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Previous issue date: 2016-12-13 / Coordena??o de Aperfei?oamento de Pessoal de N?vel Superior - CAPES / This work describes the isolation and structural determination of special metabolites isolated from leaf and stem of J. wasshauseniana (Acanthaceae), popularly known as a coati tail, which was collected in the Paracambi, RJ; Leaves and stem of T. acutifolia (Malpighiaceae), popularly known as cip?-ro?o, were collected in the Barra do Pira?-RJ and leaf and bark of L. lactescens (Malpighiaceae), popularly known as lain of lold, was collected on the campus of the Federal Rural University of Rio de Janeiro Campus Serop?dica RJ. Some chemical and biological activities of extracts of the last species were evaluated.
Chromatographic fractionation of leaf and stem extracts from the Justicia wasshauseniana (Acanthaceae), from the leaf and stem of Tetrapterys acutifolia (Malpighiaceae), and from the leaves and bark of Lophanthera lactescens (Malpighiaceae) besides analysis of fractions by chromatographic and spectroscopic techniques led to the isolation and identification of constituents of different classes of special metabolites. including new alkaloids from J. wasshauseniana.
From the leaves and stem of J. wasshauseniana were identified a triglyceride with the unsaturated acyl moiety, an unsaturated carboxylic acid, a mixture of steroids (?-Sitosterol, estigmasterol and campesterol) and glycosyl steroids (3-O-?-D-glucopyranosylsitosterol and 3-O-?-D-glucopyranosylstgmasterol), a disaccharide (?-D-glucopyranosyl-O-?-D-fructofuranoside (Sucrose) and the alkaloids acid (N-fenil-o-metileno-O-5)-3-hidroxi-5-carboxy??-lactam, and N(fenil-o-metileno-O-5)-3-hidroxi-5-(carboxilato de 2,3-dihidroxipropionila)-?-lactama), described for the first time in the literature. From the leaves and stem of T. acutifolia were identified a mixture of sitosterol, stigmasterol, 5,6-dihydro-sitosterol. and 5,6-dihydro-20-21,22-23,24-28,25-26-campesterol, ascorbic acid, in addition to sucrose and an ecdysteroid, 2S,3R,5R,9R,10R,13R,14S,17S,20S-2,3,14,20,24,25-hexahidroxicolest-7-en-6-ona (Pinatasterone). The extracts from the leaves and barks of L. lactescens, besides the mixture of sitosterol, stigmasterol and campesterol, was isolated the nortriterpene known as coreolidene. Besides to confirm the structure correction proposed in the literature of this nortriterpene, the absolute stereochemistry was defined as methyl 4R,5R,6R,7S,8S,9S,10S,13R,14S,15S,16R,17S,18R,21S,22S-friedelan-1,2-en-3-carboxy-24- 5- [1-acetoxy-ethylidene] -6,7,15,16-tetracetoxy-18-hydroxy-21,22-oxy-29-methylene-30-carboxylate. The structures were defined through analysis of IR, 1D and 2D NMR, mass spectra and circular dichroism besides some methyl and acetyl derivatives. The methanolic extracts from the stem and leaves of J. wasshausseniana and the methanolic extracts and fractions of the stem and leaves of T. acutilfolia were tested against the free radicals of DPPH. The extract from the stem of J. wasshausseniana was more active than leaf extract. The fraction of hexane from the leaves of T. acutilfolia did not present a good antioxidant activity, a greater activity was observed for the ethyl acetate fraction of stem and leaves of this plant. The pharmacological tests of the antinociceptive and anti-inflammatory potentials of the L. lactescens bark methanolic extract and the methanolic extract of leaves of J. wassahueniana were carried out, in which they showed positive results in the tested activities. / Este trabalho descreve o isolamento e determina??o estrutural de metab?litos especiais isolados de folhas e caule de J. wasshauseniana (Acanthaceae), vulgarmente conhecida como rabo de quati, que foi coletada no Munic?pio de Paracambi, RJ; folhas e caule de T. acutifolia, conhecida vulgarmente como cip?-ru?o, coletado no munic?pio de Barra do Pira?-RJ e L. lactescens (Malpighiaceae), conhecida vulgarmente como Chuva-de-Ouro, coletado no campus da Universidade Federal Rural do Rio de Janeiro Campus Serop?dica RJ. Realizaram-se testes de atividade biol?gica de extratos das duas ?ltimas esp?cies.
