Cinnamic acid derivatives active oxygen scavenging and xanthine oxidase? Inhibitory activity of the structure - activity relationship analysis
The structure-activity relationship of cinnamic acid derivatives on reactive oxygen species scavenging and xanthine oxidase inhibitory activities
Abstract
Phenolic compounds widely present in plants is extremely important to plant secondary chemical products. The second
category in which phenolic compounds (Phenolics Ⅱ) is a C 6 - C 3 of cinnamic acid (cinnamic acid)-based structure, in the benzene ring with one or more hydroxyl groups / methoxy groups or to replace the use of different ester groups are derived from its various
derivatives. The second category is known for Phenolic compounds have many physiological functions and drug activity in the xanthine oxidase? (Xanthine oxidase) is considered the early inflammatory reaction with ROS and cause gout. Pre-existing type II phenolic compounds in the inhibition of xanthine oxidase? The study, while the second class of phenolic compounds and enzyme structure - activity relationship (SAR) has been raised for discussion. However, in the second class of phenolic compounds and the Xanthine? Of three-dimensional chemical structure of the correlation is unknown.
In this study, we chose 11 different cinnamic acid derivatives, using DNA lysis test, DPPH scavenging and ESR techniques to see 11 species of this second type of phenolic compounds in the
antioxidant, radical trapping ability performance. In addition, we investigate the inhibition of the XO, and the use of enzyme kinetics to the inhibition pattern of molecular simulation to further explain the structure - activity relationship.
We found that caffeic acid (caffeic acid) has the best free radical scavenging effect, suggesting that the structure of aromatic ring substituents on the number of species and hydroxyl radical scavenging effect of the. Power analysis revealed a competitive type inhibition pattern, the simulation confirmed that the active
center of the bit with XO (docking) found that cinnamic acid derivatives with aromatic ring substrate binding site of
phenylalanine (phe) 914 具 π - π overlap force, carboxyl terminal acid radical (COOH) with XO? serine (Ser) 876 of the OH hydrogen bonding. Alignment, between spaces and adjacent spaces on the hydroxyl groups and arginine, respectively (Arg) 880, threonine (Thr) 1010 of the hydroxyl groups and, moreover, were located on the hydroxyl at the same time and (Thr) 1010 wins? key (-NH-) formed hydrogen bonds.
11 compounds, the caffeic acid phenethyl ester (caffeic acid
phenethyl ester) inhibit the enzyme activity of the best, suggesting that the aromatic ring hydroxyl groups, and away from water with a benzene ring structure, can help more accessible to XO? the enzyme active site. Based on the results, measured using ESR
Hypoxanthine / XO ROS generated by reaction, so it may reflect the tested compounds for the inhibition of XO and ROS scavenging activity generated for the overall index. The results showed that, caffeic acid and CAPE in all the compounds tested the best activity.
English Abstract
