208
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

The role of sulfur and heavier chalcogens in the chemistry of antioxidants

, &
Pages 638-642 | Received 28 Mar 2019, Accepted 29 Mar 2019, Published online: 19 Apr 2019

References

  • Amorati, R.; Valgimigli, L. Advantages and Limitations of Common Testing Methods for Antioxidants. Free Radic. Res. 2015, 49, 633–649. DOI:10.3109/10715762.2014.996146.
  • Amorati, R.; Valgimigli, L. Methods to Measure the Antioxidant Activity of Phytochemicals and Plant Extracts. J. Agric. Food Chem. 2018, 4, 3324–3329. DOI:10.1021/acs.jafc.8b01079.
  • Baschieri, A.; Daci Ajvazi, M.; Folifack Tonfack, J. L.; Valgimigli, L.; Amorati, R. Explaining the Antioxidant Activity of Some Common Non-Phenolic Components of Essential Oils. Food. Chem. 2017, 232, 656–663. DOI:10.1016/j.foodchem.2017.04.036.
  • Burton, G. W.; Doba, T.; Gabe, E. J.; Hughes, L.; Lee, F. L.; Prasad, L.; Ingold, K. U. Autoxidation of Biological Molecules. 4. Maximizing the Antioxidant Activity of Phenols. J. Am. Chem. Soc. 1985, 107, 7053–7065. DOI:10.1021/ja00310a049.
  • Vaidya, V.; Ingold, K. U.; Pratt, D. A. Garlic: Source of the Ultimate Antioxidants-Sulfenic Acids. Angew. Chem. Int. Ed. 2009, 48, 157–160. DOI:10.1002/anie.200804560.
  • Roos, G.; Messens, J. Protein Sulfenic Acid Formation: From Cellular Damage to Redox Regulation. Free Radic. Biol. Med. 2011, 51, 314–326. 10.1016/j.freeradbiomed.2011.04.031
  • Block, E. Garlic and Other Alliums: The Lore and the Science; RSC Press: Cambridge, 2009.
  • McGrath, A. J.; Garrett, G. F.; Valgimigli, L.; Pratt, D. A. The Redox Chemistry of Sulfenic Aicds. J. Am. Chem. Soc. 2010, 132, 16759. DOI:10.1021/ja1083046.
  • Amorati, R.; Pedulli, G. F. Do Garlic-Derived Allyl Sulfides Scavenge Peroxyl Radicals? Org. Biomol. Chem. 2008, 6, 1103. DOI:10.1039/b719348c.
  • Lucarini, M.; Pedulli, G. F.; Valgimigli, L.; Amorati, R.; Minisci, F. Thermochemical and Kinetic Studies of a Bisphenol Antioxidant. J. Org. Chem. 2001, 66, 5456–5462.
  • Amorati, R.; Pedulli, G. F.; Valgimigli, L. Kinetic and Thermodynamic Aspects of the Chain-Breaking Antioxidant Activity of Ascorbic Acid Derivatives in Non-Aqueous Media. Org. Biomol. Chem. 2011, 9, 3792–3800. DOI:10.1039/c1ob05334e.
  • Amorati, R.; Lynett, P. T.; Valgimigli, L.; Pratt, D. A. The Reaction of Sulfenic Acids with Peroxyl Radicals: Insights into the Radical-Trapping Antioxidant Activity of Plant-Derived Thiosulfinates. Chem. Eur. J. 2012, 18, 6370–6379. DOI:10.1002/chem.201103459.
  • Stadtman, T. C. Biosynthesis and Function of Selenocysteine-Containing Enzymes. J. Biol. Chem. 1991, 266, 16257–16260.
  • Goto, K.; Nagahama, M.; Mizushima, T.; Shimada, K.; Kawashima, T.; Okazaki, R. The First Direct Oxidative Conversion of a Selenol to a Stable Selenenic Acid: Experimentral Demonstration of Three Processes Included in the Catalytic Cycle of Glutathione Peroxidase. Org. Lett. 2001, 3, 3569–3572. DOI:10.1021/ol016682s.
