Thesis (M.S.)--University of Wisconsin, 1968. / eContent provider-neutral record in process. Description based on print version record.

Casearia membranacea Hance (Flacourtiaceae) is a tree found in the northern region of Taiwan. Bioassay-directed fractionation of the MeOH-layer has resulted in the isolation of six new clerodane diterpenes, Caseamembrins A-F (1-6) along with a known compound, rel-(2S,5R,6R, 8S,9S,10R,18S,19R)-diacetoxy-18,19-epoxy-6-hydroxy-2-(2-methylbut- anoyloxy)cleroda-3,13(16),14-triene (7). The structures of compounds 1-6 were determined by the physical methods such as IR¡Bmass¡Boptical rotation, 1D¡B2D NMR spectral analysis, and the published reports about the data of related compounds . The spectral data of 1-6 are in conformity with the basic skeleton of clerodane diterpenes previously isolated from Casearia membranacea Hance.. The basic structures of 1-6 contain two 6-membred ring linked with six carbon diene side chain at C-9 and two ester carbonyl functional groups at C-2 and C-18 respetirely. Compound 1 had an ester carbonyl at C-2 position, with an acetoxyl and a hydroxyl group at C-19/6 position, the structure of 1 was assigned as rel-(2S,5R,6R,8S,9S,10R,18S,19R)-18-butanoyloxy-19-acetoxy-18,19 -epoxy-6-hydroxy-2-(2-methylbutanoyloxy)cleroda-3,13(16),14-triene (Caseamembrin A). Compound 2 had a methoxyl group at C-18 position, that 2 has the structure of rel-(2S,5R,6R,8S,9S,10R,18S,19R)-18-methoxy -19-acetoxy-18,19-epoxy-6-hydroxy-2-(2-methylbutanoyloxy)cleroda-3,13(16),14-triene (Caseambrin B). Compound 3 had an acetoxyl at C-19 position, and two hydroxyl group at C-6/7. Compound 3 was assigned the structure of rel-(2S,5R,6R,7R,8S,9S,10R,18S,19R)-18-butanoyloxy-19- acetoxy-18,19-epoxy-6,7-dihydroxy-2-(2-methylbutanoyloxy)cleroda-3, 13(16),14- triene (Caseamembrin C). Compound 4 had two acetoxyl at C-7/19 and hydroxyl group at C-6, the assignment of its structure as rel-(2S,5R,6S,7R,8S,9S,10R,18S,19R)-18-butanoyloxy-19-acetoxy -18,19-epoxy-6-hydroxy-7-acetoxy-2-(2-methylbutanoyloxy)cleroda-3,13(16),14- triene (Caseamembrin D). Compound 5 had two acetoxyl at C-18/19 position, and a hydroxyl group at C-6 position. 5 was established as rel-(2S,5R,6R,8S,9S,10R,18S,19R)-18,19-diacetoxy-18,19-epoxy-6- hydroxy-2-(2-methylbutanoyloxy)cleroda-3,13(16),14-triene (Caseamembrin E). Compound 6 had a hydroxyl group at C-6 position and it was deduced that the C-18/19 acetal ring was opened thus forming the two aldehydic units. The structure of 6 was established as rel-(2S,5R,6R,7R,8S,9S,10R,18S,19R)-6-hydroxy-2-(2-methylbutanoyloy) cleroda-3,13(16),14-triene-18,19-dicarboxyaldehyde (Caseamembrin F). It is worthy to mention that this is the first report of the isolation of 1-6 from a natural source. In a preliminary pharmacological aporach (cytotoxicity), compounds 1-6 exhibited moderate cytotoxicity against (NUGC-3) and (HONE-1) cancer cells with IC50 0~1¢Mvalues at 20mg/ml.

