RESUMO
The new labdane [(3R*,4aR*,7S*,10aS*,10bR*)-3-ethenyl-3,4a,7,10a-tetramethyl-dodecahydro-1H-naphtho-[2,1-b]-pyran-7-yl]-methylbenzoate together with other 7 labdanes were isolated from the aerial parts of Buddleja marrubiifolia. Compound structures were elucidated by spectroscopic methods. Some compounds showed moderate to weak antimicrobial activity towards a panel of bacterial and fungal pathogens. In addition, trans-biformene (2) and ribenol acetate (8) showed to be highly cytotoxic with LC50 < 1 µg/mL, the other compounds showed moderate cytotoxic effect with a LC50 range of 6.008-15.26 µg/mL. For all isolated compounds, no inflammatory response was observed.
Assuntos
Buddleja , Diterpenos , Bactérias/efeitos dos fármacos , Buddleja/química , Diterpenos/farmacologia , Fungos/efeitos dos fármacos , Humanos , Extratos Vegetais/farmacologia , Células THP-1RESUMO
Chemical profiling of Buddleja globosa was performed by high-performance liquid chromatography coupled to electrospray ionization (HPLC-DAD-ESI-IT/MS) and quadrupole time-of-flight high-resolution mass spectrometry (HPLC-ESI-QTOF/MS). The identification of 17 main phenolic compounds in B. globosa leaf extracts was achieved. Along with caffeoyl glucoside isomers, caffeoylshikimic acid and several verbascoside derivatives (ß-hydroxyverbascoside and ß-hydroxyisoverbascoside) were identified. Among flavonoid compounds, the presence of 6-hydroxyluteolin-7-O-glucoside, quercetin-3-O-glucoside, luteolin 7-O-glucoside, apigenin 7-O-glucoside was confirmed. Campneoside I, forsythoside B, lipedoside A and forsythoside A were identified along with verbascoside, isoverbascoside, eukovoside and martynoside. The isolation of two bioactive phenolic compounds verbascoside and forsythoside B from Buddleja globosa (Buddlejaceae) was successfully achieved by centrifugal partition chromatography (CPC). Both compounds were obtained in one-step using optimized CPC methodology with the two-phase solvent system comprising ethyl acetate-n-butanol-ethanol-water (0.25:0.75:0.1:1, v/v). Additionally, eight Natural Deep Eutectic Solvents (NADESs) were tested for the extraction of polyphenols and compared with 80% methanol. The contents of verbascoside and luteolin 7-O-glucoside after extraction with 80% methanol were 26.165 and 3.206 mg/g, respectively. Among the NADESs tested in this study, proline- citric acid (1:1) and choline chloride-1, 2- propanediol (1:2) were the most promising solvents. With these NADES, extraction yields for verbascoside and luteolin 7-O-glucoside were 51.045 and 4.387 mg/g, respectively. Taken together, the results of this study confirm that CPC enabled the fast isolation of bioactive polyphenols from B. globosa. NADESs displayed higher extraction efficiency of phenolic and therefore could be used as an ecofriendly alternative to classic organic solvents.
Assuntos
Buddleja/química , Extratos Vegetais/química , Polifenóis/química , Centrifugação , Cromatografia , Extratos Vegetais/classificação , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Polifenóis/classificação , Polifenóis/isolamento & purificação , Solventes/químicaRESUMO
Arthritis is a chronic inflammatory disease which reduces the life quality of affected individuals. Therapeutic tools used for treating inflammatory pain are associated with several undesirable effects. Buddleja thyrsoides Lam., known as 'Barbasco' or 'Cambara', is mostly used in several disorders and possesses antirheumatic, anti-inflammatory, and analgesic properties. Here, we investigated the antinociceptive and anti-inflammatory effects of the B. thyrsoides crude extract applied orally and topically in acute pain models and an arthritic pain model induced by complete Freund's adjuvant (CFA) paw injection in male mice (25-30â g). The high-performance liquid chromatography (HPLC) of the B. thyrsoides extract crude revealed the presence of the lupeol, stigmasterol, and ß-sitosterol. The stability study of the B. thyrsoides gel did not show relevant changes at low temperatures. The oral treatment with the B. thrysoides extract prevented the capsaicin-induced spontaneous nociception and the acetic acid-induced abdominal writhing, but did not alter the thermal threshold in the tail immersion test. The B. thyrsoides antinociceptive effect was not reversed by naloxone in the capsaicin test. The B. thyrsoides oral or topical treatment reversed the CFA-induced mechanical allodynia and thermal hyperalgesia with maximum inhibition (Imax) of 69 ± 6 and 68 ± 5% as well as 78 ± 15 and 87 ± 12%, respectively. Moreover, the topical but not oral treatment inhibited the CFA-induced cell infiltration, but did not reduce the paw edema significantly. The oral treatment with B. thyrsoides did not cause adverse effects. These findings suggest that the oral or topical treatment with B. thyrsoides presents antinociceptive actions in an arthritic pain model without causing adverse effects.
