Syntheses of ferulic acid derivatives and their suppressive effects on cyclooxygenase-2 promoter activity

被引：68

作者：

Hosoda, A

Ozaki, Y

Kashiwada, A

Mutoh, M

Wakabayashi, K

Mizuno, K

Nomura, E

Taniguchi, H

机构：

[1] Ind Technol Ctr Wakayama Prefecture, Wakayama 6496261, Japan

[2] Japan Sci & Technol Corp, Kawaguchi 3320012, Japan

[3] Natl Canc Ctr, Res Inst, Canc Prevent Div, Tokyo 1040045, Japan

[4] Univ Osaka Prefecture, Coll Engn, Dept Appl Chem, Osaka 5998531, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2002年 / 10卷 / 04期

关键词：

D O I：

10.1016/S0968-0896(01)00386-8

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：

Novel ferulic acid derivatives in which feruloyl groups were attached to the hydroxyl groups of myo-inositol 1,3,5-orthoformate derivatives were synthesized. These feruloyl-myo-inositols suppressed the cyclooxygenase-2 (COX-2) promoter activity in a concentration-dependent manner. Among the examined compounds, compound 4 showed the highest activity. A treatment with 100 muM of compound 9 for 24 h resulted in a 50% decrease of COX-2 promoter activity without marked cytotoxicity. Both the molecular structure in which two ferulic acid moieties are facing each other and the molecular hydrophobicity may be essential for the suppression of COX-2 promoter activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1189 / 1196

页数：8

共 46 条

[1] INOSITOL TRISPHOSPHATE AND CALCIUM SIGNALING [J].

BERRIDGE, MJ .

NATURE, 1993, 361 (6410) :315-325

[2] INOSITOL TRISPHOSPHATE, A NOVEL 2ND MESSENGER IN CELLULAR SIGNAL TRANSDUCTION [J].

BERRIDGE, MJ ;

IRVINE, RF .

NATURE, 1984, 312 (5992) :315-321

[3]

Beurskens P. T., 1994, DIRDIF 94 PROGRAM SY

[4] From indomethacin to a selective COX-2 inhibitor: Development of indolalkanoic acids as potent and selective cyclooxygenase-2 inhibitors [J].

Black, WC ;

Bayly, C ;

Belley, M ;

Chan, CC ;

Charleson, S ;

Denis, D ;

Gauthier, JY ;

Gordon, R ;

Guay, D ;

Kargman, S ;

Lau, CK ;

Leblanc, Y ;

Mancini, J ;

Ouellet, M ;

Percival, D ;

Roy, P ;

Skorey, K ;

Tagari, P ;

Vickers, P ;

Wong, E ;

Xu, L ;

Prasit, P .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (06) :725-730

[5]

Clifford MN, 1999, J SCI FOOD AGR, V79, P362, DOI [10.1002/(SICI)1097-0010(19990301)79:3&lt

[6]

362::AID-JSFA256&gt

[7]

3.0.CO

[8]

2-D, 10.1002/(SICI)1097-0010(19990301)79:3<362::AID-JSFA256>3.0.CO

[9]

2-D]

[10] Increased cyclooxygenase-2 levels in carcinogen-induced rat colonic tumors [J].

DuBois, RN ;

Radhika, A ;

Reddy, BS ;

Entingh, AJ .

GASTROENTEROLOGY, 1996, 110 (04) :1259-1262

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