Methyl p-coumarate, a melanin formation inhibitor in B16 mouse melanoma cells.
p-Coumaric acid (4-hydroxycinnamic acid) and methyl p-coumarate (methyl 4-hydroxycinnamate) inhibit the oxidation of L-tyrosine catalyzed by mushroom tyrosinase. However, both were oxidized as monophenol substrate analogues at an extremely slow rate. This oxidation was significantly accelerated as soon as catalytic amounts (0.01 mM) of L-3,4-dihydroxyphenylalanine (L-DOPA) became available as a co-factor. Methyl p-coumarate significantly suppressed the melanin formation in B16 mouse melanoma cells, whereas p-coumaric acid did not show this activity.
Kubo
Isao
I
Department of Environmental Science, Policy and Management, University of California, Berkeley, CA 94720-3112, USA. ikubo@uclink.berkeley.edu
Nihei
Ken-ichi
K
Tsujimoto
Kazuo
K
D000818:Animals; D003373:Coumaric Acids / Q000737:chemistry / Q000494:pharmacology; D008543:Melanins / Q000096:biosynthesis*; D008546:Melanoma, Experimental; D051379:Mice; D011422:Propionates; D014407:Tumor Cells, Cultured; D014443:Tyrosine / Q000378:metabolism
D003373:Coumaric Acids; D008543:Melanins; D011422:Propionates; D014443:Tyrosine; C495469:p-coumaric acid