Submitted by Marco Antônio de Ramos Chagas (mchagas@ufv.br) on 2017-06-08T17:32:10Z No. of bitstreams: 1 texto completo.pdf: 1118946 bytes, checksum: 7b5196d760d85c35a432644027f5d4b0 (MD5) / Made available in DSpace on 2017-06-08T17:32:10Z (GMT). No. of bitstreams: 1 texto completo.pdf: 1118946 bytes, checksum: 7b5196d760d85c35a432644027f5d4b0 (MD5) Previous issue date: 2016-03-21 / Coordenação de Aperfeiçoamento de Pessoal de Nível Superior / Em Casearia Jacq., glândulas estipulares são importantes para taxonomia, mas não são estrutural e funcionalmente descritas. Casearia destaca-se como um dos maiores gêneros de Salicaceae, suas espécies ocorrem em habitats diversos e algumas delas são medicinais. Os objetivos do presente trabalho foram esclarecer o tipo de glândula presente nas estípulas em Casearia, caracterizando-as anatomicamente, e verificar se ocorrem variações entre as glândulas de plantas provenientes do cerrado e da floresta. Foram selecionadas C. decandra Jacq., espécie típica de floresta, C. rufescens Cambess., que é endêmica do cerrado, e C. sylvestris Sw., que habita ambas as formações. Amostras de meristemas apicais e estípulas foram coletadas em campo ou obtidas em material herborizado, sendo processadas conforme metodologia usual para estudos anatômicos. As glândulas foram observadas no ápice, bordo e base das estípulas de C. decandra; no ápice e base de C. rufescens e C. sylvestris. São constituídas por um eixo central parenquimático multicelular avascularizado e por epiderme secretora uniestratificada em paliçada recoberta por cutícula fina, não sendo notadas diferenças anatômicas entre as espécies. Os testes histoquímicos detectaram polissacarídeos totais, pectinas/mucilagem e proteínas no citoplasma e na secreção acumulada no espaço subcuticular, bem como na que foi eliminada para o meio externo. Não foram notadas diferenças na natureza da secreção das glândulas estipulares conforme o ambiente de ocorrência da espécie, mas tais estruturas foram maiores nas espécies de floresta quando comparadas com as de cerrado. A estrutura anatômica, a atividade precoce e a natureza mucilaginosa da secreção permitem concluir que as glândulas estipulares das três espécies de Casearia são coléteres do tipo padrão, dado inédito para o gênero. Considerando a função atribuída aos coléteres de proteger os meristemas vegetativos e reprodutivos, os resultados obtidos são promissores, pois suscitam a investigação sobre a ocorrência e diversidade de coléteres estipulares no gênero Casearia, bem como a utilização taxonômica deste caráter. / In Casearia Jacq., stipular glands are important for taxonomy. However, these structures were not structurally and functionally described. Casearia stands out as one of the largest genera of Salicaceae, with species occurring in different habitats and some of them are used for medicinal purposes. The aims of the present study were clarify the gland types present in the stipules of three species of Casearia and verify the morphoanatomical variations between the glands of savanna and forest plants. The following species were selected: C. decandra Jacq., typical forest species, C. rufescens Cambess., which is endemic to the savanna, and C. sylvestris Sw., which occurs in both vegetation. Meristems samples and apical stipules were collected in the field or obtained from herbarium material. These samples were processed according to the standard methodology for anatomical studies. The glands were observed at the apex, margin and base of the stipules of C. decandra; only at the apex and base of both C. rufescens and C. sylvestris stipules. They consist of a non-vascular and multicellular parenchymal central axis, which is recovered by a one-single layer of secretory epidermis organized in a palisade with a thin cuticle. No anatomical differences among species were noticed. The histochemical tests detected total polysaccharides, pectins/mucilage and proteins in the cytoplasm, as well in the secretion accumulated in the subcuticular space and outside of epidermis. The histochemical results were the same for the secretion produced by stipule glands of species occurring in the different environment. However, the stipule glands of forest species are bigger than of the savanna species. The anatomical structure, early activity and mucilaginous nature of secretion allow concluding that the stipule glands of the three studied species of Casearia are standard type of colleters. This is the first register for the genus. Considering the role assigned to colleters to protect the vegetative and reproductive meristems, the results are promising since raise research on the occurrence and diversity of stipule colleters in Casearia, as well about the useful of this character for the taxonomic approaches.