Assuntos
Analgésicos não Narcóticos/uso terapêutico , Anti-Inflamatórios não Esteroides/uso terapêutico , Artrite Experimental/tratamento farmacológico , Buddleja/química , Extratos Vegetais/uso terapêutico , Folhas de Planta/química , Dor Aguda/tratamento farmacológico , Administração Cutânea , Administração Oral , Analgésicos não Narcóticos/administração & dosagem , Analgésicos não Narcóticos/efeitos adversos , Analgésicos não Narcóticos/química , Animais , Anti-Inflamatórios não Esteroides/administração & dosagem , Anti-Inflamatórios não Esteroides/efeitos adversos , Anti-Inflamatórios não Esteroides/química , Brasil , Buddleja/crescimento & desenvolvimento , Estabilidade de Medicamentos , Armazenamento de Medicamentos , Etnofarmacologia , Géis , Temperatura Alta/efeitos adversos , Masculino , Camundongos , Triterpenos Pentacíclicos/administração & dosagem , Triterpenos Pentacíclicos/efeitos adversos , Triterpenos Pentacíclicos/análise , Triterpenos Pentacíclicos/uso terapêutico , Extratos Vegetais/administração & dosagem , Extratos Vegetais/efeitos adversos , Extratos Vegetais/química , Folhas de Planta/crescimento & desenvolvimento , Sitosteroides/administração & dosagem , Sitosteroides/efeitos adversos , Sitosteroides/análise , Sitosteroides/uso terapêutico , Estigmasterol/administração & dosagem , Estigmasterol/efeitos adversos , Estigmasterol/análise , Estigmasterol/uso terapêutico , ViscosidadeRESUMO
The antioxidant and antihemolytic properties contained in the leaves of Buddleja globosa (B. globosa), also known as "Matico," were determined. Aqueous extracts of leaves were assayed in human erythrocytes and molecular models of its membrane. The latter were bilayers built-up of lipids located in the outer and inner leaflets of the erythrocyte membrane. Observations by scanning electron microscopy showed that the extract altered the morphology of erythrocytes inducing the formation of crenated echinocytes. This result implied that the extract components were inserted into the outer leaflet of the cell membrane. This conclusion was confirmed by experiments carried out by fluorescence spectroscopy of red cell membranes and vesicles (LUV) of dimyristoylphosphatidylcholine (DMPC) and by X-ray diffraction of DMPC and dimyristoylphosphatidylethanolamine bilayers. Human erythrocytes were in vitro exposed to HClO, which is a natural powerful oxidant. Results demonstrated that low concentrations of B. globosa aqueous extract neutralized the harmful capacity of HClO. Hemolysis experiments also showed that the extract in very low concentrations reduced hemolysis induced by HClO.
Assuntos
Antioxidantes/farmacologia , Buddleja/química , Membrana Eritrocítica/efeitos dos fármacos , Hemólise/efeitos dos fármacos , Extratos Vegetais/farmacologia , Antioxidantes/química , Cromatografia Líquida de Alta Pressão , Dimiristoilfosfatidilcolina/química , Eritrócitos/efeitos dos fármacos , Humanos , Microscopia Eletrônica de Varredura , Extratos Vegetais/química , Difração de Raios XRESUMO
Ultraviolet radiation (UVR) is involved in both sunburn and the development of skin cancer, which has a high incidence worldwide. Strategies to reduce these effects include the use of photoprotective substances. The aim of this work was to investigate the photoprotective effect of verbascoside isolated from the methanolic extract of Buddleja cordata (BCME) in SKH-1 mice exposed to acute and chronic UV-B radiation. The mouse dorsal area was evaluated macroscopically and microscopically for diagnosis; verbascoside penetration into mouse skin was investigated in vivo by the tape stripping method. After acute UV-B exposure, 100 percent of irradiated mice that had been protected with verbascoside showed no signs of sunburn or of inflammatory processes. After chronic exposure, 100 percent of unprotected mice showed skin carcinomas; in contrast, in mice topically treated with either BCME or verbascoside, the presence of lesions was decreased by 90 percent. These results prove that verbascoside penetrates through the skin of mice and suggest that verbascoside and BCME may potentially prevent photodamage on mices skin after acute and chronic UVR exposure.
