Puerarin and conjugate bases as radical scavengers and antioxidants: Molecular mechanism and synergism with beta-carotene

doi:10.1021/jf062796c

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	Puerarin and conjugate bases as radical scavengers and antioxidants: Molecular mechanism and synergism with beta-carotene
	Han, Rui-Min ; Tian, Yu-Xi ; Becker, Eleonora Miquel ; Andersen, Mogens L.; Zhang, Jian-Ping ; Skibsted, Leif H.
刊名	JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
	2007-03-21
卷号	55 期号:6 页码:2384-2391
关键词	Puerarin Beta-carotene Radical Scavenging Antioxidant Synergism
ISSN号	0021-8561
DOI	10.1021/jf062796c
英文摘要	The 4'-hydroxyl group of puerarin, a C-glycoside of the isoflavonoid daidzein, was shown, using 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) radical cation and stopped-flow spectroscopy and by comparison with the 7-propylpuerarin (A ring derivative) and 4'-propylpuerarin (B ring derivative), to be a more efficient radical scavenger as compared to the 7-hydroxyl group by a factor of 2, a difference increasing upon deprotonation. The difference in radical scavenging agreed with the oxidation potentials (cyclic voltammetry in acetonitrile, 0.1 M Bu4NBF4 at 25 degrees C): E/mV = 862 +/- 3 for puerarin, 905 +/- 10 for 7-propylpuerarin, and 1064 +/- 2 for 4'-propylpuerarin relative to ferrocene/ferricenium. In aqueous solution, the reduction potential was shown to decrease for increasing pH, and deprotonation of the 4'-hydroxyl group increased radical scavenging more than deprotonation of the 7-hydroxyl group. The 7-hydroxyl was found to be more acidic (pK(a1) = 7.20 +/- 0.01 in puerarin and pK(a) = 7.23 +/- 0.01 in 4'-propylpuerarin) than the 4'-hydroxyl group (pK(a2) = 9.84 +/- 0.08 in puerarin and pK(a) = 9.51 +/- 0.02 in 7-propylpuerarin); aqueous solution, ionic strength of 0.1, and 25 degrees C. In phosphatidyl choline liposome of pH 7.4, puerarin and beta-carotene each showed a modest antioxidant activity measured as prolongation of the lag phase for formation of conjugate dienes and using the water-soluble radical initiator APPH with effects of puerarin and beta-carotene being additive. For the lipophilic initiator AMVN, the antioxidative effect decreased for puerarin and increased for beta-carotene as compared to APPH and showed a clear synergism. A regeneration of beta-carotene, effective in the liposome lipid phase as antioxidant, from the cation radical by deprotonated forms of puerarin was demonstrated in 9:1 chloroform/methanol using laser flash photolysis with k(2) = 2.7 x 10(4) L mol(-1) s(-1) for the bimolecular process between the cation radical and the puerarin dianion.
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000244867300047
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/60581]
专题	中国科学院化学研究所
通讯作者	Skibsted, Leif H.
作者单位	1.Royal Vet & Agr Univ, Dept Food Sci, DK-1958 Frederiksberg C, Denmark 2.Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China 3.Chinese Acad Sci, Inst Chem, State Key Lab Struct Chem Unstable & Stable Speci, Beijing 100080, Peoples R China
推荐引用方式 GB/T 7714	Han, Rui-Min,Tian, Yu-Xi,Becker, Eleonora Miquel,et al. Puerarin and conjugate bases as radical scavengers and antioxidants: Molecular mechanism and synergism with beta-carotene[J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,2007,55(6):2384-2391.
APA	Han, Rui-Min,Tian, Yu-Xi,Becker, Eleonora Miquel,Andersen, Mogens L.,Zhang, Jian-Ping,&Skibsted, Leif H..(2007).Puerarin and conjugate bases as radical scavengers and antioxidants: Molecular mechanism and synergism with beta-carotene.JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,55(6),2384-2391.
MLA	Han, Rui-Min,et al."Puerarin and conjugate bases as radical scavengers and antioxidants: Molecular mechanism and synergism with beta-carotene".JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 55.6(2007):2384-2391.