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

Química Nova

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】

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