Estudo fitoquímico dos extratos de folhas, galhos e cascas do caule de Calycophyllum spruceanum Benth para testes de potencial de cosmético funcional
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Data
2016-02-18
Autores
Magrini, Viviane [UNESP]
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Editor
Universidade Estadual Paulista (Unesp)
Resumo
O gênero Calycophyllum pertence à família Rubiaceae, conhecida pela diversidade de metabólitos secundários, e pela variedade de atividades biológicas: antifúngica, bactericida, antiviral e inseticida. A espécie vegetal Calycophyllum spruceanum Benth (Rubiaceae) é muito utilizada pelas populações da América do Sul no combate a doenças dermatológicas, estomacais, diabetes, parasitoses, câncer, entre outras, despertando o interesse pela investigação química deste táxon. A presente pesquisa objetivou o estudo bio-guiado dos extratos obtidos das folhas, galhos e de cascas do caule de C. spruceanum visando à identificação das substâncias bioativas isoladas, incluindo as inativas. A meta é identificar nas substâncias isoladas aquelas com propriedades cosméticas associadas ao uso popular desta espécie, conhecida na região Amazônica por esta propriedade. Diferentes extratos foram preparados e analisados por Cromatografia Líquida de Alta Eficiência (CLAE) e Espectroscopia de Ressonância Magnética Nuclear (RMN 1H), acompanhados por ensaios biológicos (ensaio de capacidade redutora dos radicais DPPH˙ e ABTS˙+) para determinação de atividade antioxidante. O direcionamento do estudo foi feito em função dos ensaios antioxidantes aplicados aos extratos, conduzindo o estudo experimental para o extrato hidroetanólico de folhas ao foco do estudo, por ter apresentado a maior atividade antioxidante. Por meio de métodos espectroscópicos e espectrométricos (CLAE-DAD, CLAE-EM, CLAE-EM/EM; RMN de 1H e 13C; TOCSY 1D; HMBC; EM-IES) deste extrato e respectivas frações, pode-se identificar algumas substâncias antioxidantes potencialmente ativas, sendo estas: ácido 3,5-di-O-E-cafeoilquínico; duas séries homólogas de proantocianidinas (tipo-B) com grau de polimerização de 1 a 4, e proantocianidinas monoglicosiladas (tipo-B O-glicosilada) com grau de polimerização de 1 a 3; ácido 1,4-di-O-E-cafeoilquínico, quercetina 3-O-α-arabinopiranosil (16) β-glucopiranosídeo, ácido cafeoilquínico e canferol 3-O-β-D-glicopiranosil (12) β-D-xilopiranosídeo. Espera-se que ao final deste estudo, as informações forneçam subsídios para uma possível aplicação dos resultados científicos sobre a espécie vegetal, visando um produto para a linha de cosmético funcional.
The Calycophyllum genus belongs to the Rubiaceae’s family, known for its high diversity of secondary metabolites, which have a wide range of biological activities (antifungal, antibacterial, antiviral and pesticide). It is widely used by the people of South America against skin diseases, stomach, diabetes, parasites, cancer, among others. It is therefore essential to study the chemical composition of these species used in folk medicine, aiming to validate the traditional use, with scientific data and thus contributing to the search for new bioproducts. This research aimed the bio-guided fractionation of the extracts from the leaves, branches and stem bark extracts of Calycophyllum spruceanum Benth (Rubiaceae), to identify the secondary metabolites in the extracts and fractions, including bioactive ones, for further evaluation of the cosmetic potential of this species, commonly known in the Amazon region. Different extracts were prepared and analyzed by High Performance Liquid Chromatography (HPLC) and Nuclear Magnetic Resonance spectroscopy (1H NMR), and screened by biological assays (assay of reducing capability of ABTS˙+ and DPPH˙radicals) to determine the antioxidant activity. The chemical investigation was carried out based on the antioxidant activity of the extracts. The experimental study focused on the hydroethanolic extract of leaves, that presented the higher antioxidant activity, which would support the traditional uses of this specie as cosmetic. By means spectroscopic and spectrometric analysis (HPLC-DAD, HPLC-MS, HPLC-MS/MS; 1H NMR and 13C; TOCSY 1D; HMBC, ESI-MS) of this extract and its fractions, some compounds were identified: the 3,5-di-O-E-caffeoylquinic acid; two homologous series of proanthocyanidins (B-type) with a degree of polymerization from 1 to 4 and monoglicosyl proanthocyanidins (B-type O-glycosylated) with degree of polymerization from 1 to 3; 1,4-di-O-E-caffeoylquinic acid, quercetin-3-O-α-arabinopyranosyl (16) β-glucopyranoside, caffeoylquinic acid and kaempferol 3-O-β-D-glucopyranosyl (12) β-D-xilopyranosil, which could be responsible for the activity. It is expected that the the complete study of this species provide chemical information, which will validate this plant specie as a potential source of antioxidant natural products that could be material for functional cosmetics.
The Calycophyllum genus belongs to the Rubiaceae’s family, known for its high diversity of secondary metabolites, which have a wide range of biological activities (antifungal, antibacterial, antiviral and pesticide). It is widely used by the people of South America against skin diseases, stomach, diabetes, parasites, cancer, among others. It is therefore essential to study the chemical composition of these species used in folk medicine, aiming to validate the traditional use, with scientific data and thus contributing to the search for new bioproducts. This research aimed the bio-guided fractionation of the extracts from the leaves, branches and stem bark extracts of Calycophyllum spruceanum Benth (Rubiaceae), to identify the secondary metabolites in the extracts and fractions, including bioactive ones, for further evaluation of the cosmetic potential of this species, commonly known in the Amazon region. Different extracts were prepared and analyzed by High Performance Liquid Chromatography (HPLC) and Nuclear Magnetic Resonance spectroscopy (1H NMR), and screened by biological assays (assay of reducing capability of ABTS˙+ and DPPH˙radicals) to determine the antioxidant activity. The chemical investigation was carried out based on the antioxidant activity of the extracts. The experimental study focused on the hydroethanolic extract of leaves, that presented the higher antioxidant activity, which would support the traditional uses of this specie as cosmetic. By means spectroscopic and spectrometric analysis (HPLC-DAD, HPLC-MS, HPLC-MS/MS; 1H NMR and 13C; TOCSY 1D; HMBC, ESI-MS) of this extract and its fractions, some compounds were identified: the 3,5-di-O-E-caffeoylquinic acid; two homologous series of proanthocyanidins (B-type) with a degree of polymerization from 1 to 4 and monoglicosyl proanthocyanidins (B-type O-glycosylated) with degree of polymerization from 1 to 3; 1,4-di-O-E-caffeoylquinic acid, quercetin-3-O-α-arabinopyranosyl (16) β-glucopyranoside, caffeoylquinic acid and kaempferol 3-O-β-D-glucopyranosyl (12) β-D-xilopyranosil, which could be responsible for the activity. It is expected that the the complete study of this species provide chemical information, which will validate this plant specie as a potential source of antioxidant natural products that could be material for functional cosmetics.
Descrição
Palavras-chave
Calycophyllum spruceanum, Rubiaceae, CLAE, EM-IES, RMN, Fenólicos, Antioxidantes, HPLC, ESI-MS, NMR, Phenolics, Antioxidants