Free-radical-scavenging effect of carbazole derivatives on DPPH and ABTS radicals

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作者
Tang, You-Zhi [1 ]
Liu, Zai-Qun [1 ]
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[1] Department of Organic Chemistry, College of Chemistry, Jilin University, No. 2519 Jiefang Road, Changchun 130021, China
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The major objective was to measure the trolox (6-hydroxy-2,5,7,8- tetramethylchroman-2-carboxylic acid) equivalent antioxidant capacity (TEAC) of carbazole derivatives (Ar2NHs) by means of scavenging 2,2'-diphenyl-1-picrylhydrazyl (DPPH) and the 2,2'-azinobis(3- ethylbenzothiazoline-6-sulfonate) radical cation (ABTS+&bull). The Ar2NHs included phenoxazine (PozNH), phenothiazine (PtzNH), iminostilbene (IsbNH) and diphenylamine (DpaNH), and the TEAC of trolox, α-tocopherol (TocH), l-ascorbic acid (VC) and l-ascorbyl-6-laurate (VC-12) were measured as well. The TEAC results revealed that the ability to scavenge DPPH (PozNH > IsbNH ~PtzNH ~TroH ~TocH ~VC ~VC12), differed from the ability to scavenge ABTS+ (PtzNH > IsbNH > PozNH > DpaNH ~TroH ~TocH ~VC ~VC12). CazNH did not react with DPPH and ABTS+&bull. Furthermore, the addition of acetic acid accelerated the reaction rate of Ar2NH to scavenge DPPH, suggesting that a sequential proton loss electron transfer (SPLET) mechanism occurred with amine-type antioxidants during the trapping of DPPH. In contrast, the addition of acetic acid or pyridine reduced the reaction rate of Ar2NH to scavenge ABTS+., suggesting that the hydrogen atom transfer (HAT) mechanism is the basis for the reaction that is occurring.[Figure not available: see fulltext.] © 2007 AOCS;
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