Antioxidant generation and regeneration in lipid bilayers: the amazing case of lipophilic thiosulfinates and hydrophilic thiols.
We demonstrate that the garlic-derived chemopreventive agent allicin and the related anamu-derived petivericin are poor radical-trapping antioxidants in lipid bilayers, but that the in situ reaction of a lipophilic analog and a hydrophilic thiol yields an extremely potent radical-trapping antioxidant that can be recycled in the presence of excess thiol.
Department of Chemistry, University of Ottawa, 10 Marie Curie Pvt., Ottawa, Ontario, Canada.
Feng
F
Zheng
Derek A
DA
Pratt
D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D008051:Lipid Bilayers / Q000737:chemistry*; D015394:Molecular Structure; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013441:Sulfinic Acids / Q000737:chemistry*
D000975:Antioxidants; D008051:Lipid Bilayers; D013438:Sulfhydryl Compounds; D013441:Sulfinic Acids; C100040:thiosulfinic acids