Este trabalho descreve a prospecÃÃo quÃmica do extrato etanÃlico das folhas de Acnistus arborescens (Solanaceae). Esse estudo resultou no isolamento e caracterizaÃÃo de vÃrios
metabÃlitos secundÃrios, incluindo as vitafisalinas M, N, O, F (epÃmeros 18R e 18S) e 2,3-desidro-F (epÃmeros 18R e 18S), alÃm de quatro novas vitafisalinas, sendo trÃs cloradas. As
estruturas das novas vitafisalinas foram estabelecidas como: rel-(17S, 20R, 22R)-6a-cloro-18S-etÃxi-18,20-epÃxi-4b,5b-dihidrÃxi-1-oxo-vita-2,24-dienolido, rel-(17S, 20R, 22R)-6a-
cloro-18R-etÃxi-18,20-epÃxi-4b,5b-dihidrÃxi-1-oxo-vita-2,24-dienolido, rel-(17S, 20R, 22R)-6-cloro-18,20-epÃxi-4,5-diidrÃxi-18-metÃxi-1-oxovita-2,24-dienolido e rel-
(17S,20R,22R)-5,6:18,20-diepÃxi-3,18-dietÃxi-4-hidrÃxi-1-oxovita-24-enolido. Adicionalmente a estes compostos, foram tambÃm isolados dois flavonÃides, canferol e
quercetina, e uma ceramida, cuja estrutura foi determinada como (2R,3S,4S,16E)-2[(2âR)-2â-hidroxiheneicosanoilamino]-nonadec-16-eno-1,3,4-triol. Foi realizado ainda um estudo
de fragmentaÃÃo de massas com as vitafisalinas isoladas, para a construÃÃo de uma minibiblioteca de padrÃes de fragmentaÃÃo, a fim de reconhecer estes compostos ou anÃlogos em outros extratos. Com isso, foi possÃvel identificar oito novas vitafisalinas (C-H, J e K) numa fraÃÃo de elevado potencial citotÃxico (PPTC38), alÃm de realizar um estudo
qualitativo da composiÃÃo quÃmica dos extratos obtidos das folhas de A. arborescens cultivada, onde foi possÃvel identificar a vitafisalina F como constituinte majoritÃrio na fraÃÃo analisada. As tÃcnicas analÃticas utilizadas na elucidaÃÃo estrutural dos compostos isolados foram IV, EMAR e RMN 1H e 13C (1D e 2D), enquanto a tÃcnica utilizada no estudo de fragmentaÃÃo, bem como na anÃlise qualitativa das fraÃÃes foi a cromatografia lÃquida acoplada à espectrometria de massas de alta resoluÃÃo (CLAE-EM). / In this study herein, describes the chemical prospect of ethanol extract from leaves of Acnistus arborescens (Solanaceae). Therefore, this study resulted in the isolation and characterization of several secondary metabolites, including the withaphysalins M, N, O, F (epimers 18R and 18S) and 2,3-dehydro-F (epimers 18R and 18S), as well as four new withaphysalins, being three chlorinated. Their structures were established as new withaphysalins: rel-(17S, 20R, 22R)-6-chloro-18S-ethoxy-18,20-epoxy-4,5-dihidroxy-1-oxo-witha-2,24-dienolide, rel-(17S, 20R, 22R)-6-chloro-18R-ethoxy-18,20-epoxy-4,5-dihidroxy-1-oxo-witha-2,24-dienolide, rel-(17S, 20R, 22R)-6α-chloro-18,20-epoxy-4β,5β-dihidroxy-18α-methoxy-1-oxo-whita-2,24-dienolide e rel-(17S,20R,22R)-5β,6β:18,20-diepoxy-3β,18α-diethoxy-4β-hidroxy-1-oxo-witha-24-enolide. Furthermore, two flavonoids, kaempferol and quercetin, were also isolated and a ceramide, whose structure was determined as rel-(2S,3S,4R,16E)-2-[(2âR)-2â-hydroxynonadecanoylamino]-heneicosadec-16-ene-1,3,4-triol. A study was also carried out about fragmentation with withaphysalins isolated with the objective to construct a mini-library with fragmentation patterns, in order to recognize the withaphysalins or similar compounds in other extracts. Hence, it was possible to identify eight new withaphysalins (C-H, J and K) in a fraction of high cytotoxic potential (PPTC38), and perform a qualitative study of the chemical composition in extracts from leaves of A. arborescens, whereby it was possible to identify the withaphysalin F, as a major constituent from the fraction duly analyzed. The analytical techniques used in the structural elucidation of isolated compounds were IR, MSHR and 1H and 13C NMR (1D and 2D), where as the technique used in the study of fragmentation, as well as the qualitative analysis of the fractions, was the liquid chromatography-mass spectrometry high resolution (HPLC-MS).
| Identifer | oai:union.ndltd.org:IBICT/oai:www.teses.ufc.br:5044 |
| Date | 02 December 2010 |
| Creators | Ana Isabel Vitorino Maia |
| Contributors | OtÃlia DeusdÃnia Loiola Pessoa, Mary Anne Sousa Lima, Marcos Carlos de Mattos, Selene Maia de Morais, Edson Rodrigues Filho |
| Publisher | Universidade Federal do CearÃ, Programa de PÃs-GraduaÃÃo em QuÃmica, UFC, BR |
| 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 UFC, instname:Universidade Federal do Ceará, instacron:UFC |
| Rights | info:eu-repo/semantics/openAccess |
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