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Doctoral Thesis
DOI
10.11606/T.46.1997.tde-12112015-153501
Document
Author
Full name
Fernanda Rodrigues Garcez
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 1997
Supervisor
Committee
Roque, Nidia Franca (President)
Emerenciano, Vicente de Paulo
Furlan, Maysa
Patitucci, Maria Lucia
Vieira, Paulo Cezar
Title in Portuguese
Limonóides e protolimonóides de Trichilia elegans ssp. Elegans A. Juss. (Meliaceae)
Keywords in Portuguese
Bioquímica Vegetal
Limonóides
Meliaceae
Produtos Naturais
Química Orgânica
Trichilia Elegans Ssp Elegans
Abstract in Portuguese
o presente trabalho teve como objetivo realizar o estudo químico das sementes de Trichilia elegans ssp. Elegans A. Juss. (coletadas no município de Corumbá, MS), visando o isolamento e identificação ou elucidação estrutural dos seus metabólitos secundários, particularmente limonóides. Da fase diclorometânica, obtida de uma partição efetuada com o extrato etanólico das sementes, foram isoladas, através de técnicas cromatográficas de separação (cromatografia em colunas de sílica gel, de Sephadex LH 20 e CLAE em fase reversa), dezoito substâncias, compreendendo: dois protolimonóides, onze limonóides com esqueleto do tipo obacunol (abertura dos anéis A e D), quatro com esqueleto do tipo ivorensato de metila (abertura dos anéis A, B e D) e 3β-O-β-D-glicopiranosilsitosterol. Todas as substâncias são inéditas, com exceção do esteróide glicosilado e de dois limonóides com esqueleto do tipo obacunol (kihadaninas A e B). As determinações estruturais foram efetuadas com base em dados espectroscópicos de RMN 1H e 13C, incluindo experimentos bidimensionais (COSY 1H-1H, COSY 1H-13C, HMQC, NOESY e HMBC); a partir de informações obtidas dos espectros de massas e na região do IV e através de dados de difração de raios-X. Quatro dos limonóides obtidos foram submetidos a um ensaio biológico de atividade antitumoral, utilizando-se linhagens mutantes de Saccharomyces cerevisiae, porém, mostraram-se inativos.
Title in English
Limonoids and protolimonoids of Trichilia elegans ssp. Elegans A. Juss. (Meliaceae)
Keywords in English
Biochemical Plant
Limonoids
Meliaceae
Natural Products
Organic chemistry
Trichilia elegans ssp. Elegans
Abstract in English
The present work describes the isolation and identification or structural elucidation of the chemical constituents of the seeds of Trichilia elegans ssp. Elegans A. Juss., collected in Corumbá, MS. From the dichloromethane solubles, obtained from partition of the ethanolic extract from the seeds, eighteen substances have been isolated, after a combination of column and flash chromatography on silica gel, gel filtration and reversed phase HPLC separations. The isolated substances have been characterized as two new protolimonoids, nine new obacunol- and four new methyl ivorensate-type limonoids, in addition to two known limonoids belonging to the obacunol group (kihadanins A and B) and 3-O-β-D-glucopyranosyl-sitosterol. The structures of these compounds have been established on the basis of 1D (1H, 13C) and 2D (1H-1H and 1H-13C COSY, HMQC, HMBC and NOESY) NMR spectroscopic techniques, IR and mass spectral data and X-ray crystallographic analyses. Four of the isolated limonoids have been tested against DNA reparr deficient mutants of Saccharomyces cerevisiae but, nevertheless, shown to be inactive.
 
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Publishing Date
2015-11-12
 
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