Influence of side chain structure changes on antioxidant potency of the [6]-gingerol related compounds

Authors：Lu Dong Liang; Li Xiu Zhuang; Dai Fang^*; Kang Yan Fei; Li Yan; Ma Meng Meng; Ren Xiao Rong; Du Gao Wei; Jin Xiao Ling; Zhou Bo

Source：Food Chemistry, 2014, 165: 191-197.

DOI：10.1016/j.foodchem.2014.05.077

• Gingerol
• Shogaol
• Antioxidant
• DNA damage
• Lipid peroxidation

161-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 C-1-C-2 double bond, the C-4-C-5 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.

• Institution
  兰州大学