Innovative Cosmeceutical Ingredients: Harnessing Selenosugar-Linked Hydroxycinnamic Acids for Antioxidant and Wound-Healing Properties

• Published in: Antioxidants 2024-06, Vol.13 (6), p.744
• Main Authors: Cimmino, Giovanna, De Nisco, Mauro, Piccolella, Simona, Gravina, Claudia, Pedatella, Silvana, Pacifico, Severina
• Format: Article
• Language: English
• Subjects: 2,2-diphenyl-1-picrylhydrazyl; Acids; anti-radical activity; antioxidant activity; Antioxidants; Chromatography; cosmetics; Cytotoxicity; D-Ribose; dose response; Fourier transforms; glycosidases; heterocyclic compounds; humans; hydro-cinnamic acids; Keratinocytes; mass spectrometry; Mass spectroscopy; Metabolomics; moieties; NMR; Nuclear magnetic resonance; nuclear magnetic resonance spectroscopy; oxygen; Phenolic compounds; Ribose; Selenium; selenosugars; Skin; Software; Solvents; Sugar; sugars; Sulfonic acid; UHPLC–HRMS; Wound healing
• ISSN: 2076-3921; 2076-3921
• DOI: 10.3390/antiox13060744

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 - -coumaroyl-1,4-deoxy-2,3- -isopropylidene-4-seleno-d-ribose, -caffeoyl-1,4-deoxy-2,3- -isopropylidene-4-seleno-d-ribose, and -feruloyl-1,4-deoxy-2,3- -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.