Role of Allyl Group in the Hydroxyl and Peroxyl Radical Scavenging Activity of S-Allylcysteine

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• 作者：Perla D. Maldonado ; J. Ra煤l Alvarez-Idaboy ; Adriana Aguilar-Gonz谩lez ; Alfonso Lira-Rocha ; Helgi Jung-Cook ; Omar Noel Medina-Campos ; Jos茅 Pedraza-Chaverr铆 ; Annia Galano
• 刊名：Journal of Physical Chemistry B
• 出版年：2011
• 出版时间：November 17, 2011
• 年：2011
• 卷：115
• 期：45
• 页码：13408-13417
• 全文大小：1006K
• 年卷期：v.115,no.45(November 17, 2011)
• ISSN：1520-5207

文摘

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 (^{鈥?/sup>OH), although its potential ability to scavenge peroxyl radical (ROO鈥?/sup>) has not been explored. In this work the ability of SAC to scavenge ROO鈥?/sup> was evaluated, as well as the role of the allyl group (鈥擲鈥擟H₂鈥擟H鈺怌H₂) in its free radical scavenging activity. Two derived compounds of SAC were prepared: S-benzylcysteine (SBC) and S-propylcysteine (SPC). Their abilities to scavenge 鈥?/sup>OH and ROO鈥?/sup> were measured. A computational analysis was performed to elucidate the mechanism by which these compounds scavenge 鈥?/sup>OH and ROO鈥?/sup>. SAC was able to scavenge 鈥?/sup>OH and ROO鈥?/sup>, 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鈥?/sup>.}