Molecular design of antibrowning agents: antioxidative tyrosinase inhibitors

被引：115

作者：

Kubo, I ^{[1
]}

Chen, QX ^{[1
]}

Nihei, K ^{[1
]}

机构：

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

来源：

FOOD CHEMISTRY | 2003年 / 81卷 / 02期

关键词：

antibrowning; tyrosinase inhibitory activity; dodecyl gallate;

D O I：

10.1016/S0308-8146(02)00418-1

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Dodecyl (C-12) gallate (3,4,5-trihydroxybenzoate) was found to inhibit the oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA) catalyzed by tyrosinase. This inhibition is a slow and reversible reaction with residual enzyme activity. The inhibition kinetics analyzed by Lineweaver-Burk plots revealed that dodecyl (lauryl) gallate is an uncompetitive inhibitor (K-IS=0.636 mM). Gallic acid, the parent compound of dodecyl gallate, acts as a reducing agent for o-quinone produced by the enzymic oxidation. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：241 / 247

页数：7

共 22 条

[1] EVALUATION OF THE ANTIOXIDANT AND PROOXIDANT ACTIONS OF GALLIC ACID AND ITS DERIVATIVES [J].

ARUOMA, OI ;

MURCIA, A ;

BUTLER, J ;

HALLIWELL, B .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1993, 41 (11) :1880-1885

[2] Kinetics of inhibition of β-glucosidase from Ampullarium crossean by bromoacetic acid [J].

Chen, QX ;

Zhang, Z ;

Zhou, XW ;

Zhuang, ZL .

INTERNATIONAL JOURNAL OF BIOCHEMISTRY & CELL BIOLOGY, 2000, 32 (07) :717-723

[3] Food browning and its prevention: An overview [J].

Friedman, M .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1996, 44 (03) :631-653

[4] LINEAR RELATIONSHIPS BETWEEN LIPOPHILIC CHARACTER AND BIOLOGICAL-ACTIVITY OF DRUGS [J].

HANSCH, C ;

DUNN, WJ .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1972, 61 (01) :1-&

[5] INHIBITION STUDIES ON APPLE POLYPHENOL OXIDASE [J].

JANOVITZKLAPP, AH ;

RICHARD, FC ;

GOUPY, PM ;

NICOLAS, JJ .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1990, 38 (04) :926-931

[6] Tyrosinase inhibitors from anise oil [J].

Kubo, I ;

Kinst-Hori, I .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1998, 46 (04) :1268-1271

[7] Molecular design of antibrowning agents [J].

Kubo, I ;

Kinst-Hori, I ;

Kubo, Y ;

Yamagiwa, Y ;

Kamikawa, T ;

Haraguchi, H .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2000, 48 (04) :1393-1399

[8]

Kubo I, 1999, CHEMTECH, V29, P37

[9] Antifungal activity of octyl gallate: Structural criteria and mode of action [J].

Kubo, I ;

Xiao, P ;

Fujita, K .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (03) :347-350

[10]

MAYER AM, 1987, PHYTOCHEMISTRY, V26, P11

← 1 2 3 →