
A new cyclohexenone (1) and a new caffeoyl ester derivative (2), together with the known compounds (-)-isolariciresinol 3-alpha-O-beta-D-glucopyranoside (3), (+)-1-hydroxypinoresinol 1-O-beta-D-glucopyranoside (4), isoacteoside (5), luteolin 4'-O-beta-D-glucopyranoside (6), and indole-3-carboxylic acid (7), were isolated from the leaves of Bauhinia tarapotensis. The structures of these new compounds were determined by spectroscopic data analysis. The antioxidant activities of 1-7 were determined by measuring their free radical scavenging effects, using the 1,1-diphenyl-2-dipicrylhydrazyl free radical (DPPH) and Trolox equivalent antioxidant activity (TEAC) methods, and the coupled oxidation of beta-carotene and linoleic acid. Compounds 3-5 showed good activities in the DPPH and TEAC tests, while compounds 1 and 2 were active in the coupled oxidation of beta-carotene and linoleic acid bioassay.
Assuntos
Antioxidantes/isolamento & purificação , Bepridil/análogos & derivados , Ácidos Cafeicos/isolamento & purificação , Cicloexanonas/isolamento & purificação , Fabaceae/química , Sequestradores de Radicais Livres/isolamento & purificação , Glucosídeos/isolamento & purificação , Luteolina , Fenóis , Picratos , Plantas Medicinais/química , Antioxidantes/química , Antioxidantes/farmacologia , Benzotiazóis , Bepridil/farmacologia , Compostos de Bifenilo , Ácidos Cafeicos/química , Ácidos Cafeicos/farmacologia , Cromanos/farmacologia , Cromatografia Líquida de Alta Pressão , Cicloexanonas/química , Cicloexanonas/farmacologia , Equador , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/farmacologia , Glucosídeos/química , Glucosídeos/farmacologia , Indóis/química , Indóis/isolamento & purificação , Indóis/farmacologia , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Folhas de Planta/química , Ácidos Sulfônicos/químicaRESUMO
A tautomeric pair of new isoprenylated benzophenones, aristophenone A (1a) and B (1b), have been isolated from Garcinia aristata fruits. Their structures has been determined using high-field 2D NMR techniques.
Assuntos
Benzofenonas/isolamento & purificação , Plantas Medicinais/química , Benzofenonas/química , Cromatografia Líquida de Alta Pressão , Cuba , Frutas/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular , EstereoisomerismoRESUMO
Three new naphthopyranone glycosides, paepalantine-9-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (1), paepalantine-9-O-alpha-L-arabinopyranosyl-(1-->6)-beta-D-glucopyranoside (2), and paepalantine-9-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (3), along with the known paepalantine-9-O-beta-D-glucopyranoside (4) were isolated from aerial parts of Paepalanthus microphyllus. These compounds were characterized by spectrometric methods, including electrospray mass spectrometry and 1D and 2D NMR experiments. As a part of our program for screening natural compounds for anti-HIV activity, compounds 1-4 were tested in C8166 cells infected with HIV-1MN.
Assuntos
Fármacos Anti-HIV/química , Glicosídeos/química , Plantas Medicinais/química , Fármacos Anti-HIV/isolamento & purificação , Fármacos Anti-HIV/farmacologia , Brasil , Avaliação Pré-Clínica de Medicamentos , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , HIV-1/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Espectrometria de Massas por Ionização por Electrospray , Espectrofotometria UltravioletaRESUMO
8-Carboxymethyl-1,6-dihydroxy-3,5-dimethoxyxanthone, 8-carboxymethyl-1,5,6-trihydroxy-3-methoxyxanthone and 8-carboxymethyl-1,3,5,6-tetrahydroxyxanthone were isolated from the capitula of Leiothrix curvifolia and Leiothrix flavescens and characterized by spectroscopic methods, mainly 1D and 2D NMR experiments, as well as by electrospray mass spectrometry. Eight known flavonoids were also isolated and they were identified by 1D and 2D NMR experiments and comparison with literature data.
Assuntos
Flavonoides/isolamento & purificação , Magnoliopsida/química , Xantenos/isolamento & purificação , Xantonas , Flavonoides/química , Espectroscopia de Ressonância Magnética , Xantenos/químicaRESUMO
A new naphthopyranone dimer (1) named planifolin was isolated from a methylene chloride extract of the capitula of Paepalanthus planifolius. The structure of 1 has been determined by chemical and spectroscopic means. In addition, a known dihydronaphthopyranone glycoside and seven known flavonoids were isolated from an ethanolic extract of the leaves of P. planifolius.
