Flavonols from saffron flower: tyrosinase inhibitory activity and inhibition mechanism.
A common flavonol, kaempferol, isolated from the fresh flower petals of Crocus sativus L. (Iridaceae) was found to inhibit the oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA) catalyzed by mushroom tyrosinase with an ID(50) of 67 microgram/mL (0.23 mM). Interestingly, its 3-O-glycoside derivatives did not inhibit this oxidation. The inhibition kinetics analyzed by a Lineweaver-Burk plot found kaempferol to be a competitive inhibitor, and this inhibitory activity presumably comes from its ability to chelate copper in the enzyme. This copper chelation mechanism can be applicable for all of the flavonols as long as their 3-hydroxyl group is free. However, quercetin, kaempferol, and galangin each affect the oxidation of L-tyrosine in somewhat different ways.
Kubo
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Department of Environmental Science, University of California, Berkeley, California 94720-3112, USA. ikubo@uclink4.berkeley.edu
Kinst-Hori
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D005419:Flavonoids / Q000737:chemistry* / Q000302:isolation & purification; D006801:Humans; D044949:Kaempferols; D019668:Liliaceae; D008543:Melanins / Q000037:antagonists & inhibitors; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D010936:Plant Extracts / Q000737:chemistry; D011794:Quercetin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification
D005419:Flavonoids; D044949:Kaempferols; D008543:Melanins; D010936:Plant Extracts; C006552:kaempferol; D011794:Quercetin; D014442:Monophenol Monooxygenase