Structural criteria for depigmenting mechanism of arbutin.
Arbutin, hydroquinone-O-beta-D-glucopyranoside (1) was found to inhibit the oxidation of l-tyrosine (monophenolase activity) catalyzed by mushroom tyrosinase. However, arbutin itself was oxidized as a monophenol substrate at an extremely slow rate, and this oxidation was accelerated as soon as catalytic amounts (0.01 mM) of l-3,4-dihydroxyphenylalanine (L-DOPA) became available as a cofactor. The result observed was supported by monitoring oxygen consumption. The depigmenting mechanism of arbutin previously reported is supportable if a cofactor is not available in the melanocytes. The combination with L-ascorbic acid is a useful application, particularly when oxygen is limited.
Hori
Ikuyo
I
Department of Environmental Science, Policy and Management, University of California, Berkeley, CA, USA.
Nihei
Ken-ichi
K
Kubo
Isao
I
D000363:Agaricales; D001104:Arbutin / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D008544:Melanocytes / Q000187:drug effects*; D014442:Monophenol Monooxygenase / Q000187:drug effects*; D010084:Oxidation-Reduction; D008517:Phytotherapy; D010858:Pigmentation / Q000187:drug effects*
D001104:Arbutin; D014442:Monophenol Monooxygenase