DI-HIDROCUCURBITACINA B: SEMI-SÍNTESE DE NOVOS DERIVADOS GLICOSILADOS

• Autor(a) principal: Machado,Vanessa R.
• Data de Publicação: 2015
• Outros Autores: Lang,Karen L., Durán,Fernando J., Cabrera,Gabriela M., Palermo,Jorge A., Schenkel,Eloir P., Bernardes,Lílian S. C.
• Tipo de documento: Artigo
• Idioma: por
• Título da fonte: Química Nova (Online)
• Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422015000100037
• topic: Wilbrandia ebracteata; glycosylated cucurbitacins; O-glycosylation reaction; molecular modification

In the last ten years, the interest in natural and semi-synthetic cucurbitacin derivatives has increased, primarily due their cytotoxic and anti-tumoral activities. However, the isolation of glycosylated cucurbitacins has been difficult due the presence of β-glucosidase enzyme. With the aim of obtaining new glycosylated derivatives, the glycosylation of dihydrocucurbitacin B under Köenigs-Knorr and imidate reaction conditions was studied. Novel glycoside derivatives 16-(1,2-orthoacetate-3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-dihydrocucurbitacin B (2), 2-O-β-D-2,3,4,6-tetra-O-acetyl-galactopyranosyl dihydrocucurbitacin B (3) and 2-O-β-D-galactopyranosyl dihydrocucurbitacin B (4) were synthesized for the first time in 17% (2 and 3) and 48% (4) yields.