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Molecules 2007, 12(5), 1045-1056; doi:10.3390/12051045
Article

Effects of Quercetin on Mushroom Tyrosinase and B16-F10 Melanoma Cells

* ,  and
Department of Environmental Science, Policy and Management, University of California, Berkeley, CA 94720-3114, USA
* Author to whom correspondence should be addressed.
Received: 12 April 2007 / Revised: 14 May 2007 / Accepted: 14 May 2007 / Published: 15 May 2007
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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Abstract

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 μM and almost complete lethality was observed at 80 μM.
Keywords: Quercetin; mushroom tyrosinase; adducts; murine B16-F10 melanoma cells; cytotoxicity Quercetin; mushroom tyrosinase; adducts; murine B16-F10 melanoma cells; cytotoxicity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Kubo, I.; Nitoda, T.; Nihei, K.-I. Effects of Quercetin on Mushroom Tyrosinase and B16-F10 Melanoma Cells. Molecules 2007, 12, 1045-1056.

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