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Prooxidant activity of hydroxycinnamic acids on DNA damage in the presence of Cu(II) ions: Mechanism and structure-activity, relationship
Zheng, LF; Dai, F(戴芳); Zhou, B(周波); Yang, L; Liu, ZL(刘中立); Zhou, B (reprint author), Lanzhou Univ, Natl Lab Appl Organ Chem, Lanzhou 730000, Peoples R China.
Indexed BySCIE ; PubMed ; MEDLINE ; BIOSIS
2008-01
Source PublicationFOOD AND CHEMICAL TOXICOLOGY
Volume46Issue:1
PublisherELSEVIER
Publication PlaceOXFORD
AbstractThe prooxidant effect of hydroxycinnamic acids (HCAs), i.e., caffeic acid (CaA), chlorogenic acid (ChA), sinapic acid (SA), ferulic acid (FA), 3-hydroxycinnamic acid (3-HCA) and 4-hydroxycinnamic acid (4-HCA) on supercoiled pBR322 plasmid DNA strand breakage and calf thymus DNA damage in the presence of Cu(II) ions has been studied. It was found that the compounds bearing ortho-dihydroxyl group (CaA and ChA) or bearing 4-hydroxy-3-methoxyl group (SA and FA) exhibited remarkably higher activity in the DNA damage than the ones bearing no such functionalities. The good correlation between the DNA damaging activity and the oxidative potential of the compounds indicates that the electron transfer between HCAs and Cu(II) plays a crucial role in the reaction. UV-Visible spectral changes demonstrated that CaA or ChA can chelate with Cu(II) as a bidentate ligand, hence facilitating intramolecular electron transfer between CaA or ChA and Cu(II). The involvement of reactive oxygen species (ROS) and Cu(I) ions in the DNA damage were affirmed by the inhibition of DNA breakage using mannitol, glutathione (GSH), catalase and bathocuproinedisulfonic acid (BCDS). These results may have important implications regarding the proposed mechanism of apoptosis induced by phenol and endogenous metal ions. (c) 2007 Elsevier Ltd. All rights reserved.
Keywordhydroxycinnamate caffeic acid DNA damage copper structure activity relationship reactive oxygen species
Department[Zheng, Li-Fang;
Dai, Fang;
Zhou, Bo;
Yang, Li;
Liu, Zhong-Li] Lanzhou Univ, Natl Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
Subject AreaFood Science & Technology ; Toxicology
DOI10.1016/j.fct.2007.07.010
ISSN0278-6915
SubtypeArticle
Language英语
WOS IDWOS:000253036900018
PMID 17764801
BIOSIS IDBIOSIS:PREV200800177347
First Inst
Citation statistics
Cited Times:63[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.lzu.edu.cn/handle/262010/77740
Collection化学化工学院
Corresponding AuthorZhou, B (reprint author), Lanzhou Univ, Natl Lab Appl Organ Chem, Lanzhou 730000, Peoples R China.
Recommended Citation
GB/T 7714
Zheng, LF,Dai, F,Zhou, B,et al. Prooxidant activity of hydroxycinnamic acids on DNA damage in the presence of Cu(II) ions: Mechanism and structure-activity, relationship[J]. FOOD AND CHEMICAL TOXICOLOGY,2008,46(1).
APA Zheng, LF,Dai, F,Zhou, B,Yang, L,Liu, ZL,&Zhou, B .(2008).Prooxidant activity of hydroxycinnamic acids on DNA damage in the presence of Cu(II) ions: Mechanism and structure-activity, relationship.FOOD AND CHEMICAL TOXICOLOGY,46(1).
MLA Zheng, LF,et al."Prooxidant activity of hydroxycinnamic acids on DNA damage in the presence of Cu(II) ions: Mechanism and structure-activity, relationship".FOOD AND CHEMICAL TOXICOLOGY 46.1(2008).
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