Full metadata record
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Shunichi Fukuzumi | * |
dc.date.accessioned | 2016-08-28T10:08:46Z | - |
dc.date.available | 2016-08-28T10:08:46Z | - |
dc.date.issued | 2012 | * |
dc.identifier.issn | 0009-2673 | * |
dc.identifier.other | OAK-9224 | * |
dc.identifier.uri | https://dspace.ewha.ac.kr/handle/2015.oak/223015 | - |
dc.description.abstract | The kinetics for the reaction of the 2,2-diphenyl-1-picrylhydrazyl radical (DPPḢ) with artepillin C, a prenylated phenylpropanoid found specifically in Brazilian propolis, and its analogues was examined in deaerated acetonitrile (MeCN) to shed light on the mechanism for the radical-scavenging reaction of phenolic antioxidants as well as on the structureactivity relationship. Among the examined analogues, a compound having a catechol moiety is found to have the largest second-order rate constant (k) for the DPPḢ-scavenging reaction. The deuterium kinetic isotope effect of 1.6 was observed for the DPPḢ-scavenging reaction of artepillin C in the presence of 0.13M CD 3OD or CH 3OH in deaerated MeCN at 298 K. The log k values were found to be linearly correlated with calculated energy difference values (DHT, HT: hydrogen transfer) between the artepillin C analogues and the corresponding phenoxyl radicals, while such a linear correlation cannot be observed between the log k values and calculated ionization potentials (IP), DHT 1 IP, or experimental one-electron-oxidation potentials of the artepillin C analogues. These results together with a calculated structure of the transition state for the reaction between the artepillin C analogue and DPPḢ suggest that the DPPḢ- scavenging reaction of the artepillin C analogues in deaerated MeCN proceeds via a one-step hydrogen-atom transfer from the phenolic OH group to DPPḢ rather than an electron transfer followed by proton transfer. © 2012 The Chemical Society of Japan. | * |
dc.language | English | * |
dc.title | Kinetics and mechanism for the scavenging reaction of the 2,2-diphenyl-1-picrylhydrazyl radical by synthetic artepillin c analogues | * |
dc.type | Article | * |
dc.relation.issue | 8 | * |
dc.relation.volume | 85 | * |
dc.relation.index | SCI | * |
dc.relation.index | SCIE | * |
dc.relation.index | SCOPUS | * |
dc.relation.startpage | 877 | * |
dc.relation.lastpage | 883 | * |
dc.relation.journaltitle | Bulletin of the Chemical Society of Japan | * |
dc.identifier.doi | 10.1246/bcsj.20120005 | * |
dc.identifier.wosid | WOS:000308835100005 | * |
dc.identifier.scopusid | 2-s2.0-84865226235 | * |
dc.author.google | Kawashima T. | * |
dc.author.google | Manda S. | * |
dc.author.google | Uto Y. | * |
dc.author.google | Ohkubo K. | * |
dc.author.google | Hori H. | * |
dc.author.google | Matsumoto K.-I. | * |
dc.author.google | Fukuhara K. | * |
dc.author.google | Ikota N. | * |
dc.author.google | Fukuzumi S. | * |
dc.author.google | Ozawa T. | * |
dc.author.google | Anzai K. | * |
dc.author.google | Nakanishi I. | * |
dc.contributor.scopusid | Shunichi Fukuzumi(35430038100;58409757400) | * |
dc.date.modifydate | 20240802081000 | * |