Seleno-glycoconjugates For Nutraceutical Application

Cells are steady subject to the action of reactive species (RS), both radical and non-radical, which can oxidize biological macromolecules (lipids, proteins, and nucleic acids) altering the membranes, inactivating enzymes, receptors and damaging the genome. [1] Oxidative stress, a disequilibrium redox state, is brought on by a higher concentration of pro-oxidant reactive species (RS) and, by contrast, a lower concentration of endogenous antioxidants in the body. Oxidative stress influences the onset of several diseases, including inflammatory bowel disease, cardiovascular disease, Alzheimer's disease, diabetes, and cancer. [2] This uncomfortable scenario can be solved by exogenous antioxidants, which could restore the redox balance. [3] Nutraceuticals and dietary phytochemicals may be used to lower oxidative stress and consequently to promote human’s health.[1] The regular consumption of foods such as red berries, chocolate, tea, wine, and fresh fruits is the main source of polyphenols in the human diet, which may have a health-promoting effect. However, the possibility use of polyphenols are severely limited by their low bioavailability and poor penetration into the cell membrane. [4] In the frame of the evaluation their real potential as a strategy against disease, it well know that glycosylation affect chemical, biological and physical properties of polyphenols allowing a better absorption in the small intestine [5] The goal of synthesizing organo-Se-compounds with (poly)phenols is to create new compounds that overcome the bioavailability barrier and have a synergistic antioxidant effect. The proposed method involves the D-ribose derivative synthesis to obtain the donor, which is then used to generate glycoconjugates containing the well-known (poly)phenols by a Mitsunobu reaction. [6] Herein, the biological activity of the hydroquinone glycoconjugate is presented in terms of its antioxidant capability, obtained by ABTS and DPPH methods, and cytotoxic activity. The latter was evaluated by MTT assay on Caco-2 intestinal epithelial cells, SHSY5Y neuroblastoma cells, and HaCaT keratinocytes. The glycoconjugate caused the greatest inhibition of dehydrogenases activity compared with selenosugar, exerting a dose- and time-dependent antiproliferative effects. The phenolic moiety seems to mainly influence cell proliferation, also showing a peculiar cell-dependent sensitivity.