La radiación ultravioleta (RUV) provoca quemaduras solares y el desarrollo de cáncer de piel. El objetivo de este trabajo fue investigar el efecto fotoprotector del verbascósido obtenido del extracto metanólico de Buddleja cordata (EMBC) en ratones SKH-1 expuestos a RUV-B de manera aguda y crónica. El diagnóstico histológico se llevó a cabo en la piel de la zona dorsal de los ratones. La penetración del verbascósido fue cuantificada mediante la técnica de la cinta adhesiva. En el experimento agudo, el 100 por ciento de los ratones protegidos con verbascósido no evidenciaron signos de quemadura ni procesos inflamatorios. En el experimento crónico los ratones sin protección e irradiados presentaron carcinomas cutáneos. En contraste en los ratones protegidos con EMBC o verbascósido las lesiones disminuyeron un 90 por ciento en ambos grupos. El verbascósido penetró en la piel del ratón. Los resultados sugieren que el EMBC y el verbascósido previenen el fotodaño en la piel de ratones expuestos de forma aguda o crónica a la RUV.
Assuntos
Animais , Camundongos , Buddleja/química , Fenóis/farmacologia , Extratos Vegetais/farmacologia , Pele , Pele/efeitos da radiação , Eritema/prevenção & controle , Glucosídeos/farmacologia , Camundongos Pelados , Pele/patologia , Queimadura Solar/prevenção & controle , Raios Ultravioleta/efeitos adversosRESUMO
The estrous cycle disruptor effect of an ethanolic extract (EMATst) from Buddleja globosa leaves and standardized in its main component (verbascoside) was determined in rats after the subcutaneous administration of EMATst. Binding of EMATst and verbascoside to the estrogen receptor (ER) of EMATst and verbacoside was also measuredestablished. EMATst produced a significant alteration inof the estrous cycle only at the highest dose (10-5 M), which could be attributed to an antiestrogenic effect. The Bbinding of EMATst and verbascoside to the ER was competitive and occurred in concentrations 1000 times greater than that of 17beta-estradiol.
El efecto disruptor del ciclo estral de un extracto etanólico (EMATst) obtenido a partir de las hojas de Buddleja globosa y estandarizado en su componente mayoritario (verbascósido) fue determinado en ratas después de la administración subcutánea de EMATst. Se estableció además la unión al receptor estrogénico (RE) tanto de EMATst como de verbascósido. EMATst sólo a la dosis más alta (10-5M) produjo una alteración significativa del ciclo estral, lo que podría atribuirse a un efecto antiestrogénico. La unión al RE de EMATst y verbascósido se produjo a concentraciones 1000 veces mayor que el 17beta-estradiol y de forma competitiva.
Assuntos
Animais , Ratos , Buddleja/química , Ciclo Estral , Extratos Vegetais/farmacologia , Fenóis/farmacologia , Glucosídeos/farmacologia , Etanol , Folhas de Planta/química , Ratos Sprague-Dawley , Receptores de EstrogênioRESUMO
This study is designed to examine the chemical composition of the essential oil obtained from Buddleja thyrsoides Lam leaves from south Brazil. Gas chromatography/mass spectrometry analysis resulted in the detection of 12 components, representing 91.4% of the total oil composition. Germacrene D (27.16%), 1,10-di-epi-Cubenol (13.37%), α-Cadinol (12.95%), Bicyclogermacrene (9.00%), Globulol (8.59%) and caryophylene E (5.26%) were the main components. To the best of our knowledge, this is the first study of the composition of essential oil of the B. thyrsoides collected in Brazil.
Assuntos
Buddleja/química , Óleos Voláteis/análise , Folhas de Planta/química , Óleos de Plantas/análise , Sesquiterpenos/isolamento & purificação , Brasil , Destilação , Cromatografia Gasosa-Espectrometria de Massas , Sesquiterpenos/químicaRESUMO
The phenylpropanoid glycoside verbascoside [2-(3,4-dihydroxyphenylethyl)-1-O-α-L-rhamnopyranosyl-(1â3)-ß-D-(4-O-caffeyl)-glucopyranoside] (1) has been isolated as the main constituent of the crude extract of Buddleja brasiliensis Jacq. ex Spreng from Southern Brazil. The crude extract, main fractions and the compound 1 were evaluated for inhibition of the enzymes acetylcholinesterase (AChE), dipeptidyl peptidase-IV (DPP-IV) and prolyl oligopeptidase (POP). Compound 1 showed weak activity against DPP-IV with an IC(50) >> 150 µM and was inactive against AChE, with a pMIQ determined by bioautography of 9.6. In contrast, 1 displayed significant inhibition of POP in a dose-dependent manner with an IC(50) value of 1.3 ± 0.2 µM, similar to the positive control, baicalin, with a POP IC(50) of 12 ± 3 µM.