  • Mugesh, G.; Du Mont, W. W.; Sies, H. Chemistry of Biologically Important Synthetic Organoselenium Compounds. Chem. Rev. 2001, 101, 2125–2179. DOI:10.1021/cr000426w.
  • Ishii, A.; Matsubayashi, S.; Takahashi, T.; Nakayama, J. Preparation of a Selenenic Acid and Isolation of Selenoseleninates. J. Org. Chem. 1999, 64, 1084–1085. DOI:10.1021/jo982039g.
  • Zielinski, Z.; Presseau, N.; Amorati, R.; Valgimigli, L.; Pratt, D. A. Redox Chemistry of Selenenic Acids and the Insight It Brings on Transition State Geometry in the Reactions of Peroxyl Radicals. J. Am. Chem. Soc. 2014, 136, 1570–1578. DOI:10.1021/ja411493t.
  • Valgimigli, L.; Pratt, D. A. Antioxidants in Chemistry and Biology. In Encyclopedia of Radicals in Chemistry, Biology and Materials; Chatgilialoglu, C.; Studer, A. Eds.; Wiley: Chichester, 2012; pp. 1623–1677.
  • Zahalka, H. A.; Robillard, B.; Hughes, L.; Lusztyk, J.; Burton, G. W.; Janzen, E. G.; Kotake, Y.; Ingold, K. U. Antioxidant Activity of 1-Thio-.Alpha.-Tocopherol and Related Compounds. EPR, ENDOR, and UV-Visible Absorption Spectra of Some of the Derived Phenoxyl Radicals. J. Org. Chem. 1988, 53, 3739–3745.
  • Shanks, D.; Amorati, R.; Fumo, M. G.; Pedulli, G. F.; Valgimigli, L.; Engman, L. Synthesis and Antioxidant Profile of all-rac-alpha-selenotocopherol. J. Org. Chem. 2006, 71, 1033–1038. DOI:10.1021/jo052133e.
  • Amorati, R.; Pedulli, G. F.; Valgimigli, L.; Johansson, H.; Engman, L. Organochalcogen Substituents in Phenolic Antioxidants. Org. Lett. 2010, 12, 2326–2329. DOI:10.1021/ol100683u.
  • Amorati, R.; Catarzi, F.; Menichetti, S.; Pedulli, G. F.; Viglianisi, C. Effect of Ortho-SR Groups on O-H Bond Strength and H-atom Donating Ability of Phenols: A Possible Role for the Tyr-Cys Link in Galactose Oxidase active Site? J. Am. Chem. Soc. 2008, 130, 237–244. DOI:10.1021/ja075554h.
  • Kumar, S.; Johansson, H.; Engman, L.; Valgimigli, L.; Amorati, R.; Fumo, M. G.; Pedulli, G. F. Regenerable Chain-Breaking 2,3-dihydrobenzo[b]selenophene-5-ol Antioxidants. J. Org. Chem. 2007, 72, 2583–2595. DOI:10.1021/jo0700023.
  • Johansson, H.; Shanks, D.; Engman, L.; Amorati, R.; Pedulli, G. F.; Valgimigli, L. Long-Lasting Antioxidant Protection: A Regenerable BHA Analogue. J. Org. Chem. 2010, 75, 7535–7541. DOI:10.1021/jo101239c.
  • Amorati, R.; Valgimigli, L.; Dinér, P.; Bakhtiari, K.; Saeedi, M.; Engman, L. Multi-Faceted Reactivity of Alkyltellurophenols towards Peroxyl Radicals: Catalytic Antioxidant Versus Thiol-Depletion Effect. Chem. Eur. J. 2013, 19, 7510–7522. DOI:10.1002/chem.201300451.
  • Jamier, V.; Ba, L. A.; Jacob, C. Selenium- and Tellurium-Containing Multifunctional Redox Agents as Biochemical Redox Modulators with Selective Cytotoxicity. Chem. Eur. J. 2010, 16, 10920–10928. DOI:10.1002/chem.201000884.
  • Chauvin, J. R.; Haidasz, E. A.; Griesser, M.; Pratt, D. A. Polysulfide-1-Oxides React with Peroxyl Radicals as Quickly as Hindered Phenolic Antioxidants and Do so by a Surprising Concerted Homolytic Substitution. Chem. Sci. 2016, 7, 6347–6356. DOI:10.1039/c6sc014.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.