Assuntos
Flavonoides/química , Naftóis/química , Plantas Medicinais/química , Pironas/química , Cromatografia em Camada Fina , Flavonoides/isolamento & purificação , Espectroscopia de Ressonância Magnética , Naftóis/isolamento & purificação , Extratos Vegetais/química , Folhas de Planta/química , Pironas/isolamento & purificação , Espectrofotometria Infravermelho , Espectrofotometria UltravioletaRESUMO
The isolation of nine triterpenoid saponins (1-9), among them six new natural compounds (1-6), from the MeOH extract of the fruits of Cyclanthera pedata is reported. All of the structures were elucidated by spectroscopic methods, including the concerted application of one-dimensional (1)H-(1)H total correlation spectroscopy, (1)H-(1)H nuclear Overhauser effect spectroscopy), and (13)C-(13)C DEPT-NMR and two-dimensional NMR techniques (double-quantum filtered correlated spectroscopy, rotating-frame Overhauser enhancement spectroscopy, heteronuclear single quantum coherence, and heteronuclear multiple bond correlation). A comparative study of seeds and fruits has been also carried out.
Assuntos
Frutas/química , Saponinas/química , Triterpenos/química , Cromatografia Gasosa-Espectrometria de Massas , Modelos Químicos , PeruRESUMO
Droplet countercurrent chromatography and high-performance liquid chromatography fractionation of the aqueous infusion from Maytenus aquifolium Martius leaves afforded two flavonoid tetrasaccharides: quercetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-O-[beta-D-glucopyranosyl(1-->3)-O- alpha-L-rhamnopyranosyl(1-->2)-O-beta-D-galactopyranoside and kaempferol 3-O-alpha-L-rhamnopyranosyl(1-->6)-O-[beta-D-glucopyranosyl(1-->3)-O- alpha-L-rhamnopyranosyl(1-->2)-O-beta-D-galactopyranoside. All structures were elucidated by spectroscopic methods. Pharmacological essays of the infusion showed antiulcer activity in rats.
Assuntos
Antiulcerosos/isolamento & purificação , Antiulcerosos/farmacologia , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Quempferóis , Oligossacarídeos/isolamento & purificação , Plantas Medicinais/química , Quercetina/análogos & derivados , Animais , Antiulcerosos/química , Brasil , Flavonoides/química , Cromatografia Gasosa-Espectrometria de Massas , Espectroscopia de Ressonância Magnética , Masculino , Oligossacarídeos/química , Oligossacarídeos/farmacologia , Folhas de Planta/química , Quercetina/química , Quercetina/isolamento & purificação , Quercetina/farmacologia , Ratos , Ratos Wistar , Espectrofotometria Ultravioleta , Úlcera Gástrica/etiologia , Úlcera Gástrica/prevenção & controle , Estresse Psicológico/fisiopatologiaRESUMO
Three new compounds-3, 4-dihydro-10-hydroxy-7-methoxy-3-(R)-methyl-1H-3,4-dihydronaphtho- ]2, 3c]-pyran-1-one-9-O-beta-D-glucopyranoside (1), 3, 4-dihydro-10-hydroxy-7-methoxy-3-(R)-methyl-1H-3,4-dihydronaphtho- [2, 3c]-pyran-1-one-9-O-beta-D-glucopyranosyl-(1-->6)-glucopyranoside (2), and 3,4-dihydro-10-dihydroxy-7-methoxy-3-(R)-methyl-1H-3, 4-dihydronaphtho-[2,3c]-pyran-1-one-9-O-beta-D-allopyranosyl (1-->6)glucopyranoside (3)-were isolated from the leaves of Paepalanthus vellozioides and Paepalanthus latipes and characterized by spectrometric methods, mainly electrospray mass spectrometry and 1D and 2D NMR experiments. These unusual glycosylated dihydronaphthopyranones may serve as taxonomic markers of the genus Paepalanthus, since these compounds were not detected in other genera belonging to the Eriocaulaceae family.
Assuntos
Glicosídeos/química , Plantas Medicinais/química , Brasil , Cromatografia Líquida de Alta Pressão , Dicroísmo Circular , Hidrólise , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Espectrofotometria UltravioletaRESUMO
Five new flavonol 7-O-glycosides (1-5), having quercetin or quercetin 3-methyl ether as their aglycons, and sugar chains made up of three or four sugars, including beta-D-glucopyranose, alpha-L-rhamnopyranose, and beta-D-xylopyranose, have been isolated from the aerial parts of Bidens andicola, along with a new chalcone ester glycoside (6) and five known chalcone ester glycosides. The structures of 1-6 were elucidated using a combination of spectroscopic techniques.
