Methyl p-coumarate, a melanin formation inhibitor in B16 mouse melanoma cells

被引：38

作者：

Kubo, I ^{[1
]}

Nihei, K

Tsujimoto, K

机构：

[1] Univ Calif Berkeley, Dept Environm Sci Policy & Management, Berkeley, CA 94720 USA

[2] JAIST, Sch Mat Sci, Tatsunokuchi, Ishikawa 9231292, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2004年 / 12卷 / 20期

关键词：

mushroom tyrosinase; monophenolase; p-coumaric acid; methyl p-coumarate; B16 mouse melanoma cell;

D O I：

10.1016/j.bmc.2004.07.052

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5349 / 5354

页数：6

共 27 条

[1] A COMPARISON OF MUSHROOM TYROSINASE DOPAQUINONE AND DOPACHROME ASSAYS USING DIODE-ARRAY SPECTROPHOTOMETRY - DOPACHROME FORMATION VS ASCORBATE-LINKED DOPAQUINONE REDUCTION [J].

BEHBAHANI, I ;

MILLER, SA ;

OKEEFFE, DH .

MICROCHEMICAL JOURNAL, 1993, 47 (1-2) :251-260

[2] Evidence of the indirect formation of the catecholic intermediate substrate responsible for the autoactivation kinetics of tyrosinase [J].

Cooksey, CJ ;

Garratt, PJ ;

Land, EJ ;

Pavel, S ;

Ramsden, CA ;

Riley, PA ;

Smit, NPM .

JOURNAL OF BIOLOGICAL CHEMISTRY, 1997, 272 (42) :26226-26235

[3] Natural products and plant disease resistance [J].

Dixon, RA .

NATURE, 2001, 411 (6839) :843-847

[4] Slow-binding inhibition of mushroom (Agaricus bisporus) tyrosinase isoforms by tropolone [J].

Espín, JC ;

Wichers, HJ .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1999, 47 (07) :2638-2644

[5]

GEESSINERPRETTR.C, 1992, ARCH BIOCHEM BIOPHYS, V296, P247

[6] Direct spectrophotometric assay of monooxygenase and oxidase activities of mushroom tyrosinase in the presence of synthetic and natural substrates [J].

Haghbeen, K ;

Tan, EW .

ANALYTICAL BIOCHEMISTRY, 2003, 312 (01) :23-32

[7] Cytotoxic and antioxidative sesquiterpenoids from Heterotheca inuloides [J].

Kubo, I ;

Chaudhuri, SK ;

Kubo, Y ;

Sanchez, Y ;

Ogura, T ;

Saito, T ;

Ishikawa, H ;

Haraguchi, H .

PLANTA MEDICA, 1996, 62 (05) :427-430

[8] PHENOLIC CONSTITUENTS OF CALIFORNIA BUCKEYE FRUIT [J].

KUBO, I ;

YING, BP .

PHYTOCHEMISTRY, 1992, 31 (11) :3793-3794

[9] Tyrosinase inhibitors from cumin [J].

Kubo, I ;

Kinst-Hori, I .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1998, 46 (12) :5338-5341

[10]

Lim JY, 1999, PHYTOTHER RES, V13, P371, DOI 10.1002/(SICI)1099-1573(199908/09)13:5&lt

← 1 2 3 →