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Tyrosinase inhibitory effects and antioxidative activities of novel cinnamoyl amides with amino acid ester moiety.
MedLine Citation:
PMID:  23107731     Owner:  NLM     Status:  In-Data-Review    
Abstract/OtherAbstract:
Nine cinnamoyl amides with amino acid ester (CAAE) moiety were synthesized by the conjugation of the corresponding cinnamic acids (cinnamic acid, 4-hydroxy cinnamic acid, ferulic acid and caffeic acid) with amino acid esters, and their inhibitory effects on the activities of mushroom tyrosinase were investigated, using l-3,4-dihydroxyl-phenylalanine (l-DOPA) as the substrate. Among these CAAE amides, ethyl N-[3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]-l-phenylalaninate (b(4)) showed the strongest inhibitory activity; the IC(50) was 0.18μM. The IC(50) values, inhibition types, inhibition mechanisms and kinetics of all these CAAE amides were evaluated. A structure-activity relationship (SAR) study found that the inhibitory effects were potentiated with the increasing length of hydrocarbon chains at the amino acid esters and also influenced by the substituents at the styrene groups. Furthermore, the hydroxyl radical scavenging and anti-lipid peroxidation activities of four CAAE derivatives were also investigated. Among these compounds, b(3) (ethyl N-[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]-l-phenylalaninate) and b(4) exhibited potential antioxidant activities.
Authors:
Qian Fan; Hong Jiang; Er-Dong Yuan; Jian-Xun Zhang; Zheng-Xiang Ning; Sui-Jian Qi; Qing-Yi Wei
Publication Detail:
Type:  Journal Article     Date:  2012-03-16
Journal Detail:
Title:  Food chemistry     Volume:  134     ISSN:  0308-8146     ISO Abbreviation:  Food Chem     Publication Date:  2012 Sep 
Date Detail:
Created Date:  2012-10-30     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7702639     Medline TA:  Food Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  1081-7     Citation Subset:  IM    
Copyright Information:
Copyright © 2012 Elsevier Ltd. All rights reserved.
Affiliation:
College of Light Industry and Food Science, South China University of Technology, Guangzhou 510640, Guangdong, PR China.
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