Isolamento de ?cidos terp?nicos de Jacaranda caroba, s?ntese e avalia??o da atividade antimicrobiana de derivados do ?cido urs?lico

• Author(s): Pereira, Nara R?bia
• Date: 2019
• Origin: Oasisbr
• Subject(s): Jacaranda caroba; ?cido urs?lico; ?cido 3-epicoros?lico; Ursolic acid; 3-epicorosolic acid
• Document Type: Master thesis
• Language: Portuguese

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Funda??o de Amparo ? Pesquisa do estado de Minas Gerais (FAPEMIG)

Alicer?ados na medicina popular, estudos envolvendo mol?culas oriundas de produtos naturais visam garantir qualidade, efic?cia e inova??o na formula??o de novos produtos, com a??o no tratamento e preven??o de doen?as. A flora brasileira possui uma vasta gama de esp?cies candidatas a pesquisas na inten??o de descoberta de novos f?rmacos. Um exemplo ? a Jacaranda caroba, que pode ser encontrada no cerrado, principalmente nos estados de SP, GO, MG e no DF. Em Minas Gerais, ? popularmente conhecida como ?carobinha?. As subst?ncias isoladas de esp?cies do g?nero Jacaranda mostraram a??es biol?gicas variadas: contra desordens g?stricas; doen?as de pele, hep?ticas, respirat?rias, inflamat?rias, microbianas e tumorais. O presente trabalho objetivou isolar ?cidos triterp?nicos, que apresentam potenciais atividades antimicrobianas, e sintetizar derivados do ?cido urs?lico, promissor produto com potencial biol?gico. Folhas de J. caroba foram submetidas ? extra??o com hexano, clorof?rmio e etanol, seus respectivos extratos foram submetidos a m?todos cromatogr?ficos cl?ssicos, sendo isolados e identificados os seguintes ?cidos: ?cido urs?lico e ?cido 3-epicoros?lico, sendo este in?dito na esp?cie. Neste trabalho foram sintetizados 8 ?steres a partir do triterpeno ?cido urs?lico, dentre eles dois s?o compostos in?ditos na literatura. Os compostos sintetizados e os fitoconstituintes foram submetidos a testes de a??o antibacteriana e antif?ngica. Os resultados obtidos de inibi??o antimicrobiana frente a diferentes cepas de bact?rias Gram-positivas e Gram-negativas e ao fungo leveduriforme Candida albicans, apresentaram-se promissores. Os melhores resultados no teste antimicrobiano foram encontrados para (3?)-3-[(naftalenobenzoil)oxi]urs-12-en-28-oico e para (3?)-3-[(2-iodobenzoil)oxi]urs-12-en-28-oico, ambos evidenciaram porcentagens de inibi??o de crescimento de 99,5% contra a bact?ria Gram-positiva Listenia Monocytogenes, superior ao padr?o Ampicilina (88,3%).

Disserta??o (Mestrado) ? Programa de P?s-Gradua??o em Qu?mica, Universidade Federal dos Vales do Jequitinhonha e Mucuri, 2018.

Based on popular medicine, studies involving molecules from natural products aim to guarantee quality, effectiveness and innovation in the formulation of new products, with action in the treatment and prevention of diseases. The Brazilian flora has a wide range of species that are candidates for research in the intention of discovering new drugs. An example is the Jacaranda caroba, which can be found in the cerrado, mainly in the states of SP, GO, MG and DF. In Minas Gerais, it is popularly known as "carobinha". Substances isolated from species of the genus Jacaranda showed varied biological actions: against gastric disorders; skin, liver, respiratory, inflammatory, microbial, and tumor diseases. The present work aimed to isolate triterpene acids, which present potential antimicrobial activities, and to synthesize the ursolic acid derivative, promising product with biological potential. Leaves of J. caroba were subjected to extraction with hexane, chloroform and ethanol, their extracts were submitted to classical chromatographic methods, being isolated and identified the following acids: ursolic acid and 3-epicorosolic acid, this being unheard of in the species. In this work 8 esters were synthesized from triterpene ursolic acid, among them two are compounds unpublished in the literature. The synthesized compounds and phytochemicals were submitted to antibacterial and antifungal tests. The results of antimicrobial inhibition against different strains of Gram-positive and Gram-negative bacteria and the yeast fungus Candida albicans, were promising. The best results in the antimicrobial test were found for Urs-12-en-28-oic acid [(naphthalenobenzoyl) oxy] (3?)-(3) and for Urs-12-en-28-oic acid [(2-iodobenzoyl)oxy] (3?)-(3), both showed percentages of 99,5% growth inhibition against Gram-positive Listenia Monocytogenes bacteria, higher than the Ampicillin standard (88.3%).