Benzyl benzoates: New phlorizin analogs as mushroom tyrosinase inhibitors.
In our research, 14 benzyl benzoates with hydroxyl(s) (3-16) were synthesized and their inhibitory activity on mushroom tyrosinase was tested. Results indicated that among these compounds, 4-hydroxybenzyl 3,5-dihydroxybenzoate (3), 4-hydroxybenzyl 2,4-dihydroxybenzoate (5), 4-hydroxybenzyl 2,4,6-dihydroxybenzoate (7), 3-hydroxybenzyl 3,5-dihydroxybenzoate (8), 3-hydroxybenzyl 2,4-dihydroxybenzoate (10) exhibited inhibitory activity with their IC(50) less than 10μM. Further studies showed these five compounds were competitive inhibitors of tyrosinase and their structure-activity relationships were investigated in this article.
Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Sun Yat-sen University, PR China.
Yuntai
Y
Fang
Yaozong
Y
Chen
Guanfeng
G
Feng
Lin
L
Ma
D000363:Agaricales / Q000201:enzymology; D003358:Cosmetics; D055808:Drug Discovery; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005519:Food Preservation; D020128:Inhibitory Concentration 50; D007700:Kinetics; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D010695:Phlorhizin / Q000031:analogs & derivatives*; D012459:Salicylates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
C560450:4-hydroxybenzyl 2,4-dihydroxybenzoate; D003358:Cosmetics; D004791:Enzyme Inhibitors; D012459:Salicylates; D010695:Phlorhizin; D014442:Monophenol Monooxygenase