Mushroom tyrosinase inhibition activity of some chromones.
Currently, aloesin is used in the cosmetic industry as a whitening agent because it inhibits tyrosinase activity. Aloesin is a C-glycosylated chromone compound isolated from aloe, and it is difficult to synthesize because of C-glycosyl moiety in the molecule. The purpose of this study is to search for a new chromone compound which is easy to synthesize and which posesses stronger tyrosinase inhibitory activity than aloesin. Fourteen chromone derivatives were synthesized and screened for their mushroom-tyrosinase inhibitory activity. 5-Methyl-7-methoxy-2-(2'-benzyl-3'-oxobutyl)chromone (15) showed the strongest activity among tested compounds. Its activity was not only stronger than aloesin, but also stronger than arbutin and kojic acid. The kinetic analysis revealed a competitive inhibition of 15 with tyrosinase for the L-tyrosine binding site.
Piao
Long Zhu
LZ
College of Pharmacy, Seoul National University, Korea.
Park
Hyang Rae
HR
Park
Yun Kyung
YK
Lee
Seung Ki
SK
Park
Jeong Hill
JH
Park
Man Ki
MK
D000363:Agaricales / Q000201:enzymology*; D002867:Chromones / Q000737:chemistry / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D005960:Glucosides / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D021241:Spectrometry, Mass, Electrospray Ionization
D002867:Chromones; D004791:Enzyme Inhibitors; D005960:Glucosides; D014442:Monophenol Monooxygenase; C069868:aloesin