Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/40439
Type: Artigo de periódico
Title: Aporphine and tetrahydroprotoberberine alkaloids from the leaves of Guatteria friesiana (Annonaceae) and their cytotoxic activities
Author: Costa, Emmanoel Vilaça
Cruz, Pedro Ernesto O. da
Pinheiro, Maria Lúcia B.
Marques, Francisco A.
Ruiz, Ana Lúcia T. G.
Marchetti, Gabriela M.
Carvalho, João Ernesto de
Barison, Andersson
Maia, Beatriz Helena L. N. S.
Abstract: Phytochemical investigation of the leaves of Guatteria friesiana (Annonaceae) afforded three new isoquinoline alkaloids, 13-hydroxy-discretinine, 6,6a-dehydroguatteriopsiscine and 9-dehydroxy-1-methoxy-dihydroguattouregidine. Eight known alkaloids were also isolated, 13-hydroxy-2,3,9,10-tetramethoxyprotoberberine, guatteriopsiscine, lysicamine, liriodenine, atherospermidine, lanuginosine, 7,8-dihydro-8-hydroxypalmatine and palmatine. 13-Hydroxy-2,3,9,10-tetramethoxyprotoberberine was only obtained by synthesis and is being reported as a natural product for the first time. The structures of the isolated alkaloids were established by extensive analysis of 1D and 2D nuclear magnetic resonance (NMR) and mass spectrometric (MS) data, as well as by comparison with data reported in the literature. The in vitro cytotoxic activity of the major alkaloids was evaluated against tumor and non-tumor cell lines. All of the alkaloids evaluated were determined to be inactive based on National Cancer Institute (NCI/USA) criteria. However, the alkaloid palmatine exhibited a cytostatic effect on MCF-7 (breast) and U251 (glioma) human tumor cell lines, with GI50 values lower than 20.0 µmol L-1 (10.5 and 16.2 µmol L-1, respectively), suggesting a selective cytotoxic action.
A investigação fitoquímica das folhas de Guatteria friesiana (Annonaceae) levou à obtenção de três novos alcaloides isoquinolínicos, 13-hidroxi-discretinina, 6,6a-desidroguateriopsiscina e 9-desidroxi-1-metoxi-diidroguattouregidina, juntamente com oito alcaloides conhecidos, 13-hidroxi-2,3,9,10-tetrametoxiprotoberberina, guateriopsiscina, lisicamina, liriodenina, aterospermidina, lanuginosina, 7,8-diidro-8-hidroxipalmatina e palmatina. 13-Hidroxi-2,3,9,10-tetrametoxiprotoberberina, obtido somente através de síntese, é relatada pela primeira vez como produto natural. As estruturas dos alcaloides isolados foram elucidadas por extensivas análises de ressonância magnética nuclear (RMN 1D e 2D), espectrometria de massas (MS) e comparação com os dados descritos na literatura. A atividade citotóxica in vitro dos alcaloides majoritários foi avaliada frente a linhagens de células tumorais e não tumorais. Considerando a atividade média, de acordo com os critérios do National Cancer Institute (NCI/EUA), todos os alcaloides avaliados foram inativos. Entretanto, o alcaloide palmatina apresentou efeito citostático para as linhagens MCF-7 (mama) e U251 (glioma) com valores de GI50 abaixo de 20,0 µmol L-1 (10,5 e 16,2 µmol L-1, respectivamente), sugerindo uma ação citotóxica seletiva.
Subject: Guatteria friesiana
aporphine alkaloids
tetrahydroprotoberberine alkaloids
cytotoxic activity
Editor: Sociedade Brasileira de Química
Rights: aberto
Identifier DOI: 10.5935/0103-5053.20130103
Address: http://dx.doi.org/10.5935/0103-5053.20130103
http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013000500011
Date Issue: 1-May-2013
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

Files in This Item:
File Description SizeFormat 
S0103-50532013000500011.pdf1.41 MBAdobe PDFView/Open


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.