Synthesis and structure-activity relationships of guaiane-type sesquiterpene lactone derivatives with respect to inhibiting NO production in lipopolysaccharide-induced RAW 264.7 macrophages

被引：15

作者：

Chen, Hao ^{[1
,2
]}

Chen, Bing-Yang ^{[2
]}

Liu, Chun-Ting ^{[2
]}

Zhao, Zeng ^{[2
]}

Shao, Wen-Hao ^{[2
]}

Yuan, Hu ^{[2
,3
]}

Bi, Kai-Jian ^{[2
]}

Liu, Jiang-Yun ^{[1
]}

Sun, Qing-Yan ^{[2
]}

Zhang, Wei-Dong ^{[1
,2
]}

机构：

[1] Soochow Univ, Sch Pharm, Suzhou 215123, Peoples R China

[2] Second Mil Med Univ, Sch Pharm, Shanghai 200433, Peoples R China

[3] Shanghai Jiao Tong Univ, Sch Pharm, Shanghai 200240, Peoples R China

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2014年 / 83卷

关键词：

Guaiane-type derivatives; Nitric oxide production; Inhibitory effect; Structure-activity relationship; INULA-JAPONICA; PHOTOCHEMICAL TRANSFORMATIONS; ALPHA-SANTONIN; DIABETIC MICE; AMINOGUANIDINE; CONSTITUENTS;

D O I：

10.1016/j.ejmech.2014.06.043

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A guaiane framework was scaffolded by photochemical rearrangement reactions using alpha-santonin 1 as a starting material. Then, using a series of reactions, we synthesized the guaiane-type sesquiterpene lactone 5 in high yield. The inhibitory activities of compound 5 and of a series of derivatives on nitric oxide (NO) release were evaluated in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. Compounds 6g, 7h, 7i, 7k and 8g, exhibited significant inhibitory effects on NO production, with IC50 values of 14.8, 22.3, 18.3, 17.4 and 7.0 mu M, respectively. Their cytotoxicities were also estimated using an MTT assay. The structure-activity relationships of these compounds were also discussed. (C) 2014 Elsevier Masson SAS. All rights reserved.

引用

页码：307 / 316

页数：10

共 25 条

[1] Insecticidal activity of sesquiterpenes skeleton synthesized by the conventional Robinson annulations reaction on Drosophila melanogaster [J].

Alarcon, Julio ;

Lamilla, Claudio ;

Cespedes, Carlos L. .

INDUSTRIAL CROPS AND PRODUCTS, 2013, 42 :268-272

[2] Synthesis and cytotoxic activity of α-santonin derivatives [J].

Arantes, Francisco F. P. ;

Barbosa, Luiz C. A. ;

Alvarenga, Elson S. ;

Demuner, Antonio J. ;

Bezerra, Daniel P. ;

Ferreira, Jose R. O. ;

Costa-Lotufo, Leticia V. ;

Pessoa, Claudia ;

Moraes, Manoel O. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (09) :3739-3745

[3] Regio- and stereoselective oxyfunctionalization at C-1 and C-5 in sesquiterpene guaianolides [J].

Bargues, V ;

Blay, G ;

Cardona, L ;

García, B ;

Pedro, JR .

TETRAHEDRON, 1998, 54 (09) :1845-1852

[4] PHOTOCHEMICAL TRANSFORMATIONS .2. THE CONSTITUTION OF LUMISANTONIN [J].

BARTON, DHR ;

DEMAYO, P ;

SHAFIQ, M .

JOURNAL OF THE CHEMICAL SOCIETY, 1958, (JAN) :140-146

[5] PHOTOCHEMICAL TRANSFORMATIONS .15. SYNTHETIC STUDIES ON GEIGERIN + ITS DERIVATIVES [J].

BARTON, DHR ;

WELLS, RJ ;

PINHEY, JT .

JOURNAL OF THE CHEMICAL SOCIETY, 1964, (AUG) :2518-&

[6] Synthesis of plagiochiline N from santonin [J].

Blay, G ;

Cardona, L ;

García, B ;

Lahoz, L ;

Pedro, JR .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) :7700-7705

[7] NITRIC-OXIDE PRODUCTION IN ISLETS FROM NONOBESE DIABETIC MICE - AMINOGUANIDINE-SENSITIVE AND AMINOGUANIDINE-RESISTANT STAGES IN THE IMMUNOLOGICAL DIABETIC PROCESS [J].

CORBETT, JA ;

MIKHAEL, A ;

SHIMIZU, J ;

FREDERICK, K ;

MISKO, TP ;

MCDANIEL, ML ;

KANAGAWA, O ;

UNANUE, ER .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (19) :8992-8995

[8] AMINOGUANIDINE, AN INHIBITOR OF INDUCIBLE NITRIC-OXIDE SYNTHASE, AMELIORATES EXPERIMENTAL AUTOIMMUNE ENCEPHALOMYELITIS IN SJL MICE [J].

CROSS, AH ;

MISKO, TP ;

LIN, RF ;

HICKEY, WF ;

TROTTER, JL ;

TILTON, RG .

JOURNAL OF CLINICAL INVESTIGATION, 1994, 93 (06) :2684-2690

[9] Phenylpropanoid glycosides from Scrophularia scorodonia:: In vitro anti-inflammatory activity [J].

Díaz, AM ;

Abad, MJ ;

Fernández, L ;

Silván, AM ;

De Santos, J ;

Bermejo, P .

LIFE SCIENCES, 2004, 74 (20) :2515-2526

[10] HIGHLY STEREOSELECTIVE TOTAL SYNTHESES OF (+)-PACHYDICTYOL-A AND (-)-DICTYOLENE, NOVEL MARINE DITERPENES FROM BROWN SEAWEEDS OF THE FAMILY DICTYOTACEAE [J].

GREENE, AE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (16) :5337-5343

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