Made available in DSpace on 2014-06-11T19:35:08Z (GMT). No. of bitstreams: 0 Previous issue date: 2010-03-10Bitstream added on 2014-06-13T19:45:03Z : No. of bitstreams: 1 vieirajunior_gm_dr_araiq.pdf: 24332689 bytes, checksum: 326a73ca2aa59e6829ca3ec7bf9a2b26 (MD5) / Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) / Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) / Este trabalho relata o estudo dos constituintes químicos de quatro espécies do gênero Casearia, bem como a avaliação das atividades antioxidante, anticolinesterásica, antifúngica e citotóxica de extratos e substâncias isoladas. O estudo da constituição química de C. gossypiosperma resultou no isolamento de três substâncias do extrato etanólico das folhas, sendo dois flavonóides: (+)-taxifolina (1) e quercetina (3) e um novo ciclitol: rel-(2R, 3S, 4R, 5R)-3,4,5-trihidroxi-2-etóxi- ciclohexanona (2). A partir do extrato hexânico das folhas de C. obliqua isolou-se quatro substâncias: o esteróide sitosterol (4) e três diterpenos clerodânicos: (rel)-2- benzoato-6-hidroxizuelanina + (rel)-6-benzoato-2-hidroxizuelanina (5+6) e 6- cinamato-2-hidroxizuelanina (7). Da fase etérea oriunda do extrato etanólico dos galhos foram isoladas cinco substâncias, sendo dois diterpenos clerodânicos inéditos: caseobliquina A (8) e caseobliquina B (9), um ácido fenólico simples: ácido cinâmico (10) e duas amidas: N-trans-p-cumaroiltiramina (11) e N-trans- feruloiltiramina (12). De C. rupestris foram isolados, a partir do extrato hexânico das folhas, quatro substâncias, sendo uma mistura de esteróide e diterpeno: sitosterol + E-fitol (4+13) e dois novos diterpenos clerodânicos, a casearupestrina B (16) e a casearupestrina D (18) e da fase hexânica do extrato EtOH das folhas foi isolado o diterpeno E-fitol (13). A partir da fase etérea também deste mesmo extrato foram isolados cinco diterpenos clerodânicos inéditos, as casearupestrinas A, B, C, D e G (14-18). A partir da casearupestrina A (14) e D (18) foram obtidos, por acetilação, mais dois diterpenos inéditos, as casearupestrinas E (14a) e F (18a), respectivamente. De C. decandra foi isolada a hidroquinona (19) a partir das fases hexânica, acetato de etila e hidroalcoólica, todas obtidas do extrato... / This work describes the study of the chemical constituents from four Casearia species, as well as the evaluation of antioxidant, anticholinesterasic, antifungal, and cytotoxic activities of extracts and the isolated chemical contituents. The study of the chemical constituents of C. gossypiosperma resulted in the isolation of three substances from ethanolic extract of the leaves, two flavonoids: (+)-taxifolin (1) and quercetin (3), and a new ciclitol: rel-(2R, 3S, 4R, 5R)-3,4,5-trihydroxy-2-ethoxy- cyclohexanone (2). From hexane extract of the leaves from C. obliqua were isolated four substances, the steroid sitosterol (4) and three clerodane diterpenes: (rel)-6- hydroxyzuelanin-2-benzoate + (rel)-2-hydroxyzuelanin-6-benzoate (5+6) and 2- hydroxyzuelanin-6-cinnamate (7). From ether phase obtained of the ethanolic extract from twigs of C. obliqua were isolated five substances, two new clerodane diterpenes: caseobliquin A (8) and caseobliquin B (9), one phenolic acid: cinnamic acid (10) and two amides: N-trans-p-coumaroyltyramine (11) and N-trans- feruloyltyramine (12). In C. rupestris four substances were isolated from hexane extract of leaves a mixture of a steroid and diterpene: sitosterol+E-phytol (4+13) and two new clerodane diterpenes: casearupestrin B (16) and casearupestrin D (18) and from hexane phase was isolated the diterpene E-phytol (13). Other five new clerodane diterpenes were isolated from ether phase obtained from ethanolic extract of leaves: casearupestrin A, B, C, D, and G (14-18). By acetylation, more two new clerodane diterpenes casearupestrin E (14a) and F (18a) were obtained from casearupestrin A (14) and D (18), respectively. From C. decandra was isolated the hidroquinon (19) of the hexane, ethyl acetate, and hydroalcoholic phases, every phases obtained from ethanolic extract of leaves. The structures of isolated compounds were determined by ... (Complete abstract click electronic access below)

