title: Role of allyl group in the hydroxyl and peroxyl radical scavenging activity of S-allylcysteine.
abstract: S-Allylcysteine (SAC) is the most abundant compound in aged garlic extracts, and its antioxidant properties have been demonstrated. It is known that SAC is able to scavenge different reactive species including hydroxyl radical (•OH), although its potential ability to scavenge peroxyl radical (ROO•) has not been explored. In this work the ability of SAC to scavenge ROO• was evaluated, as well as the role of the allyl group (-S-CH(2)-CH═CH(2)) in its free radical scavenging activity. Two derived compounds of SAC were prepared: S-benzylcysteine (SBC) and S-propylcysteine (SPC). Their abilities to scavenge •OH and ROO• were measured. A computational analysis was performed to elucidate the mechanism by which these compounds scavenge •OH and ROO•. SAC was able to scavenge •OH and ROO•, in a concentration-dependent way. Such activity was significantly ameliorated when the allyl group was replaced by benzyl or propyl groups. It was shown for the first time that SAC is able to scavenge ROO•.
authors: Patología Vascular Cerebral, Instituto Nacional de Neurología y Neurocirugía Manuel Velasco Suárez, México DF, Mexico. maldonado.perla@gmail.com
authors: Perla D
authors: PD
authors: Maldonado
authors: J Raúl
authors: JR
authors: Alvarez-Idaboy
authors: Adriana
authors: A
authors: Aguilar-González
authors: Alfonso
authors: A
authors: Lira-Rocha
authors: Helgi
authors: H
authors: Jung-Cook
authors: Omar Noel
authors: ON
authors: Medina-Campos
authors: José
authors: J
authors: Pedraza-Chaverrí
authors: Annia
authors: A
authors: Galano
mesh_terms: D003545:Cysteine / Q000031:analogs & derivatives* / Q000737:chemistry; D016166:Free Radical Scavengers / Q000737:chemistry*; D017665:Hydroxyl Radical / Q000737:chemistry*; D010545:Peroxides / Q000737:chemistry*; D011789:Quantum Theory; D013816:Thermodynamics
chemical_list: D016166:Free Radical Scavengers; D010545:Peroxides; C049375:perhydroxyl radical; D017665:Hydroxyl Radical; C028742:S-propylcysteine; C065299:S-allylcysteine; C002206:S-benzylcysteine; D003545:Cysteine