DI-HIDROCUCURBITACINA B: SÍNTESE DE NOVOS DERIVADOS GLICOSILADOS

ROCHA MACHADO V.; LANG, K. L.; DURAN F. J.; CABRERA G. M.; PALERMO J. A.; SCHENKEL E. P.; BERNARDES L. S. C.

QUíMICA NOVA

SOC BRASILEIRA QUIMICA

Lugar: San Pablo; Año: 2015 vol. 38 p. 37 - 41

0100-4042

In the last ten years, the interest in natural and semi-synthetic cucurbitacins derivatives has increased mainly due their citotoxic and anti-tumoral activities. However, the isolation of glycosylate cucurbitacins has been difficult due the presence of -Glucosidase enzyme. With the aim of obtaining new glycosilated derivatives, the glycosylation of dihydrocucurbitacin B under Koenigs-Knorr and imidate reaction conditions was studied. Novel glycosides 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-galactopyranoside dihydrocucurbitacin B (3) and 2-O-β-D-galactopyranoside dihydrocucurbitacin B (4) were synthesized for the first time in 17% (2 and 3) and 48% (4) yields