Shui-Ling Deng, Wei‐Feng Chen, Bo Zhou
2006
Citations
0
Influential Citations
59
Citations
Quality indicators
Journal
Food Chemistry
Abstract
Abstract Curcumin (1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione, 1 ), is a yellow ingredient isolated from turmeric ( curcumin longa ). It has been shown to exhibit a variety of biological activities, including antioxidative activity. In order to find more active antioxidants with 1 as the lead compound, we synthesized curcumin analogues, namely 1-(4-hydroxy-3- methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione ( 2 ), 1-(3,4-dimethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione ( 3 ), 1,7-bis(3,4-dimethoxyphenyl)-1,6-heptadiene-3,5-dione ( 4 ), 1-(3,4-dihydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione ( 5 ), 1,7-bis(3,4-dihydroxyphenyl)-1,6-heptadiene-3,5-dione ( 6 ), and 1,7-bis-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione ( 7 ), and evaluated their antioxidative activity. The in vitro oxidative haemolysis of human red blood cells (RBCs) was used as a model to study the free radical-induced damage of biological membranes and the protective effects of these curcumin analogues. It was found that these compounds, except 4 , could effectively inhibit the free radical induced oxidative haemolysis of RBCs by H-atom abstraction from the phenolic groups. Compounds 5 and 6 which bear ortho -diphenoxyl functionality exhibited markedly higher anti-haemolysis activity than curcumin and other analogues, as well as than α-tocopherol (vitamin E).