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Lucienir Pains Duartehttp://lattes.cnpq.br/8518098370099915Rossimiriam Pereira de FreitasRosemeire Brondi AlvesVanessa Gregório RodriguesRosilene Aparecida de Oliveirahttp://lattes.cnpq.br/2715023625551749Karen Caroline Camargo2022-09-08T21:26:53Z2022-09-08T21:26:53Z2022-05-20http://hdl.handle.net/1843/45020Plantas pertencentes à família Celastraceae são consideradas como fontes promissoras de compostos bioativos, destacando-se os triterpenos pentacíclicos (TPs). Neste contexto, este trabalho teve como objetivo realizar um levantamento bibliográfico dos triterpenos pentacíclicos isolados de plantas da família Celastraceae entre os anos 2001 e 2021, realizar um estudo fitoquímico das folhas de Pristimera celastroides e das folhas e raízes de Fraunhofera multiflora e obter e caracterizar quimicamente óleos essenciais de diferentes partes e espécies dessa família. Os resultados obtidos foram apresentados em três capítulos. No Capítulo 1 foi descrito o levantamento bibliográfico, sendo relatados 504 triterpenos pentacíclicos isolados de espécies de Celastraceae entre os anos 2001 e 2021. Esses foram classificados como friedelanos (103), quinonametídeos (22), aromáticos (29), dímeros (50), lupanos (89), oleananos (102), ursanos (88) e outros (21). No capítulo 2 foram discutidos os resultados dos estudos fitoquímicos das espécies P. celastroides e F. multiflora. Da espécie P. celastroides foram isolados e identificados uma mistura de hidrocarbonetos (PC-1) e de ácidos carboxílicos (PC-3 e PC-6), dois compostos esterificados pertencentes a classe dos cicloartanos [3β-aciloxi-9,19-ciclolanost-24-eno (PC-4) e 3β-aciloxi-9,19-ciclolanostan-24,21-diol (PC-10)], o β-sitosterol na sua forma esterificada (3β-aciloxi-sitosterol, PC-8) e livre (PC-9), o esqualeno (PC-2), o polímero guta-percha (PC-5) e a vitamina E (α-tocoferol, PC-7). Por sua vez, o estudo fitoquímico das folhas e raízes de F. multiflora resultou no isolamento de três misturas de hidrocarbonetos (FM-1a, FM-1b e FM-1c) e duas misturas constituídas por isômeros da classe dos ursanos e oleananos: olean-12-en-3β,11α-diol (FM-8) + ursan-12-en-3β,11α-diol (FM-9) e ursan-11,12(13)-dien-3β-ol (FM-15) + olean-11,12(13)-dien-3β-ol (FM-16). Foram isolados TPs da classe dos friedelanos (friedelina, FM-2, e friedelinol, FM-14), ursanos (α-amirina, FM-4, e ácido ursólico, FM-7), oleananos (olean-11,13(18)-dien-3β-ol, FM-6) e quinonametídeos (pristimerina, FM-13). Além desses, foram isolados também o polímero guta-percha (FM-3), dois esteroides (β-sitosterol, FM-5, e 3-O-β-D-(6-O-aciloxi-glicosil)-β-sitosterol, FM-11) e misturas compostas por alcaloides macrocíclicos derivados da espermidina (FM-12a, FM-12b e FM-12c). Por fim, no capítulo 3 foi descrito um estudo comparativo da composição química de óleos essenciais extraídos de espécies de Celastraceae. Foram obtidos 17 óleos essenciais a partir de diferentes partes de nove espécies de Celastraceae, nos quais foram identificados por CG-EM um total de 130 constituintes diferentes. Os compostos comuns na maioria dos óleos essenciais foram os isômeros cis e trans-óxido de linalol, nerilacetona, linalol, β-ionona, α-ionona, nerolidol, decanal e ácido dodecanoico. Por meio da análise de componentes principais (PCA) verificou-se um perfil de similaridade na composição química dos óleos essenciais das espécies vegetais estudadas. Foram avaliadas as atividades antimicrobiana e inibitória da enzima cetilcolinesterase, nas quais os óleos essenciais apresentaram baixa ou nenhuma inibição. Os dados relatados nos três capítulos destacam a abundância e a diversidade estrutural de TPs isolados de espécies de Celastraceae, bem como os resultados obtidos no estudo dos óleos essenciais podem ser utilizados como referência para a realização de estudos quimiotaxonômicos.lants belonging to the Celastraceae family are considered as promising sources of bioactive compounds, especially pentacyclic triterpenes (TPs). This work aimed to carry out a bibliographic survey of pentacyclic triterpenes isolated from Celastraceae plants between the years 2001 and 2021, a phytochemical study of the leaves of Pristimera celastroides and leaves and roots of Fraunhofera multiflora and to obtain and chemically characterize essential oils from different parts and species of this family. The results obtained