Synthesis and anti-inflammatory effects of a series of novel 9-O-substituted berberine derivatives

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• 作者：Zhenbao Liu ; Xiaohong Wang ; Hang Zhang ; Shanshan Zhang…
• 关键词：Berberine derivatives ; Carboxylic acid drug ; Anti ; inflammatory effects ; Ear swelling inhibition ; Cytokines
• 刊名：Medicinal Chemistry Research
• 出版年：2017
• 出版时间：March 2017
• 年：2017
• 卷：26
• 期：3
• 页码：672-679
• 全文大小：
• 刊物主题：Pharmacology/Toxicology; Biochemistry, general; Cell Biology;
• 出版者：Springer US
• ISSN：1554-8120
• 卷排序：26

文摘

Berberine owns multiple pharmacological activities, especially anti-inflammatory activity. To enhance the anti-inflammatory therapeutic efficiency of berberine, a series of novel 9-O-substituted berberine derivatives (5a–5d) were synthesized and their anti-inflammatory activities were evaluated. 13C-NMR, 1H-NMR, IR and high resolution mass spectrum (HRMS) results indicated that these derivatives were successfully synthesized. The xylene-induced inflammatory mice model demonstrated that these derivatives showed dose-dependent inhibition of ear inflammatory swelling. Comparing to berberine, ibuprofen and naproxen-modified berberine derivatives enhanced anti-inflammatory activities, while aspirin and nicotinic acid-modified berberine derivatives showed lower anti-inflammatory effects at the same dosages. This could be attributed to the enhanced inhibition of secretion of cytokines, including interleukin-6 and tumor necrosis factor-α, by ibuprofen and naproxen berberine derivatives, while aspirin and nicotinic acid berberine derivatives showed lower inhibition of tumor necrosis factor-α than berberine. These results suggest that ibuprofen and naproxen-modified berberine derivatives are promising new anti-inflammatory drug candidates.