New jasmonate analogues as potential anti-inflammatory agents

被引：53

作者：

Dang, Hung The ^{[1
]}

Lee, Hye Ja ^{[2
]}

Yoo, Eun Sook ^{[2
]}

Hong, Jongki ^{[3
]}

Bao, Baoquan ^{[1
]}

Choi, Jae Sue ^{[4
]}

Jung, Jee H. ^{[1
]}

机构：

[1] Pusan Natl Univ, Coll Pharm, Pusan 609735, South Korea

[2] Jeju Natl Univ, Coll Med, Cheju, South Korea

[3] Kyung Hee Univ, Coll Pharm, Seoul, South Korea

[4] Pukyong Natl Univ, Fac Food Sci & Biotechnol, Pusan, South Korea

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2008年 / 16卷 / 24期

关键词：

Methyl jasmonate; Anti-inflammatory activity; Enone functionality; Cytokine;

D O I：

10.1016/j.bmc.2008.10.050

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：

In an effort to develop new anti-inflammatory agents, methyl jasmonate analogues (2-20) were synthesized and evaluated for their inhibitory effects on the production of pro-inflammatory mediators (NO, IL-6, and TNF-alpha) in lipopolysaccharide (LPS)-activated RAW264.7 murine macrophage cells. The introduction of an enone functionality to the structure of a plant hormone ( 1) rendered the product (2) a significant anti-inflammatory activity. Analogues further derived from 2 (7, 9, 13, and 15) exhibited even more enhanced activity, and these compounds were much more potent than natural anti-inflammatory prostaglandins (PGA(1), PGA(2), and 15-deoxy-Delta(12,14)-PGJ(2)). Among them, compounds 9 and 15 showed the highest potency, while compounds 7 and 13 would be more desirable with respect to safety. This is the first study demonstrating the anti-inflammatory potential of jasmonate derivatives, and the present results suggest that alpha-haloenone jasmonates (7, 9, 13, and 15) may serve as potential anti-inflammatory leads. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：10228 / 10235

页数：8

共 56 条

[1]

BACOPOULOS NG, 2008, Patent No. 08007367

[2] 2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate as an efficient coupling reagent for the amidation and phenylhydrazation of carboxylic acids at room temperature [J].

Balalaie, S. ;

Mahdidoust, M. ;

Eshaghi-Najafabadi, R. .

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2007, 4 (03) :364-369

[3]

Beunard J. L., 2001, ANGEW CHEM, V113, P4881

[4] MACROLACTONIZATION-TRANSANNULAR ALDOL CONDENSATION APPROACH TO THE TAXANE AB RING-SYSTEM [J].

CHAI, KB ;

SAMPSON, P .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (24) :6807-6813

[5] In vitro anti-inflammatory effects of cynaropicrin, a sesquiterpene lactone, from Saussurea lappa [J].

Cho, JY ;

Baik, KU ;

Jung, JH ;

Park, MH .

EUROPEAN JOURNAL OF PHARMACOLOGY, 2000, 398 (03) :399-407

[6] Anti-inflammatory constituents of the red alga Gracilaria verrucosa and their synthetic analogues [J].

Dang, Hung The ;

Lee, Hye Ja ;

Yoo, Eun Sook ;

Shinde, Pramod B. ;

Lee, Yoon Mi ;

Hong, Jongki ;

Kim, Dong Kyoo ;

Jung, Jee H. .

JOURNAL OF NATURAL PRODUCTS, 2008, 71 (02) :232-240

[7] Plant stress hormones suppress the proliferation and induce apoptosis in human cancer cells [J].

Fingrut, O ;

Flescher, E .

LEUKEMIA, 2002, 16 (04) :608-616

[8] Jasmonates - a new family of anti-cancer agents [J].

Flescher, E .

ANTI-CANCER DRUGS, 2005, 16 (09) :911-916

[9]

FLESCHER E, 2002, Patent No. 6469061

[10] Jasmonates in cancer therapy [J].

Flescher, Eliezer .

CANCER LETTERS, 2007, 245 (1-2) :1-10

← 1 2 3 4 5 6 →