were presented in three chapters. In Chapter 1, the bibliographic survey was described, and 504 pentacyclic triterpenes isolated from Celastraceae species were reported between 2001 and 2021. These were classified as friedelanes (103), quinonamethides (22), aromatics (29), dimers (50), lupanes (89), oleananes (102), ursanes (88) and others (21). In chapter 2, the results of phytochemical studies of the species P. celastroides (leaves) and F. multiflora (leaves and roots) were discussed. From the species P. celastroides, a mixture of hydrocarbons (PC-1) and carboxylic acids (PC-3 and PC-6), two esterified compounds belonging to the class of cycloarthanes [3β-acyloxy-9,19-cyclolanostan-24-ene (PC-4) and 3β-acyloxy-9,19-cyclolanostan-24,21-diol (PC-10)], β-sitosterol in its esterified form (3β-acyloxy-sitosterol, PC-8) and free form (PC-9), squalene (PC-2), gutta-percha polymer (PC-5) and vitamin E (α-tocopherol, PC-7). The phytochemical study of F. multiflora resulted in the isolation of three mixtures of hydrocarbons (FM-1a, FM-1b and FM-1c) and two mixtures composed of isomers of the class of ursanes and oleananes: olean-12-en-3,11α-diol (FM-8) + ursan-12-en-3β,11α-diol (FM-9) e ursan-11,12(13)-dien-3β-ol (FM-15) + olean-11,12(13)-dien-3β-ol (FM-16). TPs of the following types were isolated: friedelanes (friedelin, FM-2, and friedelinol, FM-14), ursanes (α-amyrin, FM-4, and ursolic acid, FM-7), oleananes (olean-11,13(18)-dien-3β-ol, FM-6) and quinonamethides (pristimerin, FM-13). In addition to these, the polymer gutta-percha (FM-3), two steroids (β sitosterol, FM-5, and 3-O-β-D-(6-O-acyloxy-glycosyl)-β-sitosterol, FM-11) and mixtures composed of macrocyclic alkaloids derived from spermidine (FM-12a, FM-12b and FM-12c) were isolated. Finally, in chapter 3, a comparative study of the chemical composition of essential oils extracted from species of Celastraceae was described. Seventeen essential oils were obtained from different parts of nine species of Celastraceae. A total of 130 different constituents were identified by GC-EM, among which the cis and trans-oxide isomers of linalool, nerylacetone, linalool, β-ionone, α-ionone, nerolidol, decanal and dodecanoic acid, detected in most essential oils. The principal component analysis showed a similarity profile in the chemical composition of the essential oils of the studied plant species. The antimicrobial and anticholinesterase activities were evaluated, in which the essential oils showed low or no inhibition. The data reported in the three chapters highlight the abundance and structural diversity of TPs isolated from Celastraceae species, as well as the results obtained in the study of essential oils can be used as a reference for carrying out chemotaxonomic studies.CNPq - Conselho Nacional de Desenvolvimento Científico e TecnológicoporUniversidade Federal de Minas GeraisPrograma de Pós-Graduação em QuímicaUFMGBrasilICX - DEPARTAMENTO DE QUÍMICAQuímica orgânicaCelastraceaeProdutos naturaisEssências e óleos essenciaisTerpeniosProdutos de ação antimicrobianaHidrocarbonetosÁcidos carboxílicosCromatografia de gásEspectrometria de massaRessonância magnética nuclearAnálise de componentes principaisCelastraceaeTriterpenosÓleos essenciaisTriterpenesEssential oilsFamília Celastraceae: caracterização química de óleos essenciais de nove espécies, compilado dos triterpenos pentacíclicos com foco nos dados de RMN de 13C, estudo fitoquímico das folhas de Pristimera celastroides e das folhas e raízes de Fraunhofera multiflorainfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFMGinstname:Universidade Federal de Minas Gerais (UFMG)instacron:UFMGORIGINALTese Karen C Camargo - versão final.pdfTese Karen C Camargo - versão final.pdfapplication/pdf11617799https://repositorio.ufmg.br/bitstream/1843/45020/1/Tese%20Karen%20C%20Camargo%20-%20vers%c3%a3o%20final.pdf1838f3141fffff9a852fdd31ac25cd85MD51LICENSElicense.txtlicense.txttext/plain; charset=utf-82118https://repositorio.ufmg.br/bitstream/1843/45020/2/license.txtcda590c95a0b51b4d15f60c9642ca272MD521843/450202022-09-08 18:26:53.975oai:repositorio.ufmg.br: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ório InstitucionalPUBhttps://repositorio.ufmg.br/oaiopendoar:2022-09-08T21:26:53Repositório Institucional da UFMG - Universidade Federal de Minas Gerais (UFMG)false
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