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METABOLISMO SECUNDÁRIO EM TECIDOS DIFERENCIADOS E SUSPENSÕES CELULARES DE Piper Cernuum Vell

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METABOLISMO SECUNDÁRIO EM TECIDOS DIFERENCIADOS E SUSPENSÕES CELULARES DE Piper Cernuum Vell B IB i. VOTECÁYJ Á.Mi V~ INSTITUTO DE QU(MICA Universidade de São Pa~o l0°Jif:, UNIVERSIDAQE DE SÃO PAULO INSTITUTO DE QUÍMICA METABOLISMO SECUNDÁRIO EM TECIDOS DIFERENCIADOS E SUSPENSÕES CELULARES DE Piper cernuum Vell. MARA BEATRIZ COS T ANTIN TESE DE DOUTORADO ORIENTADOR: Dr. MASSUO JORGE KATO SÃO PAULO 2001 INSTITUTO DE QUÍMICA , Ulllwersidlldo da São Paolê 'Metabolismo Secundário em Tecidos Diferenciados e Suspensões Celulares de Piper cernuum Vell''' MA8A ••ara1z COMSl'AMl'IM Tese de Doutorado submetida ao Instituto de Química da Universidade de São Paulo como parte dos requisitos necessários à obtenção do grau de Doutor em Ciências - Área: Química Orgânica. Aprovada por: Prof. Dr. MASSUO JORGE KATO IQ - USP (Orientador e Presidente) Profa. Ora. CLELIA FERREIRA TERRA IQ - USP Prof. Dr. JOSEF W ILHELM BAADER IQ - USP Profa. Ora. DEBORAH YA RA ALVES CURSINO DOS SANTOS 1B - USP Profa. Ora. MA RCIA REGINA BRAGA IBt - SP BISLIOTECJ\ SÃO PAULO INSTITUTJ DE QU1MICA 30 DE OUTUBRO 200 1. Unlvorsldad• do São PIJIIII, "Plant biochemistry in its most exclusiveform might consider only those aspects ofthe chemical operations ofplants that are unique to plants. Thus, photosynthesis, synthesis of cellulosic cell walls, lignification, the metabolism ofsecondary compounds, and systems for the mass movement ofwater and photosynthates would constitute the bulk ofplant biochemistry. However, plant biochemistry in its most inclusive form would consider all chemical operations that occur in plants. Jf, for example, a particular metabolic pathway appears to be the sarne in plants and mammals, it is still a part ofplant biochemistry. Plant biochemistry in its most inclusive form not only must include the new concepts and methods ofbiochemistry but also must recognize that these concepts and methods also apply to andlor are derivedfrom physiology, cell biology, molecular biology and genetics. Progress toward this understanding is driven largely by our intellectual curiosity. " JOSEPH E. V ARNER, 1995 Try to realize it's ali within yourself, no one else can make you change and to see you 're really only very small and life jlows on within you and without you. When you 've seen beyond yourself then you may find piece of mind is waiting there and the time will come when you see we 're ali one and life jlows on within you and without you. G. HARRINSON, 1967 AOS MEUS AMORES: J . ELPÍDIO, LINA, BETO, JÚNIOR E MARTIN AGRADECIMENTOS Ao Prof. Dr. Massuo J. Kato por conceder-me a oportunidade de participar do seu grupo de pesquisa e desenvolver esta tese e também pela compreensão e confiança no meu trabalho. Ao Prof. Dr. Paulo R. H. Moreno pelas sugestões apresentadas durante o trabalho experimental e auxílio na discussão dos resultados. Aos Prof. Dr. Pio Colepicolo Neto, alunos (em especial: Patrícia Lopes) e funcionários de seu laboratório pela gentileza em cooperar, deixando-nos à disposição aparelhos e reagentes necessários ao andamento deste trabalho. Aos Prof. Dr. Vicente P. Emerenciano e Marcelo J. P. Ferreira pelo apoio prestado durante a elaboração final desta tese. Às Renata P. Limberger e Profa. Dra. Amélia T. Henriques pela análise em CG-EM do óleo volátil. À Profa. Dra. Mitsuko T. Ohara pelo auxílio durante a análise microbiológica do óleo volátil. Ao Dr. Guillermo Delgado pela indução de calos e estabelecimento das suspensões celulares de Piper cernuum. Aos funcionários da Central Analítica Fernando M. de Oliveira e Márcio N. Wandermuren. Ao colegas e funcionários do B 11 T pela agradável convivência diária, além da ajuda, e um obrigada especial para o Leandro R. Latorre, Sérgio M. Nunomura, Karine C. da Silva e José Antônio Joaquim. Aos amigos Ana Paula Danelutte, Ana Paula Santos, Alessandra, Angélica, Antônio Jedson, Fátima, Francimeiry, Isabel, Marcelo, Melânia, Patrícia, Roberto e Sérgio Galdino pelo carinho e atenção. Aos Felipes, Elaine e Luciana pela ajuda indispensável oferecida durante os momentos iniciais de permanência nesta cidade. Aos Drs. Antônio, Elza e Rodrigo, Gabriel, Davi e Pedro pela hospedagem, paz, afeto e alegria que me proporcionaram nos momentos finais da execução desta tese. Às famílias Steppe, Fantucci, Passetto, Cattani & Costantin pelo apoio constante. A todos que anônimos colaboraram de alguma maneira na execução desta tese. A CAPES pela bolsa concedida. RESUMO O objetivo deste trabalho foi estudar o metabolismo secundário de Piper cernuum (Piperaceae) através do isolamento e caracterização dos principais produtos acumulados e a associação com a atividade enzimática da PAL (fenilalanina-amônia-liase) na planta diferenciada (adulta e plântulas) e nas suspensões celulares. Das folhas foram isolados diversos derivados do ácido cinâmico e a lignana cubebina. Entretanto, na análise do óleo volátil das folhas, através de CG-EM, observou-se somente a presença de mono- e sesquiterpenos, sendo que os mais abundantes foram biciclogermacreno (21,88%) e P­ cariofileno (20,60%). O óleo apresentou atividade inibitória contra Staphylococcus aureus e Candida albicans. As suspensões celulares foram caracterizadas quanto à produção de biomassa, variação de pH e captação de açúcar. Os principais metabólitos foram isolados e caracterizados como sendo tiramina e dopamina que foram quantificadas por cromatografia líquida de alta eficiência através de seus derivados dansilados. As atividades da PAL nas plântulas cultivadas in vitro foram superiores às das plântulas cultivadas em campo e observou-se uma oscilação rítmica da sua atividade enzimática com picos às 6 e 18 horas . ,, II ABSTRACT The aim of this work was to investigate the secondary metabolism of Piper cernuum (Piperaceae) by means of isolation and characterization of major secondary compounds accumulated in association to the enzymatic activity of PAL in the differentiated plant material (adult and seedlings) and cell suspension cultures. The major compounds in leaves were derivatives of cinnamic acid and the lignan cubebin. Nevertheless, the analysis of essential oil from leaves by GC-MS indicated the presence of only mono- and sesquiterpenes, among which bicyclogermacrene (21.88%) and P-cariophyllene (20.60%) were the predominant ones. The oil was active against Staphylococcus aureus and Candida albicans. The cell suspension cultures had their growth cycle characterized by means of evaluation of biomass production, pH variation and sugar uptake. The major secondary compounds in the cells were characterized as tyramine and dopamine which were quantified by HPLC as their dansylated derivatives. The PAL activities in the seedlings cultivated in vitro were higher than those in the seedlings growing in field conditions and a rithymic oscillation of enzyme activity was clearly observed with peaks at 6a.m. and 6p.m. III SUMÁRIO 1. Introdução geral............................................................................ ............................. O1 1.1 Metabolismo das plantas................ ...................... .... ... ..... ......... .. ... ................ ..... O1 1.2 Cultura de células vegetais............................... ................. .. ...... .... ........ ..... ....... 03 l .3 Piper cernuum. ............ ............................... .. .. ............. ............ ................... .. ...... 05 1.4 Objetivos.................... ............. ... ......................................................................... 06 2. Revisão da Literatura.......... ... ...... ....... .................... .. .. ........ ... ..... ....... .. ........... ... ........ 07 2.1 Introdução geral: gênero Piper. ............ .... ........... .. ... .. ........ .. ...... ........... ....... ..... 07 2.2 Química do gênero Piper....... .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. 09 2.3 Atividade biológica e uso na medicina popular de espécies do gênero Piper .. ..... ... ... ...... ............... .. ..................... .. ............................... .. ....................... 37 3. Material e métodos................................... .. ................................... .. ...... ... ............. .... 52 3 .1 Material biológico. .. ......................... .... ... .. ......................... ........ ................. ........ 52 3 .1.1 Material vegetal............. .......... .. ... ... .... ..... ...... .. .... ... ... .............. ..... ..... .. ... 52 3 .1.2 Obtenção de plântulas estéreis de P. cernuum por germinação de sementes............... ......................................... ... ........................................ 52 3.1.3. Cultura de calos ............... ........ ... ..... ... .. ... ..... ...... .... ........................... ..... .. 52 3 .1.4 Suspensões celulares..... .......................... ....... ..... .. ...... .............................. 53 3.2 Tamanho de inóculo .. ... .................... ...... ....... .... ....... .. .. ..... .. .... ... ...... .. .... .. ........... 53 3.3 Determinação da curva de crescimento das suspensões celulares................... ... 53 3 .4 Determinação dos valores de pH..... .. ........ ... ... ... ....... ........................ .. ............... 54 3.5 Determinação das matérias fresca e seca das suspensões celulares................... 54 3.6 Doseamento de açúcares no meio de cultura.. .. .... ... ... .................... ....... ..... ... ..... 54 3.7 Determinação da atividade específica da PAL..................... .. ............. ..... .......... 55 3.7.1 Extração de proteína para ensaio enzimático...... ..... ..... .... .. .... ... ..............
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