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Synthesis and bioactivity profile of 5-S-lipoylhydroxytyrosol-based multidefense antioxidants with a sizeable (poly)sulfide chain

AuthorsPanzella, Lucia; Verotta, L.; Goya, Luis ; Ramos, Sonia ; Martín, M. Ángeles ; Bravo, Laura ; Napolitano, Alessandra; D'Ischia, Marco
Issue Date2013
PublisherAmerican Chemical Society
CitationJournal of Agricultural and Food Chemistry 61(8): 1710-1717 (2013)
AbstractNovel polyfunctionalized antioxidants, 5-S-lipoylhydroxytyrosol (1) and its disulfide 2, trisulfide 3, and tetrasulfide 4, were prepared from tyrosol and dihydrolipoic acid in the presence, when appropriate, of sulfur. Compound 1 exhibited significant activity in the ferric reducing/antioxidant power (FRAP) assay (1.60 Trolox equiv), whereas polysulfides 2-4 were more efficient in the DPPH reduction assay (88-93% reduction vs 68% by Trolox). At 10 οM concentration, all compounds 1-4 proved to be efficient hydroxyl radical scavengers (56-69% inhibition) in a Fenton reaction assay. When administered to human HepG2 cells, 1-4 proved to be nontoxic and exhibited marked protective effects against reactive oxygen species (ROS) generation (60-84% inhibition at 1 οM concentration) and cell damage induced by 400 οM tert- butylhydroperoxide. All compounds 1-4 exhibited overall greater antioxidant activity than hydroxytyrosol. © 2012 American Chemical Society.
Identifiersdoi: 10.1021/jf302690c
issn: 0021-8561
Appears in Collections:(ICTAN) Artículos
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