GGG1黄烷酮的合成.pdfVIP

Bioorganic Medicinal Chemistry 15 (2007) 2396–2402 0 0 0 Synthesis and evaluation of 2 ,4 ,6 -trihydroxychalcones as a new class of tyrosinase inhibitors Nishida Jun, Gao Hong and Kawabata Jun* Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Kita-ku, Sapporo 060-8589, Japan Received 26 October 2006; revised 11 January 2007; accepted 12 January 2007 Available online 17 January 2007 Abstract—In this study, we synthesized a series of hydroxychalcones and examined their tyrosinase inhibitory activity. The results showed that 20 0 0 0 0 0 0 0 0 0 0 0 ,4 ,6 -trihydroxychalcone (1), 2,2 ,3,4 ,6 -pentahydroxychalcone (4), 2 ,3,4,4 ,5,6 -hexahydroxychalcone (5), 2 ,4 ,6 - trihydroxy- 3,4-dimethoxychalcone (9) and 2,20 0 0 ,4,4 ,6 -pentahydroxychalcone (15) exhibited high inhibitory effects on tyrosinase with respect to 0 0 0 LL-tyrosine as a substrate. By the structure–activity relationship study, it was suggested that the 2 ,4 ,6 -trihydroxyl substructure in the chalcone skeleton were efficacious for the inhibition of tyrosinase activity. And also, the catechol structure on B-ring of chalcones was not advantageous for the inhibitory potency. Furthermore, 15 (IC50 = 1 lM) was found to show the highest activity out of a set of 15 hydroxychalcones,