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Maria Amelia Diamantino BoaventuraJacqueline Aparecida TakahashiLaurent Frederic GilJoao Maximo de SiqueiraLucienir Pains DuarteDorila Pilo VelosoJociani Ascari2019-08-13T13:16:25Z2019-08-13T13:16:25Z2011-03-29http://hdl.handle.net/1843/SFSA-8GASDUO presente trabalho consta de duas partes. Na Parte 1 é descrito o estudo fitoquímico do mesocarpo e epicarpo externo do pequi (Caryocar brasiliense Camb.), sendo a primeira vez que esta parte da planta é estudada. Foram isoladas seis substâncias puras, sendo elas, galato de etila, -hidroximetilfurfural, ácido gálico, chiquimato de metila, galato de metila e quatro misturas, ß-D-frutopiranose e ß-D-frutofuranose, a- e ß-D-glicose, lupeol e ácido oléico, ß-sitosterol e estigmasterol, contaminados com o ácido oléico. Foram avaliadas as atividades citotóxica, antioxidante, alelopática e antimicrobiana sobre o extrato bruto, frações e substâncias puras. Na Parte 2 desta tese foram feitas transformações químicas e biotransformações (pela utilização do fungo B. cinerea) de isocariolanos. Foram isolados 11 produtos de transformação química, sendo eles, 5a-hidroxicariofila- 4(12),8(13)-dieno, (8R,9R)-8-metoxi-isocariolan-9-ol, isocariolan-9-ona,(1S,2S, 5R,8S)-1,4,4-trimetiltriciclo[6.2.1.02, 5]undecano-8-carbaldeído,(8R,9R)-isocariolano -8,9-diol, isocariolan-9a-ol, (1R,2S,5R,8S)-8-hidroximetil-1,4,4-trimetil triciclo[6.2.1.02,5]undecano, (8R,9R)-8-etoxi-isocariolan-9-ol, (8R,9R)-8-propoxiisocariolan- 9-ol, (8R,9R)-8-butoxi-isocariolan-9-ol, (8R,9R)-8-pentoxi-isocariolan-9- ol e 13 novos produtos de biotransformação, sendo eles, (4R,8R,9R)-8-metoxiisocariolan- 9,15-diol, (3S,8R,9R)-isocariolan-3,8,9-triol, (4R,8R,9R)-isocariolan- 8,9,15-triol, (6R,8S,9R)-isocariolan-6,8,9-triol, (2R,5S,8R,9R)-isocariolan-5,8,9- triol, (6S,8S,9R)-isocariolan-6,8,9-triol, (2S,4R,5R)-4-hidroximetil-1,4-dimetiltriciclo [6.3.1.02,5]dodecan-9-ona, (15R,9R)-isocariolan-9,15-diol, (3S,9R)-isocariolan-9,3- diol, (1S,2S,5R,6S,8S)-1-metil-4,4,8-trimetilentriciclo[6.2.1.02,5]undeca-6ß,12-diol, (1R,2S,5R,6S,8R,9S)-1-metil-4,4,8-trimetilentriciclo [6.2.1.02,5]undeca-6ß,9ß,12- triol,(1R,2S,4R,5R,6S,8S)-1-metil-4,4,8- trimetilentriciclo [6.2.1.02,5]undeca-6ß,15,12 -triol, (1S,2S,5R,8S)-1-metil-4,4,8-trimetilentriciclo[6.2.1.02,5]undeca-12,14,15-triol. Foram realizados testes de avaliação das atividades fungistática e alelopática sobre alguns dos derivados isocariolânicos isolados.This Thesis consists of two parts. In Part 1, the phytochemical study of mesocarpe and external epicarpe of pequi (Caryocar brasiliense Camb.) and their biological activity are described. This study led to the isolation of six pure compounds, ethyl gallate, 5-hydroxymethylfurfural, gallic acid, methyl shikimate, methyl gallate and four mixtures, -D-fructopiranose and -D-fructofuranose, - and -D-glucose, lupeol and oleic acid, -sitosterol and stigmasterol, contaminated with oleic