Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on mushroom tyrosinase.
A novel tyrosinase inhibitor, an arbutin derivative having undecylenic acid at the 6-position of its glucose moiety, was enzymatically synthesized. Its inhibitory activity was studied in vitro by using catechol and phenol as substrates. The IC(50) value of the arbutin ester on tyrosinase using catechol (4 x 10(-4) M) was 1% of that when arbutin (4 x 10(-2) M) was used. Using phenol, IC(50) of the arbutin ester (3 x 10(-4) M) as substrate was 10% of that of arbutin (3 x 10(-3) M). These results suggest that the arbutin ester inhibits the latter part of the tyrosinase reaction, which consists of hydroxylation and oxidation.
Tokiwa
Y
Y
National Institute of Advanced Industrial Science and Technology, Central 6, 1-1-1 Higashi, Tsukuba, Ibaraki, Japan. y.tokiwa@aist.go.jp
Kitagawa
M
M
Raku
T
T
D000363:Agaricales / Q000201:enzymology*; D001104:Arbutin / Q000031:analogs & derivatives* / Q000737:chemistry; D001412:Bacillus subtilis / Q000201:enzymology*; D001426:Bacterial Proteins / Q000737:chemistry*; D010450:Endopeptidases / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D014476:Undecylenic Acids / Q000737:chemistry*
D001426:Bacterial Proteins; D004791:Enzyme Inhibitors; D004952:Esters; D014476:Undecylenic Acids; C521564:arbutin undecylenic acid ester; D001104:Arbutin; D014442:Monophenol Monooxygenase; D010450:Endopeptidases; C087822:alkaline protease