Assuntos
Buddleja/química , Glucosídeos/química , Fenóis/química , Serina Endopeptidases/química , Inibidores de Serina Proteinase/química , Fracionamento Químico , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Inibidores da Dipeptidil Peptidase IV/química , Inibidores da Dipeptidil Peptidase IV/isolamento & purificação , Glucosídeos/isolamento & purificação , Concentração Inibidora 50 , Fenóis/isolamento & purificação , Extratos Vegetais/química , Prolil Oligopeptidases , Inibidores de Serina Proteinase/isolamento & purificaçãoRESUMO
Alzheimer's disease (AD) is a neurodegenerative disorder resulting in impaired memory and behaviour of remarkable socio-economic impact. A decrease in cholinergic activity is a key event in the biochemical of AD. Buddleja thyrsoides is a plant widely distributed in Southern parts of South America. In Brazilian traditional medicine, the infusion of its leaves and flowers is used for the treatment of bronchitis and cough. Crude ethanolic (70%) extract and fractions (dichloromethane, ethyl acetate and n-butanolic) were investigated regarding their toxicities in vitro and antiplatelet action. The enzyme acetylcholinesterase inhibition was evaluated to study the crude extract. The crude extract and fractions were evaluated by means of Brine Shrimp Lethality test and they showed low activities with LC(50) values 1698, 2818, 2187 and 3672 µg mL(-1) for dichloromethane, ethyl acetate, n-butanolic fractions and crude extract, respectively. Buddleja thyrsoides presented great antiplatelet action. The IC(50) values obtained for crude extract and dichloromethane, ethyl acetate and n-butanolic fractions were 361.29, 354.23, 368.75 and 344.30, respectively, while the IC(50) for the standard AAS was 257.01 µg mL(-1). The crude extract showed an inhibition of 22.8% of the acetylcholinesterase enzyme in 24 h.
Assuntos
Buddleja/química , Inibidores da Colinesterase/farmacologia , Extratos Vegetais/farmacologia , Folhas de Planta/química , Inibidores da Agregação Plaquetária/farmacologia , Animais , Artemia/efeitos dos fármacos , Brasil , Inibidores da Colinesterase/toxicidade , Avaliação Pré-Clínica de Medicamentos/métodos , Dose Letal Mediana , Extratos Vegetais/toxicidade , Folhas de Planta/toxicidade , Plantas Medicinais/química , Inibidores da Agregação Plaquetária/toxicidadeRESUMO
Buddleja globosa Hope (matico) is a medicinal shrub native to Chile whose leaves have been traditionally used for wound and ulcer healing, pathologies associated to oxidative stress. Matico leaves display a high content of polyphenols, compounds with recognized antioxidant capacity, which may contribute to its therapeutic properties. Several factors, however, can modify the polyphenol content of matico leaf extracts, including plant material, production techniques, provenances, leaf age, harvest time, irrigation, and desiccation procedures. Thus, standardized leaf extracts prepared with plants from different provenances and harvest conditions were compared in terms of polyphenol content and their protecting antioxidant effects on rat liver microsomal lipids and thiol groups. All factors tested, but irrigation, changed both polyphenol content and antioxidant properties of matico extracts; water stress only affected their antioxidant properties without changing their polyphenol content. Correlation between polyphenol content and lipid peroxidation inhibition was only significant in the provenance study.
Buddleja globosa Hope (matico) es un arbusto medicinal nativo de Chile cuyas hojas han sido utilizadas en la medicina tradicional como cicatrizante en caso de patologías relacionadas con el estrés oxidativo. Las hojas tienen un alto contenido de polifenoles, compuestos con reconocidos efectos antioxidantes relacionados con la inhibición de la lipoperoxidación. Varios factores pueden afectar a su contenido, entre ellos el origen de la planta, edad de la hoja, momento de cosecha, riego y métodos de secado. En extractos estandarizados preparados de hojas de diferentes tratamientos se compararon el contenido de polifenoles y los efectos antioxidantes protectores de lipidos y grupos tioles microsomales. Todos los ensayos de cultivo y postcosecha mostraron diferencias significativas entre los tratamientos, excepto para la inhibición de lipoperoxidación en el tratamiento de riego. Plantas de diferente origen muestran que el contenido de polifenoles en las hojas es determinado genéticamente y sufre variaciones por efectos ambientales.