RESUMO
Cucurbitacins are triterpene bioactive constituents of natural products, particularly in the Cucurbitaceae plant family. The presence of cucurbitacins in seeds of the Cucurbita genus (pumpkin) has been only little studied. In this work, the content of cucurbitacins B, D, and E in seed oils from three cucurbits (Cucurbita moschata Duch, Cucurbita pepo Linn, and Cucurbita maxima Linn) was studied. An analytical method based on HPLC-DAD for the detection and quantification of these three cucurbitacins in seed oils was developed and validated according to ICH guidelines. The method showed good linearity, accuracy, and precision for the simultaneous quantification of cucurbitacins B, D, and E using C.moschata seed oil as a reference. When applied to C.pepo and C.maxima seed oils, cucurbitacin B and D were quantified but to a lesser extent. This is the first report of a simple, repeatable, and reproducible analytical tool to identify cucurbitacins in oilseeds from Cucurbita spp.
RESUMO
Cucurbitacins are a wide group of natural products found in several plant families, especially in the Cucurbitaceae family. In the last decade, there has been a significant increase in studies aimed at identifying new biological activities of cucurbitacins and describing their mechanisms of action. The most researched pharmacological activities are antineoplastic and anti-inflammatory activity, the first being recently reviewed. The present review explains the anti-inflammatory, antioxidant, and immunomodulatory potential of cucurbitacins, identifying the most studied compounds in this area and exploring their mechanisms of action already studied. A brief report was made about the main structural characteristics of cucurbitacins, in addition to an update on the biological activities attributed to this class in the last 5 years. Cucurbitacin B and cucurbitacin E have been identified as the most investigated when it comes to the immune response, playing roles in both innate and adaptive immunity. The most cited mechanisms were inhibition of COX-2 and NOS, reduction of oxidative stress, suppression of proinflammatory cytokines and modulation of acquired immunity proteins. It was found that cucurbitacins are promising molecules in the search for therapeutic innovation and have wide versatility in the immune response.
Assuntos
Cucurbitacinas , Triterpenos , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/uso terapêutico , Antioxidantes/farmacologia , Antioxidantes/uso terapêutico , Cucurbitacinas/química , Cucurbitacinas/farmacologia , Cucurbitacinas/uso terapêutico , Humanos , Sistema Imunitário , Imunidade , Triterpenos/farmacologia , Triterpenos/uso terapêuticoRESUMO
Roots of Wilbrandia ebracteata Cogn., Cucurbitaceae, used in folk medicine for treatment of rheumatic disease, are rich in cucurbitacins. Dihydrocucurbitacin B is the most abundant cucurbitacin while cucurbitacin B is a minor component. A reverse-phase HPLC system was developed for simultaneous quantitative assay of these cucurbitacins in the roots. The optimised experimental conditions were acetonitrile/H(2)0 40:60, flow-rate 1.2 mL/min., detection at 230 nm and isocratic elution. A variety of sample preparation modes were tested and the extraction with dichloromethane under reflux gave better results. The validation process included linearity, accuracy, repeatability and intermediate precision. The calibration curve of dihydrocucurbitacin B was linear from 40.00 to 400 μg/mL, the recovery was 95.5±3.01 percent, the intermediate precision was found to be 1.64 percent and the repeatability varied between 1.30 to 2.05 percent. The calibration curve of cucurbitacin B was linear from 4.00 to 240 μg/mL, intermediate precision was found to be 2.29 percent and repeatability varied between 1.03 to 2.95 percent. Analysis of the same specimen of W. ebracteata every year from 2002 to 2005 revealed a great rise on the cucurbitacin B concentration after the root was attacked by an herbivore.
Raízes de Wilbrandia ebracteata Cogn. (Cucurbitaceae), tradicionalmente empregada no tratamento de doenças reumáticas, contém cucurbitacinas, sendo di-hidrocucurbitacina B a mais abundante, enquanto cucurbitacina B está presente em menor quantidade. Foi desenvolvido um método para determinação quantitativa destas cucurbitacinas. Os parâmetros selecionados foram: eluente isocrático acetonitrila/H(2)0 40:60, fluxo 1,2 mL/min. e detecção em 230 nm. Diversas formas de preparo da amostra foram testadas, sendo que extração com diclorometano sob refluxo forneceu o melhor resultado. O processo de validação incluiu: linearidade, exatidão, repetibilidade e precisão intermediária. A curva de calibração para a di-hidrocucurbitacina B foi linear de 40.00 to 400 μg/mL, a recuperação foi 95,5±3.01 por cento, a precisão intermediária, 1,64 por cento e a repetibilidade variou entre 1,30 a 2,05 por cento. A curva de calibração da cucurbitacina B foi linear de 4,00 to 240 μg/mL, a recuperação encontrada foi igual a 96,6±2.45 por cento, a precisão intermediária, 2,29 por cento e a repetibilidade variou entre 1,03 a 2,95 por cento. Análise do mesmo espécime de W. ebracteata uma vez por ano de 2002 a 2005 revelou grande aumento no teor de cucurbitacina B após a raiz ter sido atacada por herbívoro.