title: Influence of side chain structure changes on antioxidant potency of the [6]-gingerol related compounds.
abstract: [6]-Gingerol and [6]-shogaol are the major pungent components in ginger with a variety of biological activities including antioxidant activity. To explore their structure determinants for antioxidant activity, we synthesized eight compounds differentiated by their side chains which are characteristic of the C1-C2 double bond, the C4-C5 double bond or the 5-OH, and the six- or twelve-carbon unbranched alkyl chain. Our results show that their antioxidant activity depends significantly on the side chain structure, the reaction mediums and substrates. Noticeably, existence of the 5-OH decreases their formal hydrogen-transfer and electron-donating abilities, but increases their DNA damage- and lipid peroxidation-protecting abilities. Additionally, despite significantly reducing their DNA strand breakage-inhibiting activity, extension of the chain length from six to twelve carbons enhances their anti-haemolysis activity.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China.
authors.forename: Dong-Liang
authors.initials: DL
authors.lastname: Lu
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China.
authors.forename: Xiu-Zhuang
authors.initials: XZ
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: Yan-Fei
authors.initials: YF
authors.lastname: Kang
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.
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: Xiao-Rong
authors.initials: XR
authors.lastname: Ren
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China.
authors.forename: Gao-Wei
authors.initials: GW
authors.lastname: Du
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. Electronic address: bozhou@lzu.edu.cn.
authors.forename: Bo
authors.initials: B
authors.lastname: Zhou
mesh_terms: D000975:Antioxidants / Q000737:chemistry*; D002396:Catechols / Q000737:chemistry*; D004249:DNA Damage; D005233:Fatty Alcohols / Q000737:chemistry*; D015227:Lipid Peroxidation; D010936:Plant Extracts / Q000737:chemistry*
chemical_list: D000975:Antioxidants; D002396:Catechols; D005233:Fatty Alcohols; D010936:Plant Extracts; C040115:shogaol; C007845:gingerol
keywords: Antioxidant; DNA damage; Gingerol; Lipid peroxidation; Shogaol