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 No. of bitstreams: 1 2016_tese_lmsousa.pdf: 24821219 bytes, checksum: 3899ad5625838e46813ab9727472fabc (MD5) / Approved for entry into archive by Jairo Viana (jairo@ufc.br) on 2016-12-27T16:16:42Z (GMT) No. of bitstreams: 1 2016_tese_lmsousa.pdf: 24821219 bytes, checksum: 3899ad5625838e46813ab9727472fabc (MD5) / Made available in DSpace on 2016-12-27T16:16:42Z (GMT). No. of bitstreams: 1 2016_tese_lmsousa.pdf: 24821219 bytes, checksum: 3899ad5625838e46813ab9727472fabc (MD5) 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.

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 2017-01-24T21:20:20Z No. of bitstreams: 1 2016_tese_lmsousa.pdf: 24821219 bytes, checksum: e022dc323cde53950dcc209fb460ecf4 (MD5) / Approved for entry into archive by Jairo Viana (jairo@ufc.br) on 2017-01-26T20:20:52Z (GMT) No. of bitstreams: 1 2016_tese_lmsousa.pdf: 24821219 bytes, checksum: e022dc323cde53950dcc209fb460ecf4 (MD5) / Made available in DSpace on 2017-01-26T20:20:52Z (GMT). No. of bitstreams: 1 2016_tese_lmsousa.pdf: 24821219 bytes, checksum: e022dc323cde53950dcc209fb460ecf4 (MD5) 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 g/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 g/ 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 g/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.