O uso de plantas medicinais no tratamento de doenças tem aumentado de forma significativa nos últimos anos, bem como as pesquisas sobre a caracterização química destas plantas. Neste estudo, foram determinados os constituintes inorgânicos presentes nas folhas e nos extratos de três espécies da planta do gênero Casearia (C. sylvestris, C. decandra e C. obliqua) coletadas em regiões distintas da Mata Atlântica, SP. As composições elementares dos solos em que estas plantas foram cultivadas também foram determinadas. Tradicionalmente, estas plantas são utilizadas devido às suas propriedades antiinflamatórias, antiácidas, anti-sépticas e cicatrizantes. Além disso, as atividades antiulcerogênicas e antitumorais do gênero Casearia, e sua capacidade de neutralizar venenos de serpentes e abelhas, também tem sido comprovadas cientificamente. A metodologia analítica empregada foi a análise por ativação com nêutrons. Irradiações longas e curtas das amostras e dos padrões foram realizadas utilizando fluxos de nêutrons do reator de pesquisas IEA-R1 do IPEN/CNEN-SP. Nas folhas, o elemento K foi encontrado em níveis de porcentagens, os elementos Ca, Cl, Mg e Na na ordem de mg g-1, Br, Fe, Mn, Rb e Zn em μg g-1 e os elementos As, Co, Cr, Cs, La, Sb, Sc e Se em teores mais baixos, da ordem de ng g-1. Os resultados obtidos nas análises dos extratos indicaram que os mesmos elementos determinados nas folhas de Casearia foram também encontrados em seus respectivos extratos. A comparação das composições elementares das folhas de Casearia sylvestris coletadas em três regiões diferentes da Mata Atlântica mostrou que as concentrações dos elementos encontrados nas plantas dependem da composição dos solos em que elas foram cultivadas. Por outro lado, espécies diferentes do gênero Casearia cultivadas em uma mesma região apresentaram composições elementares similares. Estes resultados mostram a importância da realização de estudos que avaliem as atividades farmacológicas de Casearias cultivadas em diferentes tipos de solos. A qualidade analítica dos resultados foi avaliada pela análise dos materiais de referência certificados NIST 1573a Tomato Leaves, NIST 1515 Apple Leaves, INCT-TL-1 Tea Leaves, IAEA-Soil-7 e USGS W1. Os desvios padrão relativos e os erros relativos obtidos nestas análises indicaram boa precisão e exatidão dos resultados. / The use of medicinal plants in the treatment of diseases has increased significantly in the last years, as has research concerning chemical characterization of these plants. In this study, inorganic constituents were determined in leaves and in extracts from three medicinal plant species of the Casearia genus (C. sylvestris, C. decandra and C. obliqua) collected in distinct regions of the Atlantic Forest, SP. The elemental compositions of the soils in which these plants were grown were also determined. Traditionally, these plants are used due to their antiinflamatory, antiacid, antiseptic and cicatrizing properties. The antiulcer and the antitumor activities of the Casearia genus and its capacity to neutralize snake and bee venoms, have also been scientifically confirmed. The analytical methodology used was neutron activation analysis. Long and short irradiation periods of the samples and the standards were carried out at IPEN’s IEA-R1 nuclear research reactor. In the leaf K was found at the percentage levels, Ca, Cl, Mg and Na at mg g-1 levels and the elements Br, Fe, Mn, Rb and Zn at the μg g-1 levels. As, Co, Cr, Cs, La, Sb, Sc and Se at the ng g-1 levels. Results obtained in the extracts indicated that the same elements present in the leaves are also found in their extracts. The comparison between the inorganic composition of Casearia sylvestris leaves collected from three different regions of the Atlantic Forest showed that the elemental concentrations in the plants leaves varied depending on the place where they were grown. Different Casearia species cultivated in a same region presented similar elemental compositions. Based on these findings it can be concluded that the studies about the pharmacological effect of Casearia genus plants grown in different types of soil are of great importance. The quality of the obtained results was assured by the analyses of the certified reference materials NIST 1573a Tomato Leaves, NIST 1515 Apple Leaves, INCT-TL-1 Tea Leaves, IAEA-Soil-7 and USGS W1. The relative standard deviations and the relative errors obtained in these analyses indicated good precision and accuracy of the results.

