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http://hdl.handle.net/1843/30203| Type: | Tese |
| Title: | Estudo fitoquímico e avaliação da atividade biológica de Tontelea Micrantha Mart. ex Schult. (Celastraceae) |
| Authors: | Fernanda Lopes Ferreira |
| First Advisor: | Lucienir Pains Duarte |
| First Co-advisor: | Lúcia Pinheiro Santos Pimenta |
| First Referee: | Dâmaris Silveira |
| Second Referee: | Lourdes Campaner dos Santos |
| Third Referee: | Diogo Montes Vidal |
| metadata.dc.contributor.referee4: | Rosemaire Brondi Alves |
| Abstract: | O estudo fitoquímico de folhas, galhos e raízes de Tontelea micrantha levou ao isolamento/identificação de 31 substâncias. Foram isolados 20 triterpenos pentacíclicos: friedelina (TM03), 3β-friedelinol (TM04), ácido 3,4-seco-friedelanoico (TM05), 28-hidroxifriedelan-3-ona (TM06), friedelan-3,21-diona (TM13), 21βhidroxifriedelan-3-ona (TM14), 21α-hidroxifriedelan-3-ona (TM15), 30hidroxifriedelan-3-ona (TM16), 3-oxo-friedelan-28-al (TM17), friedel-1-en-3,21-diona (TM18), friedelan-1,3,21-triona (TM19), ácido 3-oxo-friedelan-28-oico (TM21), 28,29di-hidroxifriedelan-3-ona (TM22), 21α,30-di-hidroxifriedelan-3-ona (TM23), 28,30-dihidroxifriedelan-3-ona (TM24), tingenina B (TM27), netzahualcoiona (TM28), netzahualcoiondiol (TM29), salaquinona A (TM30) e o ácido ortosfênico (TM31). Também foram isolados 4 flavonoides: 3-O-[α-L-ramnopiranosil(1→2)][α-Lramnopiranosil(1→6)]-β-D-glicopiranosídeo de quercetina (TM10), rutina (TM11), epiafzelequina-(4β→8)-epicatequina (TM12) e a epicatequina (TM25). Além disso foram isolados o esteroide β-sitosterol (TM20) e seu derivado glicosilado, o 3βglicosil-β-sitosterol (TM08), um sesquiterpeno de esqueleto di-hidro- β-agarofurano, 2,3,6,15-tetra-acetoxi-1,9-dibenzoiloxi-8-oxo-β-agarofurano (TM26). Um carboidrato, o dulcitol (TM09), uma mistura de ácidos graxos (TM07), o polímero guta percha (TM01) e o esqualeno (TM02) também foram isolados. As substâncias TM18, TM19 e TM26 são inéditos. O estudo biológico consistiu da avaliação da atividade antimicrobiana (antibacteriana e antifúngica), da atividade antiviral contra virus Zika e virus Mayaro, da atividade citotóxica e da atividade de inibição da enzima Na+,K+ATPase cardíaca. O extrato metanólico das folhas apresentou atividade anti-Mayaro pronunciada. Os extratos das folhas e galhos mostraram atividade anti-Zika, sendo que o extrato acetato etílico das folhas e o extrato metanólico das folhas apresentaram inibição da penetração viral em concentrações mais baixas do que 15,6 µg/mL. As substâncias TM11, TM21, TM25, TM26, TM29 e o óleo extraído das sementes apresentaram atividade citotóxica moderada frente às linhagens de células de leucemia mieloide aguda (THP-1), mieloide crônica (K562) e células de carcinoma mamário (MDA-MB-231). |
| Abstract: | Phytochemical study and biological evaluation of Tontelea micrantha Mart. ex Schult. (Celastraceae) The phytochemical study of leaves, branches and roots of Tontelea micrantha resulted in the isolation/identification of 31 compounds. Among them 20 are pentacyclic triterpenes: friedelin (TM03), 3β-friedelinol (TM04), 3,4-seco-friedelanoic acid (TM05), 28-hydroxyfriedelan-3-one (TM06), friedelan-3,21-dione (TM13), 21βhydroxyfriedelan-3-one (TM14), 21α-hydroxyfriedelan-3-one (TM15), 30hydroxyfriedelan-3-one (TM16), 3-oxo-friedelan-28-al (TM17), friedel-1-en-3,21-dione (TM18), friedelan-1,3,21-trione (TM19), 3-oxo-friedelan-28-oic acid (TM21), 28,29dihydroxyfriedelan-3-one (TM22), 21α,30-dihydroxyfriedelan-3-one (TM23), 28,30dihydroxyfriedelan-3-one (TM24), tingenin B (TM27), netzahualcoyone (TM28), netzahualcoyondiol (TM29), salaquinone A (TM30) and the orthosphenic acid (TM31). Four flavonoids were also isolated: 3-O-[α-L-rhamnopyranosyl (1 → 2)][α-Lrhamnopyranosyl (1→6)]-β-D-glucopyranoside of quercetin (TM10), rutin (TM11), epiafzelechin-(4β → 8)-epicatechin (TM12) dimer and epicatechin (TM25). In addition, the steroid, β-sitosterol (TM20) and its glycosylated derivative, 3-Oβ -D-glicosil-β-sitosterol (TM08), and a β-di-hydroagarofuran sesquiterpene 2,3,6,15-tetra-acetoxy1,9-dibenzoyloxy-8-oxo-β-agarofuran (TM26) were isolated. A carbohydrate, dulcitol (TM09), a mixture of fatty acids (TM07), the gutta percha (TM01) polymer and squalene (TM02), a precursor of pentacyclic triterpenes, were also isolated. The substances TM18, TM19 e TM26 are new compounds. The study of the biological activity consisted of the evaluation of the antimicrobial activity (antibacterial and antifungal), of the antiviral activity against Zika virus and Mayaro virus, of the cytotoxic activity and the study of the inhibition activity of the cardiac Na+,K+-ATPase enzyme. The methanolic leaf extract showed pronounced anti-MAYV activity. Leaf and branch extracts showed anti-ZIKV activity, with the ethyl acetate and methanolic leaf extracts inhibiting viral penetration at lower concentrations of 15.6 μg/mL. The compounds TM11, TM21, TM25, TM26, TM29 and the seed oil showed moderate cytotoxic activity against the mammary carcinoma cells (MDA-MB-231) and the acute (THP-1) and chronic myeloid leukemia cells (K562). |
| Subject: | Química orgânica Produtos naturais Celastraceae Terpenios Produtos de ação antimicrobiana Agentes antivirais Atividade antifúngica Agentes antineoplásicos |
| language: | por |
| metadata.dc.publisher.country: | Brasil |
| Publisher: | Universidade Federal de Minas Gerais |
| Publisher Initials: | UFMG |
| metadata.dc.publisher.department: | ICX - DEPARTAMENTO DE QUÍMICA |
| metadata.dc.publisher.program: | Programa de Pós-Graduação em Química |
| Rights: | Acesso Aberto |
| URI: | http://hdl.handle.net/1843/30203 |
| Issue Date: | 9-Aug-2019 |
| Appears in Collections: | Teses de Doutorado |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
| Estudo fitoquímico e avaliação da atividade biológica de Tontelea micrantha.pdf | Aberto | 16.21 MB | Adobe PDF | View/Open |
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