DIHYDROCUCURBITACIN B: SEMISYNTHESIS OF NEW GLICOSIDE DERIVATIVES | Zendy

Vanessa Rocha Machado | Zendy; Karen Luise Lang | Zendy; Fernando Durán | Zendy; Gabriela M. Cabrera | Zendy; Jorge A. Palermo | Zendy; Eloir Paulo Schenkel | Zendy; Lílian Sibelle Campos Bernardes | Zendy

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DIHYDROCUCURBITACIN B: SEMISYNTHESIS OF NEW GLICOSIDE DERIVATIVES

Author(s) -

Vanessa Rocha Machado,

Karen Luise Lang,

Fernando Durán,

Gabriela M. Cabrera,

Jorge A. Palermo,

Eloir Paulo Schenkel,

Lílian Sibelle Campos Bernardes

Publication year - 2014

Publication title -

química nova

Language(s) - Spanish

Resource type - Journals

SCImago Journal Rank - 0.214

H-Index - 73

eISSN - 1678-7064

pISSN - 0100-4042

DOI - 10.5935/0100-4042.20140291

Subject(s) - semisynthesis , chemistry , computational biology , stereochemistry , biology

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. 2015, Sociedade Brasileira de Quimica. All rights reserved.Fil: Machado, Vanessa R.. Universidade Federal Da Santa Catarina; BrasilFil: Lang, Karen L.. Universidade Federal de Juiz de Fora;Fil: Duran, Fernando Javier. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanalisis y Metodos Fisicos En Química Organica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanalisis y Metodos Fisicos En Química Organica; ArgentinaFil: Cabrera, Gabriela Myriam. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanalisis y Metodos Fisicos En Química Organica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanalisis y Metodos Fisicos En Química Organica; ArgentinaFil: Palermo, Jorge Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanalisis y Metodos Fisicos En Química Organica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanalisis y Metodos Fisicos En Química Organica; ArgentinaFil: Schenkel, Eloir P.. Universidade Federal Da Santa Catarina; BrasilFil: Bernardes, Lílian S. C.. Universidade Federal Da Santa Catarina; Brasi

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