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Estudo da atividade antibacteriana da Carvona e seus derivados

Authors: Pinto, Patrícia Raquel Nascimento;

Estudo da atividade antibacteriana da Carvona e seus derivados

Abstract

Os conhecimentos acerca das plantas medicinais e da sua utilização, têm vindo a desenvolver-se de forma gradual desde a antiguidade até aos nossos dias. Os óleos essenciais são designados como misturas naturais e complexas de substâncias voláteis, responsáveis pela fragância de muitas espécies devido ao odor forte que os caracteriza. Apresentam baixa solubilidade em água e têm uma aparência oleosa à temperatura ambiente. Os óleos essenciais são formados em plantas aromáticas, obtidos nas folhas, flores, frutos, sementes, raízes ou caules das plantas como metabolitos secundários. Na sua constituição podem apresentar maioritariamente monoterpenos e sesquiterpenos. Podem conter cerca de 20 a 60 componentes em concentrações bastante diferentes e são caracterizados por dois ou três componentes maioritários em concentrações bastante elevadas (20-70%). Normalmente, os componentes maioritários determinam as propriedades biológicas dos óleos essenciais. A carvona é um exemplo de óleo essencial. É uma cetona pertencente ao grupo dos monoterpenos com propriedades odoríferas, sendo os seus derivados largamente empregues na indústria farmacêutica e alimentar. Estudos com plantas e óleos essenciais contendo este monoterpeno na sua constituição, têm demonstrado efeitos no sistema nervoso central, anticonvulsionante, atividade antibacteriana e atividade citotóxica para células cancerígenas. É encontrada na Natureza na forma de dois isómeros: (+)-carvona e a (-)-carvona. A (-)-carvona é extraída da hortelã ( Mentha spicata), sendo o seu maior constituinte. Já a (+)-carvona é o maior constituinte de Carum carvi L. Atualmente, existem diversos métodos de screening para definir se o extrato de uma determinada planta possui atividade antimicrobiana. Os dois métodos mais utilizados são os de difusão em agar e de diluição em caldo. Este trabalho consistiu em realizar reações de oxidação de cetonas com o catalisador HT de MgAl com uma mistura de H2O2 (30%)/Benzonitrilo a partir da R-(-)-carvona ou p-mentha-6,8-dien-2-one(-)-carvone, para obtenção dos principais produtos de oxidação e epoxidação, 7,8-epoxicarvona e 1,6,7,8-diepoxicarvona, para posterior estudo de atividade antibacteriana. Utilizou-se o método de difusão em agar com cavidades cilíndricas (poços) para a determinação dos halos de inibição, o método de macrodiluição para a determinação da concentração mínima inibitória (CMI) e da concentração mínima bactericida (CMB) e o teste em placa para a determinação do efeito de vapor. As estirpes estudadas foram: Escherichia coli, Pseudomonas aeruginosa e Staphylococcus aureus. De acordo com os resultados obtidos, o óleo essencial em bruto e suas diluições tem efeitos antibacterianos fortes sobre bactérias Gram-positivas e mais fracos sobre as bactérias Gram-negativas. Já a R-(-)-carvona e os seus derivados não apresentaram qualquer atividade na concentração de 0,5 mg/mL. Posteriormente efetuaram-se ainda o método de difusão em agar pela técnica de poço e o método dos vapores para a sulfona 7 e 8 (compostos de síntese orgânica quimioterápicos).

The knowledge about medicinal plants and their use, have been develop gradually from antiquity to the present day. Essential oils are classified as natural and complex mixtures of volatile substances responsible for the fragrance of many species, because of the strong odor which characterizes them. Have low solubility in water and have an oily appearance at room temperature. Essential oils are composed of aromatic plants, obtained from the leaves, flowers, fruits, seeds, roots or stems of the plant as secondary metabolites. In its present constitution can mostly monoterpenes and sesquiterpenes. May contain about 20 to 60 parts in very different concentrations they are characterized by two or three majority at very high concentrations (20-70%) components. Typically, the major components determine the biological properties of essential oils. This is an example of carvone essential oil. It belongs to a ketone group with odor properties of monoterpenes, and their derivatives widely employed in pharmaceutical and food industry. Studies in plants and this monoterpene containing essential oil in its composition, have demonstrated effects on the central nervous system anticonvulsant, antibacterial activity and cytotoxic activity to cancer cells. It is found in nature in the form of two isomers: (+)-carvone and (-)-carvone. The (-)-carvone is extracted from peppermint (Mentha spicata), and its major constituent. Since the (+)-carvone is the major constituent of Carum carvi L. Currently, there are several screening methods to determine whether the extract of a particular plant has antimicrobial activity. The two most common methods are the agar diffusion and broth dilution. This work was to carry out the oxidation of ketones with MgAl HT catalyst with a mixture of H2O2 (30%)/Benzonitrile from R-(-)- carvone or p-mentha-6,8-dien-2-one(-)-carvone, to obtain the main products of oxidation and epoxidation, 7,8-epoxicarvone and 1,6,7,8-diepoxicarvone for further study of antibacterial activity. We used the method of diffusion in agar with cylindrical cavities (wells) to determine the inhibition zones, the macrodilution method for determining the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (CMB) and the assay plate for determining the effect of steam. The strains studied were: Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus. According to the results, the bulk crude oil and dilutions thereof has strong antimicrobial effects on Gram-positive bacteria and weaker on the Gram-negative bacteria. Already the R (-)-carvone and its derivatives showed no activity at 0.5 mg/mL. Subsequently effected even the method by agar diffusion technique well and the method of vapor to the sulfone 7 and 8 (chemotherapeutic compounds organic synthesis).

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Carvona, Óleo Essencial, Domínio/Área Científica::Engenharia e Tecnologia::Engenharia Química, Concentração Mínima Bactericida, Concentração Mínima Inibitória, Atividade Antibacteriana, Sulfona

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selected citations
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This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
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popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
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influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
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impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
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