Química Nova | |
DI-HIDROCUCURBITACINA B: SEMI-SÍNTESE DE NOVOS DERIVADOS GLICOSILADOS | |
Vanessa R. Machado1  Karen L. Lang1  Fernando J. Durán1  Gabriela M. Cabrera1  Jorge A. Palermo1  Eloir P. Schenkel1  Lílian S. C. Bernardes1  | |
关键词: Wilbrandia ebracteata; glycosylated cucurbitacins; O-glycosylation reaction; molecular modification; | |
DOI : 10.5935/0100-4042.20140291 | |
来源: SciELO | |
【 摘 要 】
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.
【 授权许可】
CC BY-NC
All the contents of this journal, except where otherwise noted, is licensed under a Creative Commons Attribution License
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