Assuntos
Flavonoides/química , Inibidores do Crescimento/química , Plantas Medicinais/química , Sequência de Carboidratos , Cromatografia Líquida de Alta Pressão , Flavonoides/isolamento & purificação , Glicosídeos/química , Glicosídeos/isolamento & purificação , Inibidores do Crescimento/isolamento & purificação , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Peru , Extratos Vegetais/química , Folhas de Planta/química , Espectrometria de Massas de Bombardeamento Rápido de Átomos , Espectrofotometria UltravioletaRESUMO
The present study examines the effects of the extracts [petroleum ether, CHCl3, CHCl3/MeOH (9:1) and MeOH], partially purified fractions and pure compounds from Guettarda acreana on the electrically induced contractions (E.C.I.) of the isolated guinea-pig ileum. The results of the experiments indicate that CHCl3/MeOH (9:1), MeOH extract, and the MeOH soluble part from CHCl3/MeOH extract tested at concentrations of 1.2, 2.5, and 5 micrograms/ml, dose-dependently reduced the guinea-pig ileum contractions. Furthermore, some partially purified fractions I-IV from the MeOH extract, each tested at the same concentrations of the extracts, and some pure compounds (6 x 10(-6), 3 x 10(-6), 1 x 10(-6) M) isolated from the above fractions significantly reduced, in a dose-dependent manner, the electrical contractions of the ileum. The active compounds were identified as the known indole alkaloids strictosidic acid, lyalosidic acid, 5 alpha-carboxystrictosidine, strictosidine, and sickingine, as well as the known quinic acid derivatives 5-caffeoylquinic acid, 4,5-dicaffeoylquinic acid, and shikimic acid by spectral data. Two known quinovic acid glycosides and a new triterpenic glycoside, quinovic acid 3 beta-O-alpha-rhamnopyranosyl-(1-->3)-(beta-glucopyranosyl-(1-->6)-beta- glucopyranoside, were also isolated and their structures established by NMR and M5 data.
Assuntos
Extratos Vegetais/farmacologia , Folhas de Planta/química , Plantas Medicinais/química , Animais , Estimulação Elétrica , Cobaias , Íleo/efeitos dos fármacos , Íleo/fisiologia , Técnicas In Vitro , Espectroscopia de Ressonância Magnética , Masculino , Estrutura Molecular , Extratos Vegetais/química , Espectrometria de Massas de Bombardeamento Rápido de ÁtomosRESUMO
The MeOH extract of the aerial parts of Croton ruizianus afforded two new pregnane glycosides 1 and 2, together with the morphinandienone alkaloids flavinantine (3) and O-methylflavinantine (4). Their structures were elucidated by NMR experiments including 1H-1H (1D TOCSY and 2D DQF-COSY) and 1H-13C (HSQC, HMBC) spectroscopy. The proaggregating activity of the MeOH extract and the isolates were evaluated. Although the MeOH extract and pregnane glycosides (at different doses) were found to promote platelet aggregation, flavinantine (3) and O-methylflavinantine (4) showed only slight activity. The ability of the MeOH extract and the four compounds to act synergistically with thrombin was also evaluated. All the tested compounds were successful in augmenting the aggregating effect of thrombin, although to different degrees.
Assuntos
Plantas Medicinais/química , Agregação Plaquetária/efeitos dos fármacos , Pregnanos/farmacologia , Plaquetas/efeitos dos fármacos , Plaquetas/enzimologia , Brasil , Sequência de Carboidratos , Sobrevivência Celular/efeitos dos fármacos , Glicosídeos/química , Glicosídeos/farmacologia , Humanos , Técnicas In Vitro , L-Lactato Desidrogenase/metabolismo , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Pregnanos/química , Espectrometria de Massas de Bombardeamento Rápido de ÁtomosRESUMO
Six new oleanene glycosides were isolated from the MeOH extract of the aerial parts of Spergularia ramosa. They possess gypsogenin or quillaic acid as the aglycons. The disaccharide moiety linked to C-3 of the aglycons is made up of galactose (or glucose) and glucuronic acid (or glucose); the pentasaccharide moiety linked to C-28 is made up of glucose (or galactose), xylose, rhamnose, fucose, and arabinose. Their structures were elucidated by 1D and 2D NMR experiments including 1H-1H (DQF-COSY, 1D TOCSY, 2D HOHAHA, ROESY) and 1H-13C (HSQC, HMBC) spectroscopy.
Assuntos
Ácido Oleanólico/análogos & derivados , Plantas Medicinais/química , Saponinas/farmacologia , Triterpenos/farmacologia , Sequência de Carboidratos , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Peru , Extratos Vegetais/químicaRESUMO
The present study examined the effect of the MeOH extract, partially purified fraction (IV), and pure compounds from Argemone mexicana L. (Papaveraceae) on the morphine withdrawal in guinea pig isolated ileum. The MeOH extract, the partially purified fraction (IV), and the pure compounds isolated from A. mexicana significantly and in a concentration-dependent manner reduced the morphine withdrawal. Since the pure compounds were identified as protopine and allocryptopine, the observed effects could be related to these compounds. The results of the present study suggest that isoquinoline alkaloids may be potential agents in the treatment of drug abuse.