Flavonols from saffron flower: Tyrosinase inhibitory activity and inhibition mechanism

被引：234

作者：

Kubo, I ^{[1
]}

Kinst-Hori, I ^{[1
]}

机构：

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

来源：

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY | 1999年 / 47卷 / 10期

关键词：

Crocus sativus; kaempferol; flavonols; tyrosinase inhibitory activity; competitive inhibitor; copper chelator;

D O I：

10.1021/jf990201q

中图分类号：

S [农业科学];

学科分类号：

09 ;

摘要：

A common flavonol, kaempferol, isolated from the fresh flower petals of Crocus sativus L. (Iridaceae) was found to inhibit the oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA) catalyzed by mushroom tyrosinase with an ID50 Of 67 mu g/mL (0.23 mM). Interestingly, its 3-O-glycoside derivatives did not inhibit this oxidation. The inhibition kinetics analyzed by a Lineweaver-Burk plot found kaempferol to be a competitive inhibitor, and this inhibitory activity presumably comes from its ability to chelate copper in the enzyme. This copper chelation mechanism can be applicable for all of the flavonols as long as their 3-hydroxyl group is free. However, quercetin, kaempferol, and galangin each affect the oxidation of L-tyrosine in somewhat different ways.

引用

页码：4121 / 4125

页数：5

共 39 条

[31] INFLUENCE OF ACID AND BASE HYDROLYSIS ON THE PHENOLIC COMPOSITION OF RED RASPBERRY JUICE [J].

ROMMEL, A ;

WROLSTAD, RE .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1993, 41 (08) :1237-1241

[32]

SANCHEZFERRER A, 1995, BBA-PROTEIN STRUCT M, V1247, P1

[33] STABILITY OF FLAVONOID COMPLEXES OF COPPER(II) AND FLAVONOID ANTIOXIDANT ACTIVITY [J].

THOMPSON, M ;

WILLIAMS, CR .

ANALYTICA CHIMICA ACTA, 1976, 85 (02) :375-381

[34] ANTIOXIDANT ACTIVITY OF FLAVONOIDS AND REACTIVITY WITH PEROXY RADICAL [J].

TOREL, J ;

CILLARD, J ;

CILLARD, P .

PHYTOCHEMISTRY, 1986, 25 (02) :383-385

[35] Sequence and structural features of plant and fungal tyrosinases [J].

VanGelder, CWG ;

Flurkey, WH ;

Wichers, HJ .

PHYTOCHEMISTRY, 1997, 45 (07) :1309-1323

[36] PLANT FLAVONOIDS, ESPECIALLY TEA FLAVONOLS, ARE POWERFUL ANTIOXIDANTS USING AN IN-VITRO OXIDATION MODEL FOR HEART-DISEASE [J].

VINSON, JA ;

DABBAGH, YA ;

SERRY, MM ;

JANG, JH .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1995, 43 (11) :2800-2802

[37]

Whitaker JR., 1995, FOOD ENZYMES STRUCTU, P271, DOI DOI 10.1007/978-1-4757-2349-6_9

[38] SUBSTRATE-ANALOG BINDING TO THE COUPLED BINUCLEAR COPPER ACTIVE-SITE IN TYROSINASE [J].

WILCOX, DE ;

PORRAS, AG ;

HWANG, YT ;

LERCH, K ;

WINKLER, ME ;

SOLOMON, EI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :4015-4027

[39] INHIBITORY EFFECTS OF FLAVONOL GLYCOSIDES ON 12-0-TETRADECANOYLPHORBOL-13-ACETATE-INDUCED TUMOR PROMOTION [J].

YASUKAWA, K ;

TAKIDO, M ;

TAKEUCHI, M ;

SATO, Y ;

NITTA, K ;

NAKAGAWA, S .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (03) :774-776

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