title: An effective strategy to develop active cinnamic acid-directed antioxidants based on elongating the conjugated chains.
abstract: To optimize antioxidant activity and lipophilicity of cinnamic acid derivatives (CAs) including ferulic acid, sinapic acid, 3,4-dimethoxycinnamic acid, and p-hydroxycinnamic acid, four analogs bearing an additional double bond between their aromatic ring and propenoic acid moiety were designed and synthesized based on the conjugated chain elongation strategy. The antioxidant performance of the CAs were investigated by 2,2'-diphenyl-1-picrylhydrazyl (DPPH)-scavenging, ferric reducing/antioxidant power, cyclic voltammetry, DNA strand breakage-inhibiting and anti-haemolysis activity assays. It was found that CAs with elongation of conjugated chains display increased DPPH-scavenging, DNA strand breakage-inhibiting and anti-haemolysis activities as compared to their parent molecules, due to their improved hydrogen atom-donating ability and lipophilicity. Overall, this work highlights an effective strategy to develop potential CA-directed antioxidants by elongating their conjugated chain.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Li
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China. Electronic address: daifang@lzu.edu.cn.
authors.forename: Fang
authors.initials: F
authors.lastname: Dai
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China.
authors.forename: Xiao-Ling
authors.initials: XL
authors.lastname: Jin
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China.
authors.forename: Meng-Meng
authors.initials: MM
authors.lastname: Ma
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China.
authors.forename: Yi-Hua
authors.initials: YH
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China.
authors.forename: Xiao-Rong
authors.initials: XR
authors.lastname: Ren
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China. Electronic address: bozhou@lzu.edu.cn.
authors.forename: Bo
authors.initials: B
authors.lastname: Zhou
mesh_terms: D000975:Antioxidants / Q000737:chemistry*; D002934:Cinnamates / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D059808:Polyphenols
chemical_list: D000975:Antioxidants; D002934:Cinnamates; D059808:Polyphenols; C029010:cinnamic acid
keywords: Antioxidant; Cinnamic acid; Conjugated chain; Lipophilicity; Redox potential