SOUSA, Leôncio Mesquita de. Estudo químico e avaliação biológica de Phanera glabra (Jacq.) Vaz & Bauhinia ungulata L. (FABACEAE). 2016. 263 f. Tese (Doutorado em Química)-Universidade Federal do Ceará, Fortaleza, 2016. / Submitted by Aline Mendes (alinemendes.ufc@gmail.com) on 2016-12-21T20:43:17Z
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Previous issue date: 2016 / This paper describes the chemical and biological study of species Phanera glabra
(Jacq.) Vaz and Bauhinia ungulata L. The chemical composition of essential oil from
leaves of B. ungulata, obtained by hydrodistillation, was analysed by gas
chromatography-mass spectroscopy (GC-MS) and gas chromatography-flame
ionization detector. Twenty-two constituents were identified representing 85.90% of
the total composition: Caryophyllene oxide (22.99%), (E)-caryophyllene (14.53%) and
α-copaene (7.17%) were the major constituents. Larval bioassay against Aedes
aegypti of B. ungulata essential oil showed LC50 value of 75.12 ± 2.82 µg/mL. The
cytotoxic effect against four human tumor cell lines HL-60, MCF-7, NCI-H292 and
HEP-2 was evaluated, showing IC50 values of 10.57; 22.25; 23.11 and 26.56 µg/ mL,
respectively. The study of the non-volatile constituents was initiated with the
preparation of the hexane and ethanol extracts from stems of P. glabra. The
chromatographic fractionation of these extracts allowed the isolation of lupenone
(PG–1), the mixture of sitosterol and stigmasterol (PG–2), 4'-hydroxy-7-
methoxyflavone (PG–3), 3',7-dimethoxy-4'-hydroxyflavone (PG–4) and 5,5'-
dihydroxy-2',3,7-trimethoxyflavone (PG–5). Taraxerol (BU–1), betulinic acid (BU–2),
taraxerone (BU–3), glutinol (BU–4), the mixture of sitosterol and stigmasterol (BU–5),
pacharin (BU–6), naringenin (BU–7) and eriodictyol (BU–8), liquiritigenin (BU–9),
guibourtinidol (BU–10) and fisetinidol (BU–11) were obtained from the extracts from
stems of B. ungulata; while 3,5-dimethoxy-4-methyl-2’-hydroxybibenzyl (BU–12) and
3,5-dimethoxy-2’-hydroxybibenzyl (BU–13) were isolated from the ethanol extract of
the roots. The structures of the compounds were elucidated by spectroscopic
methods as IR, MS, 1D and 2D NMR, and by comparison with previously reported
data in the literature. It's worth noting that BU–12 is unprecedented in the literature
and the 13C NMR data of BU–13 are reported for the first time in this work. The
cytotoxicity of BU–12 has been evaluated against four human cancer cell lines,
showing IC50 values of 4.3 and 6.5 µg/mL against pro-myelocytic leukemia (HL-60)
and cervical adenocarcinoma (HEP-2) cell lines, respectively. / O presente trabalho relata o estudo químico e biológico das espécies Phanera
glabra (Jacq.) Vaz e Bauhinia ungulata L. A composição química do óleo essencial
das folhas de B. ungulata, obtido por hidrodestilação, foi determinada e quantificada
por cromatografia gasosa acoplada à espectrometria de massas (CG-EM) e detector
de ionização por chama (CG-DIC), sendo, portanto, identificado 85,90% dos seus
constituintes: Óxido de cariofileno (22,99%), (E)-cariofileno (14,53%) e α-copaeno
(7,17%) foram os constituintes majoritários. O óleo essencial teve sua atividade
larvicida avaliada sobre Aedes aegypti, sendo obtido um valor de CL50 igual a 75,12
µg/mL. A atividade citotóxica do OEBU foi realizada sobre quatro linhagens tumorais
humanas HL-60, MCF-7, NCI-H292 e HEP-2, através do método do MTT. O estudo
dos componentes não voláteis foi iniciado com a preparação dos extratos hexânico e
etanólico dos caules de P. glabra. O fracionamento cromatográfico destes extratos
permitiu o isolamento de lupenona (PG–1), mistura de sitosterol e estigmasterol
(PG–2), 4’-hidroxi-7-metoxiflavana (PG–3), 3’,7-dimetoxi-4’-hidroxiflavana (PG–4) e
5,5'-dihidroxi-2',3,7-trimetoxiflavona (PG–5). Taraxerol (BU–1), ácido betulínico (BU–
2), taraxerona (BU–3), glutinol (BU–4), mistura de sitosterol e estigmasterol (BU–5),
pacharina (BU–6), naringenina (BU–7), eriodictiol (BU–8), liquiritigenina (BU–9),
guibourtinidol (BU–10) e fisetinidol (BU–11) foram isolados a partir dos extratos dos
caules de B. ungulata; enquanto do extrato etanólico das raízes de B. ungulata
foram isolados 3,5-dimetoxi-4-metil-2’-hidroxibibenzil (BU–12), substância inédita na
literatura, e 3,5-dimetoxi-2’-hidroxibibenzil (BU–13) cujos dados de RMN 13C são
descritos pela primeira vez neste trabalho. As estruturas dos compostos foram
elucidadas através de técnicas espectroscópicas tais como IV, EM, RMN 1D e 2D, e
por comparação com dados descritos na literatura. O bibenzil 3,5-dimetoxi-4-metil-2’-
hidroxibibenzil mostrou atividade citotóxica significativa contra as linhagens celulares
humanas HL-60 e HEP-2 com valores de IC50 de 4,3 e 6,5 µg/mL, respectivamente.
| Identifer | oai:union.ndltd.org:IBICT/oai:www.repositorio.ufc.br:riufc/21448 |
| Date | January 2016 |
| Creators | Sousa, Lôncio Mesquita de |
| Contributors | Santiago, Gilvandete Maria Pinheiro |
| Source Sets | IBICT Brazilian ETDs |
| Language | Portuguese |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/doctoralThesis |
| Source | reponame:Repositório Institucional da UFC, instname:Universidade Federal do Ceará, instacron:UFC |
| Rights | info:eu-repo/semantics/openAccess |
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