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Master's Dissertation
DOI
https://doi.org/10.11606/D.11.2008.tde-18112008-111056
Document
Author
Full name
Ingridy Simone Ribeiro Cabral
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
Piracicaba, 2008
Supervisor
Committee
Alencar, Severino Matias de (President)
Brazaca, Solange Guidolin Canniatti
Ikegaki, Masaharu
Title in Portuguese
Isolamento e identificação de compostos com atividade antibacteriana da própolis vermelha brasileira
Keywords in Portuguese
Abelhas
Agentes antimicrobianos-Isolamento e purificação
Cromatografia líquida de alta eficiência
Própolis.
Abstract in Portuguese
A própolis é uma substância resinosa coletada pelas abelhas de diversas partes das plantas, à qual têm sido atribuídas propriedades antimicrobiana, antioxidante, antinflamatória, antiviral, entre outras. Sua composição química depende de vários fatores, como a localização geográfica. Um novo tipo de própolis brasileira, denominada de própolis vermelha, por sua coloração intensa característica, foi identificada e coletada em região de mangue do Estado de Alagoas. O objetivo deste trabalho foi fracionar e isolar compostos com atividade antibacteriana dessa nova variedade de própolis. O extrato etanólico da própolis vermelha foi fracionado pela técnica de extração líquido-líquido, originando as frações hexânica (fr-Hex) e clorofórmica (fr-Clo). A fr-Clo apresentou alta atividade antibacteriana pelos testes de Concentração Inibitória Mínima (CIM) e Concentração Bactericida Mínima (CBM), contra as bactérias Staphylococcus aureus, Streptococcus mutans e Actinomyces naeslundii. Dessa forma, a fr-Clo foi refracionada por coluna seca gerando sete sub-frações. Após a avaliação da atividade antibacteriana das sub-frações pelas técnicas de CIM e CBM, a sub-fração 3, a mais bioativa, foi purificada em coluna de Sephadex LH-20. Dessa purificação foram obtidas três sub-frações bioativas, as quais foram submetidas ao isolamento dos compostos pela técnica de Cromatografia Líquida de Alta Eficiência (CLAE) preparativa. Dois compostos foram isolados e denominados de composto 1 e composto 2. O composto 2 foi o mais potente para as atividades inibitória e bactericida e sua CIM para os três tipos de bactéria testados variou entre 15,6 e 31,2 µg/mL, enquanto para o composto 1, este parâmetro variou de 31,2 a 62,5 µg/mL. As CBM do composto 1 e do composto 2 variaram entre 125 e 250 µg/mL e entre 31,2 e 62,5 µg/mL, respectivamente. Por meio da técnica Ressonância Magnética Nuclear (RMN) foi possível identificar o composto 1 como pertencente à classe das isoflavanas e o composto 2 como uma chalcona (isoliquiritigenina). A forte atividade antibacteriana apresentada pelos compostos isolados da própolis vermelha torna este produto uma importante fonte de compostos antibacterianos naturais.
Title in English
Isolation and identification of compounds presenting antibacterial activity in Brazilian red propolis
Keywords in English
Antimicrobial agents isolation and purification
Bees
High Performance Liquid Chromatography
Propolis.
Abstract in English
Propolis is a resinous material, collected by honeybees from several parts of plants, known for its antimicrobial, antioxidant, anti-inflammatory, antiviral properties, among others. Its composition varies according to several factors, such as the geographical location. A novel type of Brazilian propolis, named red propolis due to its intense characteristic color, was collected in a mangrove area in the State of Alagoas. This research aimed to fractionate and isolate the compounds in this new type of propolis that present antibacterial activity. The ethanolic extract of red propolis (EEP) was fractionated using the liquid-liquid extraction technique, yielding the hexanic (Hex-fr) and the chloroformic fractions (Chlo-fr). Chlo-fr showed high antibacterial activity determined by the minimal inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) tests against Staphylococcus aureus Streptococcus mutans, and Actinomyces naeslundii. Thus, Chlo-fr was refractionated by Dry-Column Chromatography, yielding seven subfractions. After submitted to MIC and MBC techniques to assess their antibacterial activity, and subfraction 3, the most bioactive of them, was purified in Sephadex LH-20 column. After this purification, three bioactive subfractions were obtained, submitted to isolation of compounds using preparative High Performance Liquid Chromatography (HPLC). Two compounds were isolated and named compound 1 and compound 2. Compound 2 presented the highest inhibitory and bactericidal activities and its MIC for the three types of bacteria tested ranged from 15.6 to 31.2 µg/mL, whereas for compound 1, this parameter ranged from 31.2 to 62.5 µg/mL. MBC of compound 1 and compound 2 ranged from 125 to 250 µg/mL and from 31.2 to 62.5 µg/mL, respectively. Through Nuclear Magnetic Resonance tecnique (NMR), it was possible to identify the compound 1 as belonging to class of isoflavans and the compound 2 as a chalcone (isoliquiritigenin). Due to the strong antibacterial activity presented by the compounds isolated from red propolis, it can be concluded that this product is an important source of natural antibacterial compounds.
 
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Ingridy_Cabral.pdf (4.00 Mbytes)
Publishing Date
2008-11-28
 
WARNING: The material described below relates to works resulting from this thesis or dissertation. The contents of these works are the author's responsibility.
  • ALENCAR, S.M., et al. Chemical composition and biological activity of a new type of Brazilian propolis: Red propolis. Journal of Ethnopharmacology, 2007, vol. 113, p. 278-283.
  • CABRAL, I.S.R., et al. Composição fenólica, atividade antibacteriana e antioxidante da própolis vermelha brasileira. Química Nova, 2009, vol. 32, p. 1523-1527.
  • OLDONI, T.L.C., et al. Isolation and analysis of bioactive isoflavonoids and chalcone from a new type of Brazilian propolis. Separation and Purification Technology, 2011, vol. 77, p. 208-2013.
  • CABRAL, Ingridy Simone Ribeiro, et al. Antibacterial activity of compounds isolated from a novel type of Brazilian propolis: red propolis. In 14th World Congress of Food Science & Technology, Shangai- China, 2008.
  • CABRAL, Ingridy Simone Ribeiro, et al. Atividade Antimicrobiana de frações e sub-frações de uma nova variedade de própolis brasileira. In 7º Simpósio Latino Americano de Ciência dos Alimentos, Campinas - SP, 2007.
  • CABRAL, Ingridy Simone Ribeiro, et al. Content of phenolic compounds and analysis of antimicrobial and antioxidant activity of a novel type of Brazilian propolis: red propolis. In 14th World Congress of Food Science & Technology, Shangai - China, 2008.
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