Aporphine and Tetrahydroprotoberberine Alkaloids from the Leaves of Guatteria friesiana (Annonaceae) and their Cytotoxic Activities

作者：Costa Emmanoel Vilaca^*; da Cruz Pedro Ernesto O; Pinheiro Maria Lucia B; Marques Francisco A; Ruiz Ana Lucia T G; Marchetti Gabriela M; de Carvalho Joao Ernesto; Barison Andersson; Maia Beatriz Helena L N S

来源：Journal of the Brazilian Chemical Society, 2013, 24(5): 788-+.

DOI：10.5935/0103-5053.20130103

• Guatteria friesiana
• aporphine alkaloids
• tetrahydroprotoberberine alkaloids
• cytotoxic activity

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 GI(50) values lower than 20.0 mu mol L-1 (10.5 and 16.2 mu mol L-1, respectively), suggesting a selective cytotoxic action.

• 出版日期2013-5