New flavonoid glycosides conjugates: synthesis, characterization, and evaluation of their cytotoxic activities

Authors

SAWSSEN SOUIEI
FATIMA BOUSEJRA-EL GARAH
MOHAMED AMINE BELKACEM
MANSOUR ZNATI
JALLOUL BOUAJILA
HICHEM BEN JANNET

Abstract

A series of novel halogenated 3-hydroxyflavones (3HFs) were prepared by reacting halogenated hydroxyacetophenones with the appropriate aromatic aldehyde. Glycosylation of 3HFs with acetobromoglucose and deprotection of the acetyl protective groups afforded the desired 3-$O$-flavonoids glycosides in satisfactory yields. All the prepared compounds were tested for their cytotoxic activity against HCT-116, MCF-7, and OVCAR-3 human cancer cell lines. The 3HFs exhibited higher cytotoxic activities compared with the glycosylated flavonoids. Overall, the structure-activity relationship study showed that the introduction of glycoside moiety at the C-3 OH position does not improve the bioactivity.

DOI

10.3906/kim-1807-88

Keywords

Halogenated 3-hydroxyflavones, glycosylation, cytotoxic activity

First Page

404

Last Page

414

Recommended Citation

SOUIEI, SAWSSEN; GARAH, FATIMA BOUSEJRA-EL; BELKACEM, MOHAMED AMINE; ZNATI, MANSOUR; BOUAJILA, JALLOUL; and JANNET, HICHEM BEN (2019) "New flavonoid glycosides conjugates: synthesis, characterization, and evaluation of their cytotoxic activities," Turkish Journal of Chemistry: Vol. 43: No. 2, Article 3. https://doi.org/10.3906/kim-1807-88
Available at: https://journals.tubitak.gov.tr/chem/vol43/iss2/3