Effects of quercetin on mushroom tyrosinase and B16-F10 melanoma cells

In searching for tyrosinase inhibitors from plants using L-3,4-dihydroxyphenylalanine (L-DOPA) as a substrate, quercetin was found to be partially oxidized to the corresponding o-quinone under catalysis by mushroom tyrosinase (EC 1.14.18.1). Simultaneously, L-DOPA was also oxidized to dopaquinone an...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2007-05, Vol.12 (5), p.1045-1056
Main Authors: Kubo, Isao, Nitoda, Teruhiko, Nihei, Ken-ichi
Format: Article
Language:English
Subjects:
adducts
Agaricales - enzymology
Animals
Catalysis
Cell Line, Tumor
cytotoxicity
Enzyme Inhibitors - pharmacology
Enzymes
Kinetics
Melanins - biosynthesis
Melanoma
Melanoma, Experimental - metabolism
Melanoma, Experimental - pathology
Monophenol Monooxygenase - antagonists & inhibitors
murine B16-F10 melanoma cells
mushroom tyrosinase
Oxidation
Quercetin
Quercetin - pharmacology
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Summary:In searching for tyrosinase inhibitors from plants using L-3,4-dihydroxyphenylalanine (L-DOPA) as a substrate, quercetin was found to be partially oxidized to the corresponding o-quinone under catalysis by mushroom tyrosinase (EC 1.14.18.1). Simultaneously, L-DOPA was also oxidized to dopaquinone and both o-quinones were further oxidized, respectively. The remaining quercetin partially formed adducts with dopaquinone through a Michael type addition. In general, flavonols form adducts with dopaquinone as long as their 3-hydroxyl group is free. Quercetin enhanced melanin production per cell in cultured murine B16-F10 melanoma cells, but this effect may be due in part to melanocytotoxicity. The concentration leading to 50% viable cells lost was established as 20 microM and almost complete lethality was observed at 80 microM.
ISSN:1420-3049
1420-3049
DOI:10.3390/12051045