acid. Biological assays for citotoxic, antioxidant, antimicrobial and allelopathicactivities were carried out for the crude extract, fractions and pure substances. In Part 2 of this thesis we describe chemical transformations and biotransformations (by using the fungus B. cinerea) of isocariolane compounds, resulting in 11 new products of chemical transformations, 5-hidroxycaryophylla-4(12),8(13)-diene, (8R,9R)-8-methoxyisocariolan-9-ol, isocaryolan-9-one,(1S,2S,5R,8S)-1,4,4-trimetyltriciclo[6.2.1.02,5] undecane-8-carbaldehyde, (8R,9R)- isocaryolan-8,9-diol, isocaryolan-9-ol, (1R,2S,5R,8S)-8-hydroxymethyl-1,4,4- trimethyltricicle[6.2.1.02,5]undecan, (8R,9R)-8-etoxyisocariolan -9-ol, (8R,9R)-8- propoxyisocariolan-9-ol, (8R,9R)-8-butoxyisocariolan-9-ol, (8R,9R)-8- pentoxyisocariolan-9-ol and 13 new biotransformation products, (4R,8R,9R)-8-metoxyisocariolan-9,15-diol, (3S,8R,9R)-isocaryolan-3,8,9-triol, (4R,8R,9R)- isocaryolan-8,9,15-triol, (6R,8S,9R)-isocaryolan-6,8,9-triol, (2R,5S, 8R,9R)- isocaryolan-5,8,9-triol, (6S,8S,9R)-isocaryolan-6,8,9-triol, (2S,4R,5R)-4- hydroxymethyl-1,4-dimethyltricycle[6.3.1.02,5]dodecan-9-one, (15R,9R)-isocaryolan-9,15-diol, (3S,9R)- isocaryolan-9,3-diol, (1S,2S,5R,6S,8S)-1-methyl- 4,4,8-trimethylentricycle[6.2.1.02,5]undeca-6,12-diol, (1R,2S,5R,6S,8R,9S)-1- methyl-4,4,8-trimethylentricycle[6.2.1.02,5]undeca-6,9,12-triol, (1R,2S,4R,5R,6S, 8S)-1-methyl-4,4,8-trimethylentricycle[6.2.1.02,5]undeca-6,15,12-triol, (1S,2S,5R,8S)-1-methyl-4,4,8-trimethylentricycle[6.2.1.02,5]undeca-12,14,15-triol .Bioassays to evaluate fungistatic and allelophatic activities of someisoariolanes isolated were carried out.Universidade Federal de Minas GeraisUFMGQuímica orgânicaCaquiCaryocarQuímicaBiotransformação (Metabolismo)BiotransformaçãoSínteseIsocariolanos e derivadosCaryocar brasilienseEstudo do epicarpo e do mesocarpo externo do fruto de Caryocar brasiliense Camb. (pequi): síntese e biotransformação de isocariolanos e derivados para avaliação da atividade biológicainfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisinfo:eu-repo/semantics/openAccessporreponame:Repositório Institucional da UFMGinstname:Universidade Federal de Minas Gerais (UFMG)instacron:UFMGORIGINALtese_de_jociani_ascari___29_03_2011.pdfapplication/pdf51195247https://repositorio.ufmg.br/bitstream/1843/SFSA-8GASDU/1/tese_de_jociani_ascari___29_03_2011.pdf898d7229410b3d6feb69d019e720e893MD51TEXTtese_de_jociani_ascari___29_03_2011.pdf.txttese_de_jociani_ascari___29_03_2011.pdf.txtExtracted texttext/plain590097https://repositorio.ufmg.br/bitstream/1843/SFSA-8GASDU/2/tese_de_jociani_ascari___29_03_2011.pdf.txtea77bd09f96b1e78c24df09f6aa562b0MD521843/SFSA-8GASDU2019-11-16 04:40:07.696oai:repositorio.ufmg.br:1843/SFSA-8GASDURepositório InstitucionalPUBhttps://repositorio.ufmg.br/oaiopendoar:2019-11-16T07:40:07Repositório Institucional da UFMG - Universidade Federal de Minas Gerais (UFMG)false
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