ICCAS OpenIR
Daidzein as an Antioxidant of Lipid: Effects of the Microenvironment in Relation to Chemical Structure
Liang, Jun1,2; Tian, Yu-Xi1; Fu, Li-Min1; Wang, Tian-He1; Li, Hai-Jun1; Wang, Peng1; Han, Rul-Min1; Zhang, Jian-Ping1; Skibsted, Leif H.3
2008-11-12
Source PublicationJOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
ISSN0021-8561
Volume56Issue:21Pages:10376-10383
AbstractIsoflavone claidzein (D, pK(a1) = 7.47 +/- 0.02 and pK(a2) = 9.65 +/- 0.07) was, through a study of the parent compound and its three methyl anisol derivatives 7-methyidaidzein (7-Me-D, pK(a) = 9.89 +/- 0.05), 4'-methyldaidzein (4'-Me-D, pK(a) = 7.43 +/- 0.03), and 7,4'-dimethyldaidzein (7,4'-diMe-D), found to retard lipid oxidation in liposomal membranes through two mechanisms: (i) radical scavenging for which the 4'-OH was more effective than the 7-OH group in agreement with the oxidation potentials: 0.69 V for 4'-OH and 0.92 V for 7-OH versus Ag/AgCl in acidic solution and 0.44 V for 4'-O- and 0.49 V for 7-O- in alkaline solution and (ii) change in membrane fluidity through incorporation of the isoflavones, in effect hampering radical mobility. The radical scavenging efficiency measured by the rate of the reaction with the ABTS(center dot+) in aqueous solution followed the order D > 7-Me-D > 4'-Me-D > 7,4'-diMe-D, as also found for antioxidant efficiency in liposomes when oxidation was initiated with the water-soluble AAPH radical and monitored as the formation of conjugate dienes. For oxidation initiated by the lipid-soluble AMVN radical, the antioxidant efficiency was ranked as 4'-Me-D > D > 7,4'-diMe-D > 7-Me-D, and change in fluorescence anisotropy of fluorescent probes bound to the membrane surface or inside the lipid bilayer confirmed the effects of isoflavones on the membrane fluidity, especially for 7,4'-diMe-D.
KeywordDaidzein Derivative Liposome Radical Scavenge Antioxidation
DOI10.1021/jf801907m
Indexed BySCI
Language英语
WOS IDWOS:000260675600089
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:28[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/64930
Collection中国科学院化学研究所
Corresponding AuthorZhang, Jian-Ping
Affiliation1.Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China
2.Chinese Acad Sci, Inst Chem, State Key Lab Struct Chem Unstable & Stable Speci, Beijing 100080, Peoples R China
3.Univ Copenhagen, Dept Food Sci, Fac Life Sci, DK-1058 Frederiksberg C, Denmark
Recommended Citation
GB/T 7714
Liang, Jun,Tian, Yu-Xi,Fu, Li-Min,et al. Daidzein as an Antioxidant of Lipid: Effects of the Microenvironment in Relation to Chemical Structure[J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,2008,56(21):10376-10383.
APA Liang, Jun.,Tian, Yu-Xi.,Fu, Li-Min.,Wang, Tian-He.,Li, Hai-Jun.,...&Skibsted, Leif H..(2008).Daidzein as an Antioxidant of Lipid: Effects of the Microenvironment in Relation to Chemical Structure.JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,56(21),10376-10383.
MLA Liang, Jun,et al."Daidzein as an Antioxidant of Lipid: Effects of the Microenvironment in Relation to Chemical Structure".JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 56.21(2008):10376-10383.
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