| RRC ID |
41926
|
| Author |
Ohguchi K, Tanaka T, Kido T, Baba K, Iinuma M, Matsumoto K, Akao Y, Nozawa Y.
|
| Title |
Effects of hydroxystilbene derivatives on tyrosinase activity.
|
| Journal |
Biochem Biophys Res Commun
|
| Abstract |
Synthesis of melanin starts from the conversion of L-tyrosine to 3,4-dihydroxyphenylalanine (L-dopa) and then the oxidation of L-dopa yields dopaquinone by tyrosinase. Therefore, tyrosinase inhibitors have been established as important constituents of depigmentation agents. Recently, polyhydroxystilbene compounds, which are trans-resveratrol (3,4('),5-trihydroxy-trans-stilbene) analogs, have been demonstrated as potent tyrosinase inhibitors. However, their detailed inhibitory mechanisms are not clearly understood. In the present study, a variety of synthesized hydroxystilbene compounds were tested for their inhibitory effects against murine tyrosinase activity. The inhibitory potencies of the hydroxy-trans-stilbene compounds were remarkably elevated by increasing number of phenolic hydroxy substituents. Methylated hydroxy-trans-stilbene lost the inhibitory activity. Furthermore, hydrogenated hydroxystilbene or hydroxy-cis-stilbene exerted little or no inhibitory effect compared with hydroxy-trans-stilbene on tyrosinase activity. The structure-activity relationships demonstrated in the present study suggest that the phenolic hydroxy groups and trans-olefin structure of the parent stilbene skeleton contribute to the inhibitory potency of hydroxystilbene for tyrosinase activity.
|
| Volume |
307(4)
|
| Pages |
861-3
|
| Published |
2003-8-8
|
| DOI |
10.1016/s0006-291x(03)01284-1
|
| PII |
S0006291X03012841
|
| PMID |
12878190
|
| MeSH |
Animals
Enzyme Inhibitors / chemistry*
Enzyme Inhibitors / pharmacology*
Mice
Monophenol Monooxygenase / metabolism*
Stilbenes / chemistry*
Stilbenes / pharmacology*
Structure-Activity Relationship
Tumor Cells, Cultured
|
| IF |
2.985
|
| Times Cited |
52
|
|
WOS Category
|
BIOPHYSICS
BIOCHEMISTRY & MOLECULAR BIOLOGY
|
| Resource |
| Human and Animal Cells |
B16 melanoma |
