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

Isao Kubo, Teruhiko Nitoda, Ken Ichi Nihei

Research output: Contribution to journalArticle

44 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1045-1056
Number of pages12
JournalMolecules
Volume12
Issue number5
DOIs
Publication statusPublished - May 2007
Externally publishedYes

Fingerprint

Experimental Melanomas
Monophenol Monooxygenase
Agaricales
Quercetin
dopa
Levodopa
quinones
adducts
cells
lethality
melanin
Quinones
Flavonols
Melanins
Catalysis
Hydroxyl Radical
inhibitors
catalysis
Cultured Cells
Substrates

Keywords

  • Adducts
  • Cytotoxicity
  • Murine B16-F10 melanoma cells
  • Mushroom tyrosinase
  • Quercetin

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Effects of quercetin on mushroom tyrosinase and B16-F10 melanoma cells. / Kubo, Isao; Nitoda, Teruhiko; Nihei, Ken Ichi.

In: Molecules, Vol. 12, No. 5, 05.2007, p. 1045-1056.

Research output: Contribution to journalArticle

Kubo, Isao ; Nitoda, Teruhiko ; Nihei, Ken Ichi. / Effects of quercetin on mushroom tyrosinase and B16-F10 melanoma cells. In: Molecules. 2007 ; Vol. 12, No. 5. pp. 1045-1056.
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