O uso de plantas medicinais no tratamento de doenças tem aumentado de forma significativa nos últimos anos, bem como as pesquisas sobre a caracterização química destas plantas. Neste estudo, foram determinados os constituintes inorgânicos presentes nas folhas e nos extratos de três espécies da planta do gênero Casearia (C. sylvestris, C. decandra e C. obliqua) coletadas em regiões distintas da Mata Atlântica, SP. As composições elementares dos solos em que estas plantas foram cultivadas também foram determinadas. Tradicionalmente, estas plantas são utilizadas devido às suas propriedades antiinflamatórias, antiácidas, anti-sépticas e cicatrizantes. Além disso, as atividades antiulcerogênicas e antitumorais do gênero Casearia, e sua capacidade de neutralizar venenos de serpentes e abelhas, também tem sido comprovadas cientificamente. A metodologia analítica empregada foi a análise por ativação com nêutrons. Irradiações longas e curtas das amostras e dos padrões foram realizadas utilizando fluxos de nêutrons do reator de pesquisas IEA-R1 do IPEN/CNEN-SP. Nas folhas, o elemento K foi encontrado em níveis de porcentagens, os elementos Ca, Cl, Mg e Na na ordem de mg g-1, Br, Fe, Mn, Rb e Zn em μg g-1 e os elementos As, Co, Cr, Cs, La, Sb, Sc e Se em teores mais baixos, da ordem de ng g-1. Os resultados obtidos nas análises dos extratos indicaram que os mesmos elementos determinados nas folhas de Casearia foram também encontrados em seus respectivos extratos. A comparação das composições elementares das folhas de Casearia sylvestris coletadas em três regiões diferentes da Mata Atlântica mostrou que as concentrações dos elementos encontrados nas plantas dependem da composição dos solos em que elas foram cultivadas. Por outro lado, espécies diferentes do gênero Casearia cultivadas em uma mesma região apresentaram composições elementares similares. Estes resultados mostram a importância da realização de estudos que avaliem as atividades farmacológicas de Casearias cultivadas em diferentes tipos de solos. A qualidade analítica dos resultados foi avaliada pela análise dos materiais de referência certificados NIST 1573a Tomato Leaves, NIST 1515 Apple Leaves, INCT-TL-1 Tea Leaves, IAEA-Soil-7 e USGS W1. Os desvios padrão relativos e os erros relativos obtidos nestas análises indicaram boa precisão e exatidão dos resultados. / The use of medicinal plants in the treatment of diseases has increased significantly in the last years, as has research concerning chemical characterization of these plants. In this study, inorganic constituents were determined in leaves and in extracts from three medicinal plant species of the Casearia genus (C. sylvestris, C. decandra and C. obliqua) collected in distinct regions of the Atlantic Forest, SP. The elemental compositions of the soils in which these plants were grown were also determined. Traditionally, these plants are used due to their antiinflamatory, antiacid, antiseptic and cicatrizing properties. The antiulcer and the antitumor activities of the Casearia genus and its capacity to neutralize snake and bee venoms, have also been scientifically confirmed. The analytical methodology used was neutron activation analysis. Long and short irradiation periods of the samples and the standards were carried out at IPEN’s IEA-R1 nuclear research reactor. In the leaf K was found at the percentage levels, Ca, Cl, Mg and Na at mg g-1 levels and the elements Br, Fe, Mn, Rb and Zn at the μg g-1 levels. As, Co, Cr, Cs, La, Sb, Sc and Se at the ng g-1 levels. Results obtained in the extracts indicated that the same elements present in the leaves are also found in their extracts. The comparison between the inorganic composition of Casearia sylvestris leaves collected from three different regions of the Atlantic Forest showed that the elemental concentrations in the plants leaves varied depending on the place where they were grown. Different Casearia species cultivated in a same region presented similar elemental compositions. Based on these findings it can be concluded that the studies about the pharmacological effect of Casearia genus plants grown in different types of soil are of great importance. The quality of the obtained results was assured by the analyses of the certified reference materials NIST 1573a Tomato Leaves, NIST 1515 Apple Leaves, INCT-TL-1 Tea Leaves, IAEA-Soil-7 and USGS W1. The relative standard deviations and the relative errors obtained in these analyses indicated good precision and accuracy of the results.

