Effects of matsutake mushroom scent compounds on tyrosinase and murine B16-F10 melanoma cells

• Published in: Biochemical and biophysical research communications Vol. 487; no. 4; pp. 840 - 846
• Main Authors: Satooka, Hiroki, Cerda, Philip, Kim, Hae-Jung, Wood, William F., Kubo, Isao
• Format: Journal Article
• Language: English
• Published: United States Elsevier Inc 10.06.2017
• Subjects: 3,5-Dichloro-4-methoxybenzaldehyde; 60 APPLIED LIFE SCIENCES; ANIMAL CELLS; Animals; Cell Survival - drug effects; Cinnamates - chemistry; Cinnamates - isolation & purification; Cinnamates - pharmacology; Dose-Response Relationship, Drug; DOUBLE BONDS; Enzyme Inhibitors - chemistry; Enzyme Inhibitors - isolation & purification; Enzyme Inhibitors - pharmacology; INHIBITION; Matsutake mushroom; MELANIN; Melanogenesis; Melanoma, Experimental - drug therapy; Melanoma, Experimental - enzymology; Melanoma, Experimental - pathology; MELANOMAS; Methyl cinnamate; Mice; Monophenol Monooxygenase - antagonists & inhibitors; Monophenol Monooxygenase - metabolism; Murine B16-F10 melanoma cells; MUSHROOMS; Odorants; OXIDATION; PLANT GROWTH; Structure-Activity Relationship; TOXICITY; Tricholoma - chemistry; Tricholoma - enzymology; Tumor Cells, Cultured; TYROSINASE; Matsutake mushroom; Melanogenesis; 3,5-Dichloro-4-methoxybenzaldehyde; Murine B16-F10 melanoma cells; Methyl cinnamate; Tyrosinase
• ISSN: 0006-291X; 1090-2104
• DOI: 10.1016/j.bbrc.2017.04.137

Tyrosinase-catalyzed l-tyrosine oxidation is a key step in melanogenesis, and intense melanin formation is often a problem in chemotherapies or food preservation. Here we report that methyl cinnamate one of the constituents characterized from mycelium and sporocarp of American matsutake mushroom Tricholoma magnivelare inhibits both enzymatic and cellular melanin formation. Methyl cinnamate inhibits mushroom tyrosinase-catalyzed l-tyrosine oxidation while the oxidation of l-3,4-dihydroxyphenylalanine (l-DOPA) was not inhibited. In subsequent cellular assays, methyl cinnamate significantly suppressed melanogenesis of murine B16-F10 melanoma cells without affecting cell growth. However, methyl 3-phenylpropionate, a dihydro-derivative of methyl cinnamate, did not possess melanogenesis, indicating that the double bond in the enone moiety is a key Michael reaction acceptor to elicit the activity. In addition, a rather rare chlorinated benzaldehyde derivative, 3,5-dichloro-4-methoxybenzaldehyde isolated from the same source, was found to show potent cytotoxicity, and the chlorine atom reduced a tyrosinase inhibitory activity but enhanced cytotoxicity. Our findings suggest that methyl cinnamate is a novel melanogenesis inhibitor from natural sources. •Methyl cinnamate in matsutake mushroom inhibits l -tyrosine oxidation by tyrosinase.•Methyl cinnamate suppressed melanogenesis in melanocytes without cytotoxicity.•Michael reaction of enone moiety in methyl cinnamate is a key mode of action.•Chlorine atom reduced inhibitory activity on tyrosinase but enhanced cytotoxicity.