3-HYDROXYCOUMARINS - 1ST DIRECT PREPARATION FROM COUMARINS USING A CU-2+ ASCORBIC-ACID O2 SYSTEM, AND THEIR POTENT BIOACTIVITIES

被引：18

作者：

AIHARA, K ^{[1
]}

HIGUCHI, T ^{[1
]}

HIROBE, M ^{[1
]}

机构：

[1] UNIV TOKYO,FAC PHARMACEUT SCI,HONGO 7-3-1,BUNKYO KU,TOKYO 113,JAPAN

来源：

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS | 1990年 / 168卷 / 01期

关键词：

D O I：

10.1016/0006-291X(90)91689-P

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：

First direct 3-hydroxylation of a coumarin ring via a purely chemical system, previously only possible using cytochrome P-450, was successfully conducted by a Cu2+-ascorbic acid-O2 system; the two 3-hydroxycoumarins obtained were novel compounds, 3-hydroxyscopoletin and 3-hydroxyisoscopoletin. 5-Lipoxygenase and α-D-glucosidase inhibitory activities of coumarins greatly increased through 3-hydroxylation. 3-Hydroxyscopoletin and 3-hydroxyumbelliferone had a high inhibitory potency for 5-lipoxygenase and for α-D-glucosidase respectively; they serve as lead compounds for new drugs. © 1990.

引用

页码：169 / 175

页数：7

共 31 条

[1]

AIHARA K, 1988, CHEM PHARM BULL, V36, P837

[2] VITAMIN-C PREFERENTIAL TOXICITY FOR MALIGNANT-MELANOMA CELLS [J].

BRAM, S ;

FROUSSARD, P ;

GUICHARD, M ;

JASMIN, C ;

AUGERY, Y ;

SINOUSSIBARRE, F ;

WRAY, W .

NATURE, 1980, 284 (5757) :629-631

[3] SELECTIVE ORTHO-HYDROXYLATION OF PHENOLS .2. A NEW CATALYTIC-SYSTEM OF PREPARATIVE CHARACTER [J].

CAPDEVIELLE, P ;

MAUMY, M .

TETRAHEDRON LETTERS, 1982, 23 (15) :1577-1580

[4] SELECTIVE ORTHO-HYDROXYLATION OF PHENOLS .1. TOWARDS A SIMPLE CHEMICAL-MODEL OF TYROSINASE [J].

CAPDEVIELLE, P ;

MAUMY, M .

TETRAHEDRON LETTERS, 1982, 23 (15) :1573-1576

[5] SPECIFIC CLEAVAGES OF DNA BY ASCORBATE IN THE PRESENCE OF COPPER-ION OR COPPER-CHELATES [J].

CHIOU, SH ;

CHANG, WC ;

JOU, YS ;

CHUNG, HMM ;

LO, TB .

JOURNAL OF BIOCHEMISTRY, 1985, 98 (06) :1723-1726

[6]

FEUER G, 1970, Chemico-Biological Interactions, V2, P203, DOI 10.1016/0009-2797(70)90023-2

[7]

GIBSON GG, 1986, INTRO DRUG METABOLIS

[8] CATECHOL ESTROGEN FORMATION BY BRAIN-TISSUE - CHARACTERIZATION OF A DIRECT-PRODUCT ISOLATION ASSAY FOR ESTROGEN-2-HYDROXYLASE AND 4-HYDROXYLASE ACTIVITY AND ITS APPLICATION TO STUDIES OF 2-HYDROXYESTRADIOL AND 4-HYDROXYESTRADIOL FORMATION BY RABBIT HYPOTHALAMUS [J].

HERSEY, RM ;

WILLIAMS, KIH ;

WEISZ, J .

ENDOCRINOLOGY, 1981, 109 (06) :1912-1920

[9] CATECHOL ESTROGEN FORMATION BY BRAIN-TISSUE - A COMPARISON OF THE RELEASE OF TRITIUM FROM [2-H-3] ESTRADIOL WITH [6,7-H-3]2-HYDROXYESTRADIOL FORMATION FROM [6,7-H-3]-LABELED ESTRADIOL BY RABBIT HYPOTHALAMI INVITRO [J].

HERSEY, RM ;

GUNSALUS, P ;

LLOYD, T ;

WEISZ, J .

ENDOCRINOLOGY, 1981, 109 (06) :1902-1911

[10]

HIROBE M, 1988, CHEM RESOURCES NEW D, P234

← 1 2 3 4 →