Synthesis and Anti-Inflammatory Activities of Phloroglucinol-Based Derivatives

被引：23

作者：

Li, Ning ^{[1
,2
]}

Khan, Shabana I. ^{[1
,3
]}

Qiu, Shi ^{[1
]}

Li, Xing-Cong ^{[1
,3
]}

机构：

[1] Univ Mississippi, Sch Pharm, Nation Ctr Nat Prod Res, Res Inst Pharmaceut Sci, University, MS 38677 USA

[2] Anhui Med Univ, Sch Pharm, Hefei 230032, Anhui, Peoples R China

[3] Univ Mississippi, Sch Pharm, Dept Biomol Sci, University, MS 38677 USA

来源：

MOLECULES | 2018年 / 23卷 / 12期

关键词：

phlorogluciniol; acylphloroglucinol; anti-inflammatory; iNOS; NF-B; ACYLPHLOROGLUCINOL; CONSTITUENTS; INFLAMMATION;

D O I：

10.3390/molecules23123232

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：

The natural product phloroglucinol-based derivatives representing monoacyl-, diacyl-, dimeric acyl-, alkylated monoacyl-, and the nitrogen-containing alkylated monoacylphloro- glucinols were synthesized and evaluated for inhibitory activities against the inflammatory mediators such as inducible nitric oxide synthase (iNOS) and nuclear factor kappaB (NF-B). The diacylphloroglucinol compound 2 and the alkylated acylphloroglucinol compound 4 inhibited iNOS with IC50 values of 19.0 and 19.5 mu M, respectively, and NF-B with IC50 values of 34.0 and 37.5 mu M, respectively. These compounds may serve as leads for the synthesis of more potent anti-inflammatory compounds for future drug discovery.

引用

页数：8

共 26 条

[1]

Fukuyama T, 1969, Hinyokika Kiyo, V15, P818

[2] Biomimetic Synthesis of Polycyclic Polyprenylated Acylphloroglucinol Natural Products Isolated from Hypericum papuanum [J].

George, Jonathan H. ;

Hesse, Micha D. ;

Baldwin, Jack E. ;

Adlington, Robert M. .

ORGANIC LETTERS, 2010, 12 (15) :3532-3535

[3] Bioactive Acylphloroglucinols from Hypericum densiflorum [J].

Henry, Geneive E. ;

Campbell, Matthew S. ;

Zelinsky, Ashlee A. ;

Liu, Yunbao ;

Bowen-Forbes, Camile S. ;

Li, Liya ;

Nair, Muraleedharan G. ;

Rowley, David C. ;

Seeram, Navindra P. .

PHYTOTHERAPY RESEARCH, 2009, 23 (12) :1759-1762

[4] Anti-inflammatory activity of edible brown alga Eisenia bicyclis and its constituents fucosterol and phlorotannins in LPS-stimulated RAW264.7 macrophages [J].

Jung, Hyun Ah ;

Jin, Seong Eun ;

Ahn, Bo Ra ;

Lee, Chan Mi ;

Choi, Jae Sue .

FOOD AND CHEMICAL TOXICOLOGY, 2013, 59 :199-206

[5] IL-23 enhances the inflammatory cell response in Cryptococcus neoformans infection and induces a cytokine pattern distinct from IL-12 [J].

Kleinschek, MA ;

Muller, U ;

Brodie, SJ ;

Stenzel, W ;

Kohler, G ;

Blumenschein, WM ;

Straubinger, RK ;

McClanahan, T ;

Kastelein, RA ;

Alber, G .

JOURNAL OF IMMUNOLOGY, 2006, 176 (02) :1098-1106

[6] Hyperforin, an anti-inflammatory constituent from St. John's wort, inhibits microsomal prostaglandin E2 synthase-1 and suppresses prostaglandin E2 formation in vivo [J].

Koeberle, Andreas ;

Rossi, Antonietta ;

Bauer, Julia ;

Dehm, Friederike ;

Verotta, Luisella ;

Northoff, Hinnak ;

Sautebin, Lidia ;

Werz, Oliver .

FRONTIERS IN PHARMACOLOGY, 2011, 2

[7]

Kondo A, 1969, Hinyokika Kiyo, V15, P748

[8] Facile and efficient synthesis and herbicidal activity determination of novel 1,2,4-triazolo[4,3-a]pyridin-3(2H)-one derivatives via microwave irradiation [J].

Liu, Xing-Hai ;

Zhai, Zhi-Wen ;

Xu, Xiao-Yan ;

Yang, Ming-Yan ;

Sun, Zhao-Hui ;

Weng, Jian-Quan ;

Tan, Cheng-Xia ;

Chen, Jie .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (23) :5524-5528

[9] Can Phlorotannins Purified Extracts Constitute a Novel Pharmacological Alternative for Microbial Infections with Associated Inflammatory Conditions? [J].

Lopes, Graciliana ;

Sousa, Carla ;

Silva, Luis R. ;

Pinto, Eugenia ;

Andrade, Paula B. ;

Bernardo, Joao ;

Mouga, Teresa ;

Valentao, Patricia .

PLOS ONE, 2012, 7 (02)

[10] Synthesis of the acylphloroglucinols rhodomyrtone and rhodomyrtosone B [J].

Morkunas, Marius ;

Dube, Linda ;

Goetz, Friedrich ;

Maier, Martin E. .

TETRAHEDRON, 2013, 69 (40) :8559-8563

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