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1.
Antioxidants (Basel) ; 13(6)2024 Jun 20.
Article in English | MEDLINE | ID: mdl-38929184

ABSTRACT

Selenosugars are gaining growing interest due to their antioxidant efficacy, and their ability to inhibit glycosidases, repair skin tissue or reduce endothelial dysfunction. Among selenosugars, those in which selenium replaces heterocyclic oxygen in a 5-membered sugar were our focus, and their coupling with phenolic compounds appears to be a strategy aimed at producing new compounds with enhanced antioxidant efficacy. In this context, the Mitsunobu reaction has been advantageously explored to obtain trans-p-coumaroyl-1,4-deoxy-2,3-O-isopropylidene-4-seleno-d-ribose, trans-caffeoyl-1,4-deoxy-2,3-O-isopropylidene-4-seleno-d-ribose, and trans-feruloyl-1,4-deoxy-2,3-O-isopropylidene-4-seleno-d-ribose. These compounds underwent removal of the iso-propylidene group, to provide the corresponding hydroxycinnamoyl-1,4-deoxy-4-seleno-d-ribose. All compounds were characterized by Nuclear Magnetic Resonance (NMR) spectroscopy and High-Resolution Mass Spectrometry (HRMS). This latter technique was pivotal for ensuing cellular metabolomics analyses. In fact, after evaluating the anti-radical efficacy through 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) methods, which underline the massive role of the phenolic moiety in establishing efficacy, the compounds, whose cytotoxicity was first screened in two highly oxidative-stress-sensitive cells, were tested for their wound healing properties towards human HaCaT keratinocytes cells. Caffeoyl- and feruloyl selenosugars exerted a dose-dependent repair activity, while, as highlighted by the metabolomic approach, they were poorly taken up within the cells.

2.
Molecules ; 28(8)2023 Apr 15.
Article in English | MEDLINE | ID: mdl-37110721

ABSTRACT

Organic-inorganic hybrid materials were synthesized by a sol-gel route, using silicon alkoxide together with low molecular weight polycaprolactone and caffetannic acid. The synthesized hybrids were characterized by scanning Fourier-transform infrared (FTIR) spectroscopy, and their surface morphology was acquired by scanning electron microscopy (SEM) analysis. The hybrids were investigated for their antiradical capacity using the DPPH and ABTS tests, while the Kirby-Bauer test was used to evaluate their effects on the growth of Escherichia coli and Enterococcus faecalis. Furthermore, a biologically active hydroxyapatite layer has been observed to form on the surface of intelligently synthesized materials. The MTT direct test showed that the hybrid materials are biocompatible with NIH-3T3 fibroblast cells, while they were cytotoxic towards colon, prostate, and brain tumor cell lines. These results shed new light on the suitability of the synthesized hybrids in the medical field, thus affording knowledge on the features of the bioactive silica-polycaprolactone-chlorogenic acid hybrids.


Subject(s)
Chlorogenic Acid , Silicon Dioxide , Silicon Dioxide/chemistry , Chlorogenic Acid/chemistry , Durapatite/chemistry , Spectroscopy, Fourier Transform Infrared , Microscopy, Electron, Scanning , Anti-Bacterial Agents/pharmacology , Biocompatible Materials/chemistry
3.
Molecules ; 27(22)2022 Nov 10.
Article in English | MEDLINE | ID: mdl-36431852

ABSTRACT

There is growing interest in specialized metabolites for fortification strategies in feed and/or as an antioxidant, anti-inflammatory and antimicrobial alternative for the containment of disorders/pathologies that can also badly impact human nutrition. In this context, the improvement of the diet of ruminant species with polyphenols and the influence of these compounds on animal performance, biohydrogenation processes, methanogenesis, and quality and quantity of milk have been extensively investigated through in vitro and in vivo studies. Often conflicting results emerge from a review of the literature of recent years. However, the data suggest pursuing a deepening of the role of phenols and polyphenols in ruminant feeding, paying greater attention to the chemistry of the single compound or to that of the mixture of compounds more commonly used for investigative purposes.


Subject(s)
Livestock , Polyphenols , Animals , Humans , Animal Husbandry/methods , Ruminants , Animal Feed/analysis
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