ABSTRACT The Genus Casearia is a rich source of cleordane - type diterpenes. To search for practical sources of potential cleordane - type diterpenes, and to study the structure and activity relationship of cleordane - type diterpenes, the twigs and leaves of Casearia membranacea Hance ( Flacourtiaceae ) was collected for phytochemical and anti-tumor investigation. Bioassay-directed fractionation of an ethyl acetate layer of Casearia membranacea has resulted in the isolation of six new clerodane-type diterpenes. The structures of these cleordane-type diterpenes were established and designated as Caseamembrins G¡ãL¡]1¡ã6¡^and their derivatives compounds 7 and 8. The structures of compounds 1¡ã8 were determined by application of NMR techniques included 1H NMR, 13C NMR, DEPT, COSY, HMQC, HMBC, NOESY and another physical methods which include MS, UV, IR and optical rotation, and the published reports about the data of related compounds. The spectral data of 1¡ã8 are in conformity with the basic skeleton of cleordane-type diterpenes previously isolated from Casearia membranacea Hance. The basic structures of 1¡ã8 contain two 6- menbered ring. The structures were identified as rel-(2S,5R,6R,8S,9S,10R, 18S,19R)-2-hydroxy-6-butanoyloxy-18,19-acetyloxy-18,19-epoxy-cleroda-3,13(16),14-triene (Caseamembrin G, 1¡^¡Brel-(2S,5R,6R,8S,9S,10R,18S, 19R)-2-hydroxy-6,18-dibutanoyloxy-19-acetyloxy-18,19-epoxy-cleroda -3,13(16),14-triene (Caseamembrin H, 2¡^¡Brel-(2S,5R,6R,8S,9S,10R,18S ,19R)-2-(2-methylbutanoyloxy)-6-hydroxy-18-methoxy-19-acetyloxy-18,19-epoxy-cleroda-3,13(16),14-triene¡]Caseamembrin I, 3¡^¡Brel-(2R,5R ,6R,8S,9S,10R)-2-(2-methylbutanoyloxy)-6-hydroxy-cleroda-3,13(16),14 -triene-18,19-dicarboxaldehyde ( Caseamembrin J, 4¡^¡Brel-(2S,5R,6R,7R, 8S,9S,10R)-2,7-diacetyloxy-6-hydroxy-cleroda-3,13(16),14-triene-18,19-dicarboxaldehyde¡]Caseamembrin K, 5¡^¡Brel-(2S,5R,6S,7R,8S,9S,10R, 18S,19R)-2-butanoyloxy-6,7-dihydroxy-18-butanoyloxy-19-acetyloxy-18,19-epoxy-cleroda-3,13(16),14-triene¡]Caseamembrin L, 6¡^¡A¤Îrel-(2S,5R ,6R,8S,9S,10R,18S,19R)-2-O-acetyl-6-butanoyloxy-18,19-acetyloxy-18,19-epoxy-cleroda-3,13(16),14-triene ( 7¡^¡Brel-(2S,5R,6R,8S,9S,10R,18S,19 R)-2-O-acetyl-6,18-dibutanoyloxy-19-acetyloxy-18,19-epoxy-cleroda-3,13(16),14-triene¡]8¡^. It is worthy to mention that this is the first report of the isolation of 1¡Ð6 from a natural source and their derivatives compounds 7 and 8. Compound 1 exhibited moderate cytotoxicity against¡]Hepa59T/VGH¡^ ,¡]KB¡^and ¡]Hela¡^cancer cells , but compound 3 and 4¡B5 show no activity against those cancer cell lines.

As part of the continuing work of the International Cooperative Biodiversity Group (ICBG), plant extracts were received from Madagascar. The extracts were screened for cytotoxicity using the A2780 human ovarian cancer cell line bioassay. The crude extract of Casearia nigrescens was fractionated and yielded five known compounds and one new compound that were cytotoxic. Mass spectrometry and 1D and 2D NMR techniques were used to determine the structure of the isolated compounds. The dichloromethane fraction of Casearia nigrescens was weakly active in the A2780 human ovarian cancer cell line bioassay. Further separation of the dichloromethane fraction resulted in the isolation of five known compounds (casearlucin A, caseamenbrol A, rel-18(S),19(R)-diacetoxy-18,19-epoxy-6(R)-hydroxy-2(S)-(2ξ-methylbutanoyloxy)-5(R),8(S),9(S),10(R)-cleroda-3,13(16),14-triene, casearlucin B, and rel-18(S),19(R)-diacetoxy-18,19-epoxy-2(S)-(2ξ-ethylbutanoyloxy)-5(R),8(S),9(S),10(R)-cleroda-3,13(16),14-triene) and one new compound (casearlucin L). Based on the available literature this was the first investigation of the natural products of Casearia nigrescens. The structure of the known compounds was determined by comparison of the NMR, MS, optical rotation, UV, and IR data with the data found in the literature. The structure of casearlucin L was determined by NMR data and comparison with the NMR data for similar known compounds. / Master of Science

Enxaguatórios bucais podem ocasionar a alteração de cor do elemento dental, devido à desmineralização ocasionada pelo uso prolongado dos mesmos, e consequente aumento da rugosidade superficial. Outros fatores, como o clareamento caseiro e o consumo diário de bebidas ácidas são, da mesma forma, responsáveis pela dissolução do esmalte dental. Buscando superar os efeitos adversos da Clorexidina 0,12%, desenvolveu-se um enxaguatório bucal à base de uma planta medicinal, denominada Casearia sylvestris. O presente estudo teve como objetivo avaliar a ação dos enxaguatórios bucais à base de Casearia sylvestris e Clorexidina 0,12% na cor e rugosidade superfícial do esmalte dental submetido a agente clareador e bebida alimentícia de pH 2,4. Amostras de dentes bovinos foram divididas em 3 grupos (n= 30), de acordo com a solução utilizada: Água destilada, Clorexidina 0,12% e Enxaguatório bucal à base de Casearia sylvestris. Cada grupo foi ainda dividido em subgrupos, de acordo com as categorias (n=10): Grupo controle, dentes clareados e dentes submetidos à imersão em bebida alimentícia ácida. O clareamento caseiro foi realizado com peróxido de carbamida 16%, por 6 horas diárias durante 8 dias, enquanto a imersão em suco de limão (pH 2,4) foi realizada por 2 minutos cada, 1 vez ao dia, durante 6 dias. Posteriormente, os grupos tiveram seus corpos de prova imersos nas respectivas soluções por 2 minutos, 3 vezes ao dia, durante 7 dias. As leituras de cor e rugosidade superficial foram realizadas anteriormente ao período experimental e após a imersão nos enxaguatórios bucais. A análise dos resultados foi realizada através dos testes estatísticos ANOVA - II way e Teste de Tukey 5%. Os dentes submetidos ao clareamento caseiro e à imersão em bebida ácida apresentaram uma maior alteração de cor. As diferentes soluções não apresentaram diferença estatística quanto à alteração de cor. A rugosidade superficial foi maior para o período de 7 dias, sendo que apenas o grupo submetido à imersão em bebida ácida apresentou um aumento significante na rugosidade superficial. Foi possível concluir que apenas o clareamento caseiro e a imersão em bebidas ácidas promoveram alteração na coloração da estrutura dental. Não houve influência dos enxaguatórios bucais utilizados isoladamente ou em associação com os tratamentos na rugosidade superficial. Apenas a imersão em bebida ácida ocasionou aumento na rugosidade superficial. / Mouthwashes can induce the tooth color alteration, due to the desmineralization occured by the prolonged use of them and consequent increase of surface roughness. Another factors, as the home bleaching and the daily consumption of acid drinks are, in the same way, responsible for the dental enamel dissolution. Attempting to overcome the Chlorhexidine 0,12% adverse effects, it was developed a mouthwash containing a medical plant, denominated as Casearia sylvestris. The aim of this study was to evaluate the action of a mouthwash containing Casearia sylvestris and Chlorhexidine 0,12% on color and surface roughness from the dental enamel submitted to bleaching gel and a drink with pH 2,4. Bovine teeth samples were divided in 3 groups (n=30), according to the solution: distillated water, Chlorhexidine 0,12% and a mouthwash containing Casearia sylvestris. Each group was divided in subgroups, according to the categories (n=10): Control group, bleached teeth and teeth immersed in an acid drink. The bleaching procedure was realized with carbamide peroxide 16%, during 6 hours by 8 days, while the acid drink immersion was done during 2 minutes each, once in a day and during 6 days. Posteriorly, the samples were immersed on the respective solutions by 2 minutes, three times at a day, during 7 days. The color and surface roughness lecture were performed before the experimental period and after the immersion on mouthwashes. The data were analyzed by two-way analysis of variance (ANOVA) and Tukey`s test. The teeth submitted to home bleaching and to the immersion in acid drink showed higher color alteration. At the group wich no treatment was applied, the mouthwash containing Casearia sylvestris induce the highest color alteration when compared with the other solutions, and that was statistically equal when the teeth were submitted to different treatments. The surface roughness was higher to the 7 days period, although the only the group submitted to the immersion in acid drink presented a significant enhance on surface roughness. In conclusion, only the bleaching and the immersion in acid drinks promoted a higher color alteration. The mouthwashes did not promoted an alteration on the color of the dental structure. There was no influence from mouthwashes utilized when isolated or in association with the treatments on surface roughness. Only the immersion in acid drink caused an increase on surface roughness.

Orientador: André Gonzaga dos Santos / Resumo: A Casearia sylvestris Swartz apresenta duas variedades: var. sylvestris (típica de Mata Atlântica) e var. língua (típica do Cerrado). As ações anti-inflamatória, antiulcerogênica, antitumoral e antimicrobiana do óleo essencial (OE) das folhas foram comprovadas. A variabilidade química nas plantas é associada a fatores genéticos e ambientais, entretanto, como existem poucos estudos de variabilidade do OE da C. sylvestris, o objetivo foi avaliar o teor e composição química de ambas variedades em locais, períodos e horários diferentes, estabelecendo parâmetros botânicos, físicos e químicos do OE. Neste estudo foram realizadas análises morfoanatômicas e da composição dos solos dos espécimes coletados. O OE foi extraído por hidrodestilação das folhas frescas e folhas secas, para determinação do teor e composição (CG-EM) correlacionando com fatores edáfico-climáticos. Foram realizadas análises físicas e quimiométricas do OE. A morfologia dos troncos e folhas, estômatos e índice de paliçada diferenciaram as variedades. Os resultados da densidade, índice de refração, infravermelho e CCD foram semelhantes entre as variedades e a rotação óptica diferenciou as variedades. As folhas secas e a var. sylvestris possuem maior teor de OE, já o teor de sesquiterpenos oxigenados no OE aumentou com a secagem e extração. Foi verificada variabilidade populacional, intrapopulacional e sazonal no teor de OE. O β-elemeno, α-humuleno, germacreno D, biciclogermacreno, espatulenol, óxido de cariofileno ... (Resumo completo, clicar acesso eletrônico abaixo) / Abstract: Casearia sylvestris Swartz exhibits two varieties: var. sylvestris (typical from Atlantic Fores) and var. língua (typical from Cerrado). The anti-inflammatory, antiulcerogenic, antitumor and antimicrobial activities of essential oil (EO) from leaves were proven. Chemical variability in plants is associated with genetic and environmental factors, however, as there are few studies of C. sylvestris from EO variability, the aim was to evaluate chemical content and composition of both varieties in different places, periods and times, establishing botanical, physical and chemical parameters from EO. In this study, morpho-anatomical and soil analysis from collected specimens were performed. EO was extracted by hydrodistillation from fresh leaves and dry leaves to determine the content and composition (GC-MS) correlating with edaphic-climatic factors. Physical and chemometrics analysis of EO were performed. Morphology of trunk and leaves, stomata and palisade index differentiated varieties. Density, refractive index, infrared and TLC results were similar between varieties and optical rotation differentiated varieties. Dried leaves and var. sylvestris have higher EO content, whereas oxygenated sesquiterpenes content in EO increased with drying and extraction. Population, intrapopulation and seasonal variability in the EO content were verified. β-elemene, α-humulene, germacrene D, bicyclogermacrene, spathulenol, caryophyllene oxide and. humulene epoxide II were the major components in ... (Complete abstract click electronic access below) / Doutor