Synthesis and Bioactivity Profile of 5-S-Lipoylhydroxytyrosol-Based Multidefense Antioxidants with a Sizeable (Poly)sulfide Chain
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- 作者：Lucia Panzella ; Luisella Verotta ; Luis Goya ; Sonia Ramos ; Mar铆a Angeles Mart铆n ; Laura Bravo ; Alessandra Napolitano ; Marco d鈥橧schia
- 刊名：Journal of Agricultural and Food Chemistry
- 出版年：2013
- 出版时间：February 27, 2013
- 年：2013
- 卷：61
- 期：8
- 页码：1710-1717
- 全文大小：343K
- 年卷期：v.61,no.8(February 27, 2013)
- ISSN：1520-5118
文摘
Novel 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鈥?b>4 were more efficient in the DPPH reduction assay (88鈥?3% reduction vs 68% by Trolox). At 10 渭M concentration, all compounds 1鈥?b>4 proved to be efficient hydroxyl radical scavengers (56鈥?9% inhibition) in a Fenton reaction assay. When administered to human HepG2 cells, 1鈥?b>4 proved to be nontoxic and exhibited marked protective effects against reactive oxygen species (ROS) generation (60鈥?4% inhibition at 1 渭M concentration) and cell damage induced by 400 渭M tert-butylhydroperoxide. All compounds 1鈥?b>4 exhibited overall greater antioxidant activity than hydroxytyrosol.