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Doctoral Thesis
DOI
https://doi.org/10.11606/T.46.1999.tde-13062024-120548
Document
Author
Full name
Luciana Retz de Carvalho
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 1999
Supervisor
Committee
Roque, Nidia Franca (President)
Di Vitta, Claudio
Moreno, Paulo Roberto Hrihorowitsch
Vilegas, Wagner
Young, Maria Claudia Marx
Title in Portuguese
A Química de Vidalia obtusiloba (= Osmundaria obtusiloba) [Rhodophyta - Ceramiales] e suas implicações sistemáticas
Keywords in Portuguese
Compostos aromáticos
Compostos halogenados
Produtos naturais
Abstract in Portuguese
O presente trabalho teve como objetivos realizar o estudo da rodoficea marinha Vidalia obtusiloba (Osmundaria obtusiloba), visando o isolamento e a identificação ou elucidação estrutural de seus metabólitos principais e avaliar estas substâncias segundo critérios quimiossistemáticos, buscando situá-los em padrões já estabelecidos. De extratos obtidos com solventes de diferentes polaridades foram isoladas, através de técnicas cromatográficas, nove substâncias, sendo quatro delas inéditas. São elas fenóis e oligofenóis bromados, com e sem grupos sulfatos, além de esteróide, glicerídeo e glicosídeo aminado. As análises estruturais foram efetuadas com base em dados espectroscópicos de RMN 1H e 13C, incluindo experimentos bidimensionais, em dados obtidos dos espectros de massas, de infravermelho, e análise elementar e no caso do glicosídeo aminado, em difração de raios X. Do ponto de vista quimiossistemático, as substâncias enquadram-se nos padrões esperados para rodofíceas marinhas. Através de um levantamento bibliográfico descobriu-se que o padrão quimiotaxonômico que correlaciona a ocorrência de determinados metabólitos primários com a de metabólitos secundários, ou seja, que relaciona a ocorrência do(s) floridosídeo(s) com a de terpenos e a do digeneasídeo com a de fenóis bromados é uma constante nestas macro algas, enquadrando-se a V. obtusiloba neste último caso.
Title in English
A Química de Vidalia obtusiloba (= Osmundaria obtusiloba) [Rhodophyta - Ceramiales] e suas implicações sistemáticas
Keywords in English
Compostos aromáticos
Compostos halogenados
Produtos naturais
Abstract in English
The present work has as its objective to carry out a study of the marine red alga Vidalia obtusiloba (Osmundaria obtusiloba), with intente to isolate, identify and/or elucidate the structure of its principal metabolites and to evaluate these substances according to chemosystematic criteria so as to situate them within established patterns. From extracts obtained through the use of solvents of diferente polarities, we were able to isolate through chromatographic techniques nine substances, of which 4 had not been seen before. These are phenols and bromate oligophenols, with and without sulphate groups, in addition to a steroid, a glyceride and an amine glycoside. Structural analyses were carried out based on RMN 1H and 13C spectroscopic data, including bidimensional experiments, on data obtained through infrared mass spectrum and elementary analysis. In the case of the amine glycosides, these were based on X-ray diffraction. F rom the chemosystematic point of view, these substances fall into the expected pattems for marine rhodophytes. Through bibliographical research we were able to find that the chemotaxonomic patterns that correlate the occurrence of certain primary metabolites with secondary metabolites, i.e., that relate the occurrence of the floridosides with terpenes, and of digeneaside with bromate phenols, are a constant in these macro algae. V. obtusiloba falls into the latter case.
 
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Publishing Date
2024-06-13
 
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