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Tyrosinase inhibitory effects and antioxidative activities of novel cinnamoyl amides with amino acid ester moiety.

Food chemistry (2012-10-31)
Qian Fan, Hong Jiang, Er-Dong Yuan, Jian-Xun Zhang, Zheng-Xiang Ning, Sui-Jian Qi, Qing-Yi Wei
ABSTRACT

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 0.18 μM. 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.

MATERIALS
Product Number
Brand
Product Description

Supelco
trans-Cinnamic acid, analytical standard
Sigma-Aldrich
trans-Cinnamic acid, 97%
Sigma-Aldrich
trans-Cinnamic acid, ≥99%
Sigma-Aldrich
trans-Cinnamic acid, natural, ≥99%, FCC, FG
Sigma-Aldrich
trans-Cinnamic acid, ≥99%, FG