O fracionamento cromatogr?fico dos extratos de folhas e caule de Justicia wasshauseniana (Acanthaceae), de folhas e caule de Tetrapterys acutif?lia (Malpighiaceae), de folhas e cascas de Lophanthera lactescens (Malpighiaceae) e an?lise das fra??es atrav?s de t?cnicas cromatogr?ficas e espectrosc?picas conduziu ao isolamento e identifica??o de constituintes de diferentes classes de metab?litos especiais. Das folhas e caule de J. wasshauseniana foram identificados um triglicer?deo com a unidade acila insaturada, um ?cido carbox?lico insaturado, uma mistura dos ester?ides (?-sitostesterol, estigmasterol e campesterol) e a mistura de esteroides glicosilados, 3-O-?-D-glicopiranosilsitosterol e o 3-O-?-D-glicopiranosilestigmasterol, um dissacar?deo, ?-D-glicopiranosil-?-D-frutofuranos?deo (sacarose) e os alcal?ides ?cido-(N-fenil-o-metileno-O-5)-3hidroxi-5-carboxi??-lactama e N(fenil-o-metileno-O-5)-3-hidroxi-5-(carboxilato de 2,3-dihidroxipropionila)-?-lactama) que est?o sendo descritos pela primeira vez na literatura. Dos extratos de folhas e caule de T. acutifolia foram isolados uma mistura dos esteroides, sitostesterol, estigmasterol, 5,6-diidro-sitosterol e 5,6-diidro-20-21,22-23,24-28,25-26-octaidro-campesterol, o ?cido asc?rbico, al?m da sacarose e o ecdisteroide 2S,3R,5R,9R,10R,13R,14S,17S,20S-2,3,14,20,24,25-hexahidroxicolest-7-en-6-ona (Pinatasterona), desta enona que foi convertido em 2,3,24,25-tetraacetato atrav?s de tratamento com anidrido ac?tico e piridina. Dos extratos de folhas e cascas de L. lactescens, al?m da mistura de esteroides sitoesterol, estigmasterol e campesterol, foi isolado o nor-triterpeno conhecido como correolideo que, al?m da confirma??o da corre??o da estrutura registrada na literatura foi proposta a estereoqu?mica absoluta, sendo, entretanto definida como 4R,5R,6R,7S,8S,9S,10S,13R,14S,15S,16R,17S,18R,21S,22S-friedelan-1,2-en-3-carboxi-24-O-metileno-5-[1-acetoxi-etilideno]-6,7,15,16-tetracetoxi-18-hidroxi-21,22-oxi-29-metileno-30-carboxilato de metila. As estruturas foram definidas atrav?s de an?lise de espectros de IV, RMN 1D e 2D, massas e dicro?smo circular e, em alguns casos da prepara??o de derivados. Os extratos metan?licos de caule e de folhas de J. wasshausseniana e os extratos metan?licos e fra??es do caule e folhas de T. acutilfolia foram testados contra os radicais livres de DPPH. O extrato do caule de J. wasshausseniana apresentou melhor atividade do que o extrato de folhas. A fra??o de hexano de folhas de T. acutilfolia n?o apresentou uma boa atividade antioxidante, observando-se uma maior atividade para a fra??o de acetato de etila de caule e folhas. Realizaram-se os testes farmacol?gicos do potencial antinociceptivo e anti-inflamat?rio do extrato metan?lico de cascas de L. lactescens e extrato metan?lico de folhas de J. wassahueniana, no qual apresentaram resultados positivos nas atividades testadas
| Identifer | oai:union.ndltd.org:IBICT/oai:localhost:jspui/2021 |
| Date | 13 December 2016 |
| Creators | Fernandes, Renata Duarte |
| Contributors | Braz Filho, Raimundo, Carvalho, M?rio Geraldo de, Suzart, Luciano Ramos, Oliveira, Marcia Cristina de, Riger, Cristiano Jorge, Martins, Roberto Carlos Campos, Velozo, Leosvaldo Salazar Marques, Maleck, Marize |
| Publisher | Universidade Federal Rural do Rio de Janeiro, Programa de P?s-Gradua??o em Qu?mica, UFRRJ, Brasil, Instituto de Ci?ncias Exatas |
| Source Sets | IBICT Brazilian ETDs |
| Language | Portuguese |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/doctoralThesis |
| Format | application/pdf |
| Source | reponame:Biblioteca Digital de Teses e Dissertações da UFRRJ, instname:Universidade Federal Rural do Rio de Janeiro, instacron:UFRRJ |
| Rights | info:eu-repo/semantics/openAccess |
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