ICCAS OpenIR
Radical dynamics of puerarin as revealed by laser flash photolysis and spin density analysis
Tian, Yu-Xi1,2; Han, Rui-Min1; Fu, Li-Min1; Zhang, Jian-Ping1,2; Skibsted, Leif H.3
2008-02-21
Source PublicationJOURNAL OF PHYSICAL CHEMISTRY B
ISSN1520-6106
Volume112Issue:7Pages:2273-2280
AbstractPuerarin, a C-glycoside of daidzein, forms upon direct photoexcitation in acetonitrile an excited-state with a lifetime of 4.2 mu s assigned by oxygen quenching and sensitized formation of triplet zeaxanthin as a triplet and phenoxyl radicals of ms lifetime insensitive to oxygen and with spin density delocalized over the ACB isoflavonoid ring system, [ACB](center dot), as shown by laser flash photolysis and theoretical spin density calculations. Photoexcitation of A-ring 7-phenolate puerarin yields a [AC](center dot) radical, which converts into the [ACB](center dot) radical with a rate constant of 3.6 x 10(5) s(-1) in 5% methanolic acetonitrile in a process triggered by B-ring deprotonation (4'-phenol). For the 7-phenolate with the 4'-phenol derivatized to yield a propyl anisole, no rearrangement of the initially formed [AC](center dot) radical was observed. With the A-ring phenol derivatized, the 7-propyl-4'-phenolate forms a radical with spin density delocalized over the CB ring system, [CB](center dot), together with a minor fraction of [ACB](center dot) due to propyl radical dissociations confirmed by BDE-calculations. Dianionic puerarin forms initially the [ACB](center dot) radical, which is converted into the [CB](center dot) radical in a slower process (1.6 x 10(4) s(-1)) assigned to 7-methylation. The radical dynamics is discussed in relation to puerarin/carotenoid antioxidant synergism at water/lipid interphases.
DOI10.1021/jp709579s
Indexed BySCI
Language英语
WOS IDWOS:000253222300050
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:10[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/63346
Collection中国科学院化学研究所
Corresponding AuthorHan, Rui-Min
Affiliation1.Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China
2.Chinese Acad Sci, Inst Chem, State Key Lab Struct Chem Unstabe & Stable Specie, BNLMS, Beijing 100080, Peoples R China
3.Univ Copenhagen, Fac Life Sci, Dept Food Chem, DK-1058 Frederiksberg, Denmark
Recommended Citation
GB/T 7714
Tian, Yu-Xi,Han, Rui-Min,Fu, Li-Min,et al. Radical dynamics of puerarin as revealed by laser flash photolysis and spin density analysis[J]. JOURNAL OF PHYSICAL CHEMISTRY B,2008,112(7):2273-2280.
APA Tian, Yu-Xi,Han, Rui-Min,Fu, Li-Min,Zhang, Jian-Ping,&Skibsted, Leif H..(2008).Radical dynamics of puerarin as revealed by laser flash photolysis and spin density analysis.JOURNAL OF PHYSICAL CHEMISTRY B,112(7),2273-2280.
MLA Tian, Yu-Xi,et al."Radical dynamics of puerarin as revealed by laser flash photolysis and spin density analysis".JOURNAL OF PHYSICAL CHEMISTRY B 112.7(2008):2273-2280.
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