Synthesis of the dibenzylbutane lignan LCA derivatives and evaluation of their anti-inflammatory activities

IF 2.6 4区 医学 Q3 CHEMISTRY, MEDICINAL Medicinal Chemistry Research Pub Date : 2024-10-31 DOI:10.1007/s00044-024-03332-x
Juan Zhang, Conghao Gai, Jing Wang, Xiaobin Zhuo, Yan Zou, Jishun Yang, Yan Song, Qingjie Zhao, Xiaoyun Chai
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Abstract

The roots of Litsea cubeba (Lour.) Pers have been used for the treatment of rheumatism. We previously extracted and isolated the natural product dibenzylbutane lignan LCA with anti-inflammatory activity. In the current study, using LCA as the lead compound, two series of LCA derivatives with an imide structure and butadiene structure were designed and synthesized. Among them, compounds 10c and 16a showed stronger inhibitory effects on LPS-induced NO and ROS production in RAW264.7 cells. Further study showed that compound 16a not only reduced the levels of inflammatory cytokines, including IL-6, TNF-α, and IL-1β, but it also significantly reduced the expression of iNOS and COX-2. Preliminary mechanism of action studies suggested that 16a exerts anti-inflammatory effects by inhibiting the NF-κB signaling pathway. Overall, our results suggest that compound 16a may be used as a promising anti-inflammatory drug to enrich the compound library. Further study into compound 16a could provide research ideas and methods for developing anti-inflammatory drugs.

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二苄基丁烷木脂素LCA衍生物的合成及其抗炎活性评价
Litsea cubeba (Lour)的根白藜芦醇已被用于治疗风湿病。我们先前提取并分离了具有抗炎活性的天然产物二苄基丁烷木脂素LCA。本研究以LCA为先导化合物,设计合成了两个系列的亚胺结构和丁二烯结构的LCA衍生物。其中化合物10c和16a对lps诱导的RAW264.7细胞NO和ROS的产生有较强的抑制作用。进一步研究表明,化合物16a不仅能降低炎性细胞因子IL-6、TNF-α、IL-1β水平,还能显著降低iNOS、COX-2的表达。初步作用机制研究表明,16a通过抑制NF-κB信号通路发挥抗炎作用。总之,我们的研究结果表明,化合物16a可能作为一种有前景的抗炎药物来丰富化合物库。进一步研究化合物16a可为抗炎药物的开发提供研究思路和方法。
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来源期刊
Medicinal Chemistry Research
Medicinal Chemistry Research 医学-医药化学
CiteScore
4.70
自引率
3.80%
发文量
162
审稿时长
5.0 months
期刊介绍: Medicinal Chemistry Research (MCRE) publishes papers on a wide range of topics, favoring research with significant, new, and up-to-date information. Although the journal has a demanding peer review process, MCRE still boasts rapid publication, due in part, to the length of the submissions. The journal publishes significant research on various topics, many of which emphasize the structure-activity relationships of molecular biology.
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