Daidzein as an Antioxidant of Lipid: Effects of the Microenvironment in Relation to Chemical Structure

doi:10.1021/jf801907m

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	Daidzein as an Antioxidant of Lipid: Effects of the Microenvironment in Relation to Chemical Structure
	Liang, Jun 1,2; Tian, Yu-Xi 1; Fu, Li-Min 1; Wang, Tian-He 1; Li, Hai-Jun 1; Wang, Peng 1; Han, Rul-Min 1; Zhang, Jian-Ping 1; Skibsted, Leif H.3
刊名	JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
	2008-11-12
卷号	56 期号:21 页码:10376-10383
关键词	Daidzein Derivative Liposome Radical Scavenge Antioxidation
ISSN号	0021-8561
DOI	10.1021/jf801907m
英文摘要	Isoflavone 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.
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000260675600089
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/64929]
专题	中国科学院化学研究所
通讯作者	Zhang, Jian-Ping
作者单位	1.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
推荐引用方式 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.