UMYMFOR   05516
UNIDAD DE MICROANALISIS Y METODOS FISICOS EN QUIMICA ORGANICA
Unidad Ejecutora - UE
artículos
Título:
Di-hidrocucurbitacina B: síntese de novos derivados glicosilados
Autor/es:
VANESSA R. MACHADO; KAREN L. LANG; FERNANDO J. DURÁN; GABRIELA M. CABRERA; JORGE A. PALERMO; ELOIR P. SCHENKEL; LÍLIAN S. C. BERNARDES
Revista:
QUÃMICA NOVA
Editorial:
SOC BRASILEIRA QUIMICA
Referencias:
Lugar: San Pablo; Año: 2015
ISSN:
0100-4042
Resumen:
DIHYDROCUCURBITACIN B: SEMISYNTHESIS OF NEW GLICOSIDE DERIVATIVES. 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 b-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.