Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/36693
Type: Artigo de periódico
Title: Chemical constituents isolated from the bark of Guatteria blepharophylla (Annonaceae) and their antiproliferative and antimicrobial activities
Author: Costa, Emmanoel V.
Marques, Francisco de Assis
Pinheiro, Maria Lúcia B.
Braga, Raquel M.
Delarmelina, Camila
Duarte, Marta Cristina T.
Ruiz, Ana Lúcia T. G.
Carvalho, João Ernesto de
Maia, Beatriz H. L. N. S.
Abstract: Phytochemical study of the bark of Guatteria blepharophylla (Mart.) Mart. afforded twelve compounds, namely two sesquiterpenes, caryophyllene oxide (1) and spathulenol (3), one xanthone, lichexanthone (2), a mixture of steroids, β-sitosterol (4), and stigmasterol (5), and seven isoquinoline alkaloids, O-methylmoschatoline (6), lysicamine (7), nornuciferine (8), liriodenine (9), isocoreximine (10), subsessiline (11), and isomoschatoline (12). Their structures were established on the basis of spectroscopic methods. Compounds 1-6, 11 and 12 were reported for the first time in this species. The 13C NMR (nuclear magnetic resonance) data for the compounds 11 and 12 are described for the first time in the literature. The antiproliferative activity against human tumour cell lines and antimicrobial activities were investigated for the major compounds. Compound 9 showed significant activity against cell lines of breast (MCF-7, Michigan Cancer Foundation-7), superior to the positive control doxorubicin. Compound 12 presented antifungal activity similar to the positive control nystatin against Candida albicans.
O estudo fitoquímico das cascas de Guatteria blepharophylla (Mart.) Mart. forneceu 12 compostos, sendo dois sesquiterpenos, óxido de cariofileno (1) e espatulenol (3), uma xantona, liquexantona (2), uma mistura de esteróides, β-sitosterol (4) e estigmasterol (5), e sete alcalóides isoquinolínicos, O-metilmoschatolina (6), lysicamina (7), nornuciferina (8), liriodenina (9), isocoreximina (10), subsessilina (11) e isomoschatolina (12). Suas estruturas foram determinadas através de métodos espectroscópicos. Os compostos 1-6, 11 e 12 são reportados pela primeira vez nesta espécie. Os dados de RMN 13C (ressonância magnética nuclear) para os compostos 11 e 12 são descritos pela primeira vez na literatura. As atividades antiproliferativa em linhagens de células tumorais humanas e antimicrobiana foram investigadas para os compostos majoritários. O composto 9 mostrou significativa atividade contra linhagens de células de mama (MCF-7, Michigan Cancer Foundation-7), superior ao controle positivo doxorrubicina. O composto 12 apresentou atividade antifúngica similar ao controle positivo nistatina contra Candida albicans
Subject: Guatteria blepharophylla
antifungal and antiproliferative activities
alkaloids
terpenes
xanthone
Editor: Sociedade Brasileira de Química
Rights: aberto
Identifier DOI: 10.1590/S0103-50532011000600016
Address: http://dx.doi.org/10.1590/S0103-50532011000600016
http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532011000600016
Date Issue: 1-Jun-2011
Appears in Collections:Unicamp - Artigos e Outros Documentos

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