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Doctoral Thesis
DOI
10.11606/T.46.2018.tde-12112018-161216
Document
Author
Full name
Ana Paula Danelutte
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 2001
Supervisor
Committee
Kato, Massuo Jorge (President)
Cavalheiro, Alberto Jose
Bechara, Etelvino Jose Henriques
Gruber, Jonas
Young, Maria Claudia Marx
Title in Portuguese
Estudo do metabolismo secundário em Piper crassinervium (Piperaceae)
Keywords in Portuguese
Aristolactamas
Piper crassinervium
Produtos naturais
Química orgânica
Suspensões celulares
Abstract in Portuguese
Este trabalho descreve o estudo do metabolismo secundário em folhas diferenciadas e em suspensões celulares de Piper crassinervium (Piperaceae). Este estudo foi monitorado pela análise do extrato de folhas por CLAE, assim como pela comparação entre os diferentes tecidos desta espécie (folhas, caule e raízes). Do extrato das folhas foram isoladas duas flavanonas, duas hidroquinonas preniladas e uma hidroquinona com um endoperóxido na cadeia lateral. A análise do óleo volátil das folhas através de CG e CG-EM, revelou a presença de trinta e seis componentes, sendo majoritários o germacreno-D (10,05%) seguido por β-cariofileno (9,91 %) e 6-metil-5-hepten-2-ona (7,47%). Todas as substâncias isoladas foram submetidas ao ensaio antifúngico bioautográfico contra Cladosporium sphaerospermun, sendo que as flavanonas, as duas hidroquinonas e o óleo volátil mostraram-se ativos. As suspensões celulares foram desenvolvidas a partir de calos, iniciados a partir de ápices, em meio B5 modificado, contendo ácido naftalenoacético (ANA) e 6-benzilamino purina (BAP) como reguladores de crescimento. As células não produziram flavonóides, mas alcalóides do tipo aristolactamas, que são parcialmente excretados para o meio de cultura. A curva de crescimento estabelecida para as células foi analisada quanto à atividade específica da fenilalanina amônia-liase (PAL), à variação do pH e o acúmulo dos alcalóides. Alguns experimentos de eliciação demonstraram respostas positivas face ao uso de luz UV, adição de L-fenilalanina e uso de extratos de levedura.
Title in English
Study of the secondary metabolism in Piper crassinervium (Piperaceae)
Keywords in English
Aristolactamas
Cellular suspensions
Natural products
Organic chemistry
Piper crassinervium
Abstract in English
The present work studies the secondary metabolism in leaves of Piper crassinervium (Piperaceae) and in its cell suspension culture as well. The profile of secondary compounds in differenciatted and undifferenciated tissues were evaluated by HPLC. The aerial parts of Piper crassinervium yielded two flavanones and three prenylated hydroquinones, one having an endoperoxide group in the side chain. The analysis of the volatile oil of Piper crassinervium by GC-MS allowed the identification of 36 compounds, germacrene-D (10,05%), β-cariofilene (9,91 %) and 6-methyl-5-heptene-2-one (7,47%) being detected as the major ones. Ali isolated substances were evaluated using a bioautography technique against the fungus Cladosporium sphaerospermun. The isolated flavanones, two hydroquinones and the essential oil were found to be active against the fungus. The cell suspensions had their growth curve established on basis of the dry weight and pH variations. The cells were showed to accumulate several aristolactams alkaloids instead. Determinations of these alkaloids by HLPC indicated that the cells excreted them partially to the culture media. Determinations of specific activity of PAL and concentration of alkaloids during the growth cycle were further performed. Additional experiments revealed that UV light and the addition of either phenylalanine or yeast extract cause elicitation response with increased production of alkaloids.
 
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Publishing Date
2018-11-13
 
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