A newly synthesized, potent tyrosinase inhibitor: 5-(6-hydroxy-2-naphthyl)-1,2,3-benzenetriol.
In searching for new agents with a depigmenting effect, we synthesized a derivative of resveratrol, 5-(6-hydroxy-2-naphthyl)-1,2,3-benzenetriol (5HNB) with a potent tyrosinase inhibitory activity. 5HNB inhibited mushroom tyrosinase with an IC(50) value of 2.95 microM, which is more potent than the well-known anti-tyrosinase activity of kojic acid (IC(50)=38.24). The results of the enzymatic inhibition kinetics by Lineweaver-Burk analysis indicated 5HNB inhibits tyrosinase non-competitively when L-tyrosine was used as the substrate. Based on the strong inhibitory action of 5HNB, it is expected that 5HNB can suppress melanin production in which tyrosinase plays the essential role. Our expectation was confirmed by the experimentations with B16 melanoma cells in which 5HNB inhibited melanin production. We propose that 5HNB might have skin-whitening effects as well as therapeutic potential for treating skin pigmentation disorders.
Choi
Jehun
J
Department of Pharmacy and Molecular Inflammation Research Center for Aging Intervention (MRCA), Pusan National University, Gumjung-gu, Busan 609-735, Republic of Korea.
Bae
Sung Jin
SJ
Ha
Young Mi
YM
No
Jae Kyung
JK
Lee
Eun Kyeong
EK
Lee
Jun Sik
JS
Song
Suhee
S
Lee
Hyojin
H
Suh
Hongsuk
H
Yu
Byung Pal
BP
Chung
Hae Young
HY
D000363:Agaricales / Q000201:enzymology; D000818:Animals; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D007700:Kinetics; D008543:Melanins / Q000096:biosynthesis; D008546:Melanoma, Experimental / Q000378:metabolism; D051379:Mice; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D009284:Naphthols / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D011748:Pyrogallol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011753:Pyrones / Q000494:pharmacology; D000077185:Resveratrol; D013267:Stilbenes / Q000494:pharmacology
C553343:5-(6-hydroxy-2-naphthyl)-1,2,3-benzenetriol; D004791:Enzyme Inhibitors; D008543:Melanins; D009284:Naphthols; D011753:Pyrones; D013267:Stilbenes; D011748:Pyrogallol; C011890:kojic acid; D014442:Monophenol Monooxygenase